Paulina

By Devianti Gusti

Published on Jun 6, 2020

Transgender

Continuing the adventures of Paulina, the cross-dressing boy.

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Some background

The context of this story will make more sense if you read "Paulina and the Gentleman", to be published soon.

Be patient, as this one starts out slow but does get hot after a while.

More stories featuing Paulina: "Making Money With Mr. Jack". She is a little younger in that one. "Getting the Dishwasher Fixed". Set a few weeks after giving her virginity.

If you havent read the other story, here are the main characters:

Paulina: 15, crossdressing boy. Pretty, Italian looks. Bernard: 41, friend of stepdad. Paulina met him previously at one of her parent's parties. Jan: 21, friend of parents and Pauliina Dawn, Shawn: Early 30's. Parent's friends Paulina is closest to Ann, Joe(Pervert), Jonny, Rick: All mid 20's. Other family friends Senegal/Tina: 15, close girl friend from school Beth: 20, Paulina's sister abused and driven away by their mother Marie: Paulina's mother Hank: Paulina's stepdad

Paulina Gives her Virginity

Over a week had passed since spending time with Bernie at the party my parents had on the previous Saturday. Wednesday night he called me.

"Hi Little Girl, how are you?"

"Hi Daddy! I was hoping you would call me." I was very excited to hear from him.

"I've been busy, but I said I would."

"I knew you would. I had no doubts."

"So, would you still like to come over? Are you free tomorrow afternoon?

"Yes, I would! I'm free for the whole evening. Can you pick me up at my neighbor's house up the street like we talked about?"

"Of course. Would 5:00 work?"

"Yes. Here's his address. I'll be standing at the end of his driveway." I gave him the house number.

"Okay, it's a date. Have you seen my car? It's a silver Thunderbird. I'll be there at five."

"I'll see you then, Daddy." I gave him a big smooch.

"Looking forward to seeing you, Little Girl. Have a good night."

I was so excited that I was going to see him the next day. A real adult date! I didn't want to wait until the weekend to tell her, so I called Jan.

"Hey Jan! How are you?"

"Hey Paulina. I'm cool. You sound happy. What's going on?"

"Remember I told you that I was gonna see Bernie again? Well, I'm gonna spend tomorrow evening with him. We're gonna have a date. Like a real date!"

"Paulina! You naughty girl!"

Jeff heard my name. "Hey, you fox!" he hollered from across the room.

"Tell him hey. Do you two live together? I never asked before."

"Yeah, he moved in with me a little while back. Sorry I didn't mention it. Anyway, you were saying?"

"Oh. Well, he's picking me up and we're going to his place. He lives on The Point."

"Where is he picking you up? Not your house, huh? Not sure how you'd explain that to your dad."

"I know. He's picking me up at one of the people's house that I do work for."

"Oh. You mean your...special work?" she said playfully.

"It's not all the time!" I replied. "But yeah, one of them. He's a super nice guy. He's older than Bernie. Very handsome and distinguished as well."

"Of course he is. Why am I not surprised!" We both laughed at this.

"He's super, super nice. His wife died like two years ago, and they never had kids, so he lives alone now. I go clean his house and do his laundry, and stuff like that."

"And?"

"Well...sometimes, we, um, play a little bit." I giggled.

"And he pays you extra when you do?"

"Yeah. He's very generous. I really appreciate it when he does."

"So, what do y'all do?"

"We, um, touch and feel each other. He, um, taught me how to give a handjob."

"Ah, so that's where you learned how. Do anything else?"

"Not really. Well, I do let him rub his dick on my panties till he cums sometimes. It feels so good!"

"Like from behind? Like he's fucking you?" She sounded excited but was trying to keep her voice down. She didn't want Jeff to hear what we were talking about.

"Yeah. But I keep my panties on so he can't stick it in. Sometimes he'll stop humping me and use his hand. Before he cums, I'll pull my panties down a little so he can cum all over my ass. I love it! He cums a lot! It's so hot and thick. I usually scoop up as much as I can and eat it. He says it's sexy watching me do that."

"I bet. I love feeling a guy cum, too. What else?"

"Once, he let me clean the head off after with my tongue. But I haven't sucked it yet."

"Oh. Maybe one day though, huh?"

"Yep. It's gonna be fun, too. His dick is really nice. It looks like Bernie's" I giggled and blushed.

"And do you call him Daddy too?"

"No, just Mister Jack. Ooops! I didn't mean to say that! You can't ever mention his name. Promise!"

"Don't worry, I promise not to say anything. So, how much does he give you?"

"When we don't play and I just do regular things, he'll give me ten or fifteen dollars. But when we do mess around, he usually gives me forty or fifty."

"What?!? Are you serious? That's a lot! And he's not even fucking you!"

"I know, and I told him he doesn't have to give me so much. I kinda feel bad when he gives me that much when we only fool around a little bit."

"Don't feel that way. You take as much as he wants to give you. You might not think you're doing a lot, but believe me, it's a lot. Just because."

"Because I'm fifteen?"

"Yes. So you let him pay you however much he wants, okay?"

"Okay. I'll try not to feel bad about it."

"Good. Don't. So, back to your date with Daddy" she giggled, "What are y'all gonna do all evening?"

"I think we're gonna eat, and maybe have a drink. We'll probably make out after...and maybe other things" I said coyly.

"And what kind of other things, you naughty girl?!?"

"Um, maybe he'll, um, let me suck it."

"Oooh! You said he has a big one and cums a lot, huh? Sounds good."

"He does, and it tastes good! I can't wait!" I giggled.

"So how many blowjobs have you given?"

"Um...none."

"What?!? You want to go in your dad's office with me, but you've never done it before?" She was really surprised.

"Um, yeah. So, I want to learn how to do it right, and I know Bernie 'll teach me good. He's real patient and I know he'll let me go real slow and get it right."

"Yeah, I get the feeling you're not the only one he's taught how to suck him off. Or more."

"I know. He told me he's had young girls all over the world, and that they're his favorite. That's so cool!"

"You're an interesting one, Paulina. Like we talked about before, most people don't approve of the age thing. And I don't think most women would like hearing about how many young girls he's been with. Or adult women, for that matter."

"But it's exciting to know that he has so much experience. I can try to imagine what each one would be like. Ummm!"

"Well, you're gonna have to call me after and tell me all about it!"

"Okay, I will. I can't wait!"

"I know. I can tell! Alright sweetie, let me go. Don't forget to call me when you get home."

"I won't. Ciao!"

My school day passed in a blur. My friends knew I was excited about something but I didn't tell any of them. I couldn't wait to get home. I rode quickly, waving to people I knew. Arriving home, I parked my bike on the back patio and went inside. My turtle was hungry, so I got him some shrimp. Back inside, I saw that my stepdad was not in. I decided I could take a shower and change, and I would be gone before he was there to ask any questions.

I stripped as soon as I got in my room. Putting on my terrycloth robe, I went to the bathroom and started the shower. I got in and let my hair get thoroughly wet. The hot water felt good, relaxing my shoulders and neck. I wasn't sore or stiff, just tense from excitement.

As I washed my thick, coffee-brown hair, I noticed that it was getting longer. It fell just below my shoulders. I decided to let it grow about an inch more before getting it cut.

After conditioning and rinsing it out, I hopped out and dried off. I towel-dried it and brushed it out. I liked the wet look, so I didn't blow dry it. It looked nice down, so I did not pull it up into a ponytail.

For my lips, I couldn't decide between the lighter pink or the deeper coral color. Since I had painted my nails the coral a few days before, I went with the matching lipstick.

Finished in the bathroom, it was time to pick out clothes. I chose a white skirt that I didn't wear often. It was kind of short, and it made my ass look good. I chose a dark purple top that had a deep v neck, which showed a lot of skin on my chest. It was cut for a girl with either small boobs or a flat chest, so it looked good on me. A pair of purple leather sandals rounded out the outfit. I bought them to match the top but didn't wear them often.

A touch of perfume on each wrist finished my preparations. Giving myself a last once-over in the mirror, I was pleased how I looked and was ready to go. I knew Bernie would as well. Before leaving, I slipped the tube of KY into my purse. I locked the door behind me.

As I walked down the street, I hoped my stepdad would not drive by and notice me on his way home. Luckily, he wouldn't be home for a few hours. I made it to Jack's house and waited at the end of the driveway.

It wasn't long before Bernie pulled up. His car was a sharp looking silver Thunderbird Turbo. It was less than a year old and still had that new car smell. The leather seats were very comfortable, feeling cool under my bare legs.

I leaned over and gave him a hug and a kiss.

"Hi Daddy! I'm so glad you came to pick me up!"

"Hello, Little Girl. How are you today? You look very nice, and you smell great, too."

"Thanks. I'm glad you think so" I said with a blush.

"I really like your hair down. It's so thick and luxurious" he said smoothly.

I twirled the ends with my fingers. "Thanks, Daddy. I like to wear it down, but it gets so hot sometimes. I don't want to sweat too much, so that's why I usually put it up in a ponytail."

"It looks nice either way." He reached over and stroked it a bit. I couldn't hold in an `mmm'.

"So, my dear, I thought that we would have Italian for dinner." He gave me a hungry look.

I caught his innuendo.

"Daddy, you know I'm Italian..." I giggled.

"I know, Little Girl. I know" he said with a knowing smile, glad that I got what he said.

He rested a hand on my thigh as we drove. I shivered at first, but then felt the warmth of his skin on mine. It felt good and I looked forward to more.

Pulling up to his house, I sat and stared for a moment before getting out. His house was a very old Italianate Creole Cottage. With four windows across the front, it looked like a double, but it wasn't. The exterior was a deep olive color, with cream colored trim. A restoration must have been done recently, as the house looked new. I couldn't wait to see the inside.

Opening the car door, Bernie took my hand and helped me out. He led me onto the porch and unlocked the door.

Stepping inside, I had to catch my breath and not let my mouth hang open. I was inside the most beautiful house I had ever been in. The wood floors were stained a deep ebony. The plaster living room walls were a golden color while the dining room was a pale green. The ceilings were a shade lighted than the trim color on the outside.

The furniture was mostly antique, with many pieces bought on his travels to Europe. A large authentic Oriental rug covered the floor in the living room. It took me a moment to notice the high-end stereo system inside of an antique china cabinet. The speakers were discreetly located in the corners of the room. Classic jazz was playing at a low volume.

"Ohmygod, Bernie. Your house is beautiful! I've never been in a house like this before. It's like a museum. I don't want to touch anything!"

"Thanks. It took a lot of work to bring it back and make it better than it was. It still looks old, but its modern on its insides. But it's not a museum, so you can touch anything you like. The furniture's meant to be used."

"Okay, if you say so. Can I see the rest?"

"Sure." He walked me through the rest of the house, which was as beautiful as the front rooms.

"I'm just blown away. Everything's so nice!"

"I'm glad you like it. I love having this to come back to when I've been traveling."

"I can see why. I'm jealous."

"Time to eat, my dear. Want to help bring everything out?"

"Of course. What can I do?"

"If you get the bread and the salad, I'll get the rest."

We went into the kitchen, which was up to date with the latest appliances. I liked that there was almost nothing that was white. The tiled floors and backsplash had many colors and patterns, all fitting together well.

The bread and salad were on the counter. I brought them to the dining room table. It was large, made of a beautiful dark wood. The places were set and ready. The centerpiece was a large, beautiful bouquet of Spring flowers.

He brought out a chilled bottle of wine and two glasses.

"Do you drink wine yet? I know you like a Vodka Seven" he said with a wink.

"Actually, I've had red wine before. It was from France, but I can't remember what it was called."

"Did you like it?"

"It took me a little while, but I did like it."

He poured two glasses.

"I hope you like this, then. It's called Chianti, from Italy."

"To go with Italian food?"

"Exactly. You're pretty perceptive, Little Girl." He looked pleased with me.

"I want to learn all I can about things like this. Plus, I love Italian food. I've just had regular things though, like spaghetti and lasagna."

"You're in for a treat, then. I made us authentic chicken caccatori, with zucchini and yellow squash from my garden."

"You cook and you garden?" I was very impressed.

"I do cook, but I hired a nice lady to take care of my garden."

Handing me a wine glass, I raised it up to meet his.

"Salute!" we said at the same time as we clinked glasses.

I remembered what Jack taught me about how to taste wine. I swished it around first, inhaling the scent as I sipped it. I let it reach every part of my mouth before swallowing, in order to taste each subtle flavor.

It was different than the French wine, but very good.

Bernie watched as I tried the wine. He was impressed that I knew how to properly taste it.

"You do that well. Someone who knows how to drink wine must have taught you how."

"Yeah – I mean yes." I needed to remember my ladylike manners. "A neighbor, whose house you picked me up at, let me try wine for the first time. He showed me how to do it correctly."

"Well, you surely didn't learn it from your mother!" We both laughed hard.

"I tasted that cheap pink stuff she drinks. It wasn't good at all. But it is her, so." I made a sour face.

"I know. I tease her before" he said with a grin. "I told her she wouldn't know good wine if she fell into a barrel of it."

"Don't let her do that – the whole barrel will be ruined!" We laughed again.

Since my first glass was for tasting, it didn't contain much. He raised the bottle and nodded it towards me.

"Would you like a full glass this time?"

"Please" I answered with a sweet smile.

He filled it up halfway and topped off his own.

The salad was fresh, and the bread was warm. A delicious scent filled the room when he brought out the chicken caccatori and squash.

We talked and laughed as we ate, He told more stories of his travels, which I loved. He kept the wine flowing and never let it reach the bottom of our glasses. Despite the delicious food, I was tipsy before I knew it.

Taking a break from the wine, we each had a couple glasses of water. He said we needed to pace ourselves. I remembered what happened to Rick when one didn't.

Dessert was Napolean pastries and gelato from Brocato's. I found that the wine went with them as well.

We finished eating and cleared the table.

"Bernie, that was delicious! I can't remember the last time I ate something so good. You're like a chef."

"Thank you, Paulina. I'm glad you liked it. I really enjoy cooking, but rarely have anyone to cook for."

"I'll come eat anytime you want me to!" I said with a giggle.

He refilled our glasses and we clinked them together again, with another `Salute!'

"Let's sit and relax." He took my hand and led me to the couch in the living room. It was obviously a very old antique, and probably worth a lot of money. I was surprised at how comfortable it was to sit on, though I wasn't sure it would feel great if one fell asleep on it.

He took my glass and set it on the coffee table with his. He moved one of my hands to his thigh and rested his on top of it.

"So, Little Girl, here we are, just the two of us."

I gave him a dreamy, tipsy smile.

"I know. Thanks for letting me be with you. It means a lot. I really appreciate how sweet you are to me."

"You're very welcome. Like I told you before, I really like your company. You remind me to stay young. And it doesn't hurt that you're gorgeous!"

I blushed heavily. "I, um, I was afraid that you wouldn't want to see me again, unless you came to my house for another party."

"Why, dear?"

"Because...I'm, um, so young. I'll just be sixteen in August." I gave him a little pout.

He reached over and caressed my chin. "I was telling you the truth when I said I like young girls such as yourself. I always have. Your youth and freshness is...intoxicating."

"And I love the attention of older, distinguished gentlemen like yourself. I really do. You don't treat me like a child. I may only be fifteen, but I feel so much older inside."

"I noticed that about you before you introduced yourself to me. Mike told me good things about you since you were a young little boy."

"Mike's a great guy and he's always been nice to me. I'm glad I didn't disappoint you."

"Not in the least. In fact, I'm more impressed with you than some of the women I've met in their 20s and 30s."

"Really?" I was genuinely surprised.

"Yes, really. You're genuine and comfortable being yourself. You truly mean everything you say, and you say it with conviction. Especially when it has to do with others."

"I do. I really care for people and want to do whatever I can to make them feel good. I learned when I was little that most people don't feel the same way." I tried not to frown.

"That, my dear, is one of the best qualities anyone could ever have. Truly."

I almost got teary eyed as he complimented me. This was galaxies beyond just telling my how beautiful and sexy I looked. It was about me, not how I looked.

"Th-thank you. That really means a lot. I don't usually hear things like that about me. Usually its about how pretty I am, or how smart."

"Well, you are extremely beautiful and sexy, too. Being smart puts the cherry on top."

I blushed again.

"More?" He held up the bottle.

"Please." He filled my glass.

We sat quietly for a few moments, looking at each other and smiling. I was feeling so good and warm inside. I was probably almost drunk, but I hadn't felt this good since Shirley took care of me. It was similar but different. Wonderful all the same.

A mischievous look crossed his face. He put his wine glass down and stood up.

"Stay right here, Little Girl. I'll be right back."

I thought he needed to use the bathroom.

He returned quickly and looked to be holding something behind his back.

"I want you to close your eyes and hold out your left hand."

"Yes, Daddy." I did as he asked.

I felt something cool and metallic slip over my wrist. It quickly warmed up to match the temperature of my skin.

"Open your eyes and tell me what you think."

Circling my wrist was a 14 karat gold bangle bracelet. One section had gemstones set in it. Seven medium sized peridots were flanked by four smaller diamonds on either side. It looked to be a vintage piece of jewelry.

I was speechless for a moment. I could not believe he would give me something like this.

"F-for me? A-are you sure? This looks really expensive!"

"Yes, Little Girl. It's a gift for you" he said sweetly.

I felt another tipsy emotional swing. I couldn't stop the tears this time. But they were happy tears.

"Dadd- Bernie...I, um, don't know what to say. I-I mean thank you so much! It's beautiful. I love it!" I stood up and gave him a tight hug. "Th-this is the nicest thing anyone's ever given me."

He hugged me tight and kissed the top of my head.

"As soon as I saw it, I knew you would like it. It's beautiful, like you, but not gaudy and over the top."

"Th-these are peridot. That's my birthstone! How'd you know?" I asked as I turned it around my wrist.

"You did mention that your birthday was in August. So, I asked Hank. And he told me the day. I looked up the birthstone and they matched. Voila! You know what else? The jeweler told me it's Italian, just like you. How fitting!" he said with a big smile.

I was so happy at the moment that I could have burst. I truly loved the bracelet. More importantly, I loved that he thought enough of me to get such a thoughtful gift. He didn't just see something pretty and buy it.

I stopped fondling it long enough to take a long sip of wine.

"I. LOVE. IT!!!"

I wrapped my arms around his neck and pulled him into a kiss. It started out sweet but quickly increased in passion. He was running his hands up and down my back, from my ass to my shoulders. I pulled him closer and felt his hard cock through his pants as I grinded my body against his. My nipples were hard, along with my big clit. I could feel the back of my panties getting a little damp as well.

I broke our kiss long enough to stare hungrily into his eyes. He looked at me the same way.

"Take me to your room, Daddy" I said in my sultry voice.

"Come along, Little Girl."

Leading me by the hand, I followed him into his bedroom. It was dark and cool, in contrast to the other bright and lively rooms. The walls were a bluish-grey, with the ceiling painted a few shades lighter of the same color. The windows were covered with gunmetal grey blackout curtains, which let no light in at all.

The bed was a giant rice plantation style four poster. The large dresser matched the bed, as did the nightstands on each side. A small lamp on top of each shed enough light to get around. A ceiling fan spun slowly above.

He turned one of the lamps off, which gave the room a more romantic feeling. We kissed again as we stood next to the bed before I let him go and gave his chest a little push.

"Sit down, Daddy. Let me undress you."

He did as I asked.

Kneeling on the floor, I pulled off his shoes but left his socks on (I don't love seeing guys feet). I slowly moved up his legs, reaching his belt. I unbuckled it, and then unzipped his pants. He sat up enough for me to pull them down. I left his underwear on for now.

I unbuttoned his dress shirt as he sat up straight. Taking it off revealed a white wifebeater underneath. I pulled it up and over his head as well.

I couldn't help but stop and admire the sight in front of me. He was in very good shape, muscular, but not overly so. Smooth for the most part, he had sparse chest hair. I didn't see any hair around his navel. His nipples were normal sized for a guy and were standing erect. I gently pinched each one, eliciting a little mmm' from him. I leaned in and sucked on each one for a few moments. This earned me another mmm'.

I ran my hands over the rest of his chest, enjoying the feeling. His skin was smooth but not soft like mine. I could feel the taut muscles underneath. They were firm and solid. I leaned in for another kiss.

As we kissed, my hands traveled down to his navel, then to the waistband of his boxers. I slid my hand a little farther down and felt his erect cock. I found the opening in the boxers and stuck my hand in. Circling his cock with my fingers, I stroked him for a few moments before pulling my hand out.

"Anything wrong, Little Girl?" He was curious why I stopped suddenly.

"Daddy?"

"Yes dear?"

"Would you, um, teach me something?"

"Of course, dear. What do you want to learn?"

"I, um, want to learn how to suck dick, how to give a good blowjob. I've never done it before but want to be good at it."

"Of course I'll teach you. But first, I want to see your beautiful body. I want you to strip for me."

"You mean like dance and take off my clothes?" I said with a giggle.

"Yes, exactly. Show my how that hot little body of yours moves."

I remembered seeing women dance and strip in movies and on TV, so I did my best to imitate what I remembered. I started dancing slowly, rolling my hips and ass, while starting to lift me top off, only showing an inch or two at a time. At one point, I bent over with my ass facing him. As gracefully as I could while almost drunk, I undid my sandals and took them off. Turning back around, I danced some more, pulling my top higher until it was all the way off.

He was watching me intently, obviously enjoying the show. His cock was hard and sticking out of his boxers. He slowly stroked it as I stripped. Giving me a nod of approval, I continued.

I rubbed and tweaked my nipples before moving my hands lower, along the sides of my hips. When I reached the side of the skirt with the button and zipper, I slowly played with them before undoing each. When the zipper was down, I shimmied out of the skirt and stepped out, as it fell down around my ankles.

I was wearing only a pair of purple cotton panties, which matched my purple top. My clit was hard and straining to poke out the top. I reached down and gave it a little stroke before standing up on my toes and twirling around slowly.

Giving me another approving smile he said `come here' with his fingers. I danced slowly over to him.

He gave me a slow head to toe once-over before speaking.

"Take off my boxers, Little Girl."

"Yes, Daddy."

I knelt down and slowly pulled them down his legs. His cock sprang up and free once past the front slit. Staying focused, I continued down until I reached his feet. Lifting one foot at a time, I removed the boxers and threw them in the corner.

"Very good. Now come up on the bed with me" he said as he patted the spot beside him. I held out my hand and he pulled me up.

Sitting up against the head board, he spread his legs.

"Get on your hands and knees between my legs here." He pointed where he wanted me.

"You're going to start by using your hands, as you did before."

I started stroking his dick like when I gave him a handjob. But after a few strokes, he pulled my hands away.

"Now, I want you to get down and lick it. Start with the head then move down the shaft."

I began to lick it like a lollipop, alternation between the head and the shaft. After a minute of this, it was time to suck.

"I want you to take it in your mouth and start sucking. You'll figure out what to do. Just imagine someone doing it to you. It'll make sense. Just go slow and be careful with your teeth. I don't want fang marks on my dick" he said playfully, which made me giggle.

I was very careful when I began to suck, keeping the sharp tips of my longer-than-normal canines off his sensitive skin. I found a rhythm and began to suck in earnest, taking his dick a little deeper down my throat each time. Then it a spot and I gagged. I pulled all the way off to catch my breath.

"S-sorry, Daddy."

"No worries. You're doing good. Don't try to take it so far down your throat. You had a good rhythm going until you tried to go deeper. Find that spot just before you gagged and don't go past it."

"Okay."

I slid my mouth back over his dick and started sucking. I quickly found the sweet spot and concentrated on staying there.

As I sucked, he ran his hands through my hair.

"Oh yeah, Little Girl, that's it. Just like that. You're a talented little cocksucker, aren't you. That's my good girl."

I looked up into his eyes as I sucked. "Mmmm" I hummed.

I alternated between sucking up and down on the shaft to giving the head attention with my tongue. Based on the pleased look on his face, I thought I was doing everything right.

"Little Girl, keep doing what you're doing. You're getting me close. You'll know I'm about to cum when you feel me tense up. When I do, take me as far down as you can without gagging. I'm gonna give you a nice warm, creamy reward. I want you to swallow it all down like you said you would, okay?"

"Mmm Mmm" I hummed.

I sped up the pace a bit, concentrating on hitting the sensitive spots with the tip of my tongue while sucking up and down the shaft. Just like he said, I felt him start to tense up.

"Ohhh...I'm close...about to cum...ahhhh!!!"

I swallowed his dick down as far as I could without gagging as soon as I felt him start to cum. I felt several hot spurts hit the back of my throat, filling it up quickly. I swallowed it as fast as I could, being careful to not spill a drop. After about five or six spurts, no more came out. I still felt him have little tremors, but they got less intense as each one passed. Finally he lay still, breathing heavily. I gave the head one more suck, running the tip of my tongue in his urethra to get any remaining cum out.

"My god, Little Girl. You were born an expert cocksucker! That was incredible for your first time!" he said as he ran his fingers through my hair.

"Mmm. Thanks, Daddy. Maybe I inherited it from my mother. I heard she really likes to suck dick!" We both laughed.

"Seriously though, you did very well. That was excellent for your first time. You swallowed it all like a good girl. I'm very pleased." He stroked my hair as he looked down at me.

"Oh, thank you Daddy! I'm glad I did it right for you. It felt so good when you came down my throat. I told you I'd swallow it all! And it tastes sooo good! Kinda salty but kinda not. The best part was how hot and thick it felt when I swallowed it. I love it! Thank you so much for teaching me!"

"You're a natural, dear. I don't think I had to teach you anything" he said with a chuckle.

I crawled up from between his legs and snuggled against his chest. He pulled me close and stroked my hair.

"Now we need to rest a bit so I can recharge. I mean unless you want to go home—"

"No, Daddy. I want to stay! Can I please? I can go home later." I gave him my doe eyes.

"Of course you can stay. I was hoping you would."

"And I was hoping you'd want me to."

"It's time for a drink. I'll get us some water, then we can have more wine. How does that sound?"

"Wonderful! Let me go get water for us."

"Okay. I'll go to the bathroom and then get the wine."

I crawled up on his chest for a kiss before hopping of the bed and heading for the kitchen.

After we both used the bathroom and drank a big glass of water, Bernie refilled our wine glasses. We sat naked on the couch in the living room and talked.

"Daddy, who was the youngest little girl you've been with?"

"Hmm. When I was 22, I slept with a 14 year old. No one had any idea she was so young. She really did look 18 or 19."

"Cool. I ate my friend's pussy when we were both 13. It was fun!" I replied.

"I bet 13 year old pussy tasted good."

"It sure did. So, how many girly boys like me have you been with?" I didn't expect him to say any. He surprised me.

"Five or six, if I remember correctly" he said smugly.

"REALLY?!? Where? When? Tell me, tell me!"

"I visited a military base in Thailand several times when I was Navy officer. They call them `ladyboys' there because they really do look like young ladies. Some guys got freaked out when they found out they had dicks and didn't have pussies. I just saw them as the hot little girls they were. Like you!" he reached over and pinched a nipple, making me squeak.

"I also met a couple in Europe. One was Italian. You remind me of her a little bit. But she was older, in her 20s."

"I'm so glad that you like the way girls like me are. I know a lot of people won't as I get older."

"You are a beautiful young lady, regardless of what you have or don't have between your legs. Speaking of which, how do you see yourself? I mean truly. What do you want to be?"

"What do you mean?"

"Well, some girls like you feel like they were born into the wrong bodies. They see themselves as girls trapped in boy's bodies."

"Oh. No, I don't feel like that at all. I feel like I'm both. I like my boy body, but I love to dress and look like a girl. My sister asked me if I wanted tits. I said no. I love pussies, but I don't wanna trade my big clit for anything!" I exclaimed as I gave myself a big squeeze.

"Good. See? That's what I was talking about earlier. You're comfortable with yourself. So many people aren't. I hope you never change how you feel about this."

"I know there are a lot of people who don't love themselves. I feel so sad for them. I don't understand. I don't love everything about my life, but I do love me."

"Unfortunately that's true. I think a lot of people aren't taught that it's okay to love themselves. Most people think they should be or try to be something other than what they are. But there are those of us who are comfortable in our own skins and love ourselves" he said as he ruffled my hair. "We're almost a rarity. But you know what? We're usually the happiest people you'll meet. Like you, like me, maybe your stepdad, or your friend Jan."

"Hmm. I think you're right."

We lay there for a little while, not talking much, just enjoying the touch of each other's bodies. I had my hand in his lap, unconsciously stroking his soft cock. After a little while, I felt it start to stiffen.

This got me thinking about what had been on my mind for a few days, something that I wasn't sure I should ask about. Tonight was already an important first experience. Maybe I was being greedy by wanting more. But I felt the urge, the desire for it earlier when I felt the damp spot in the back of my panties. I wanted to give my virginity and have my ass fucked for the first time by a man. I was afraid to ask though.

Bernie noticed that I got quiet all of a sudden, and that I looked to be thinking about something important. He reached over and moved a few strands of hair out of my face.

"Hey, you okay? You got quiet on me all of a sudden."

"Oh, sorry. I'm okay. I'm just, um..."

"Come on, Little Girl. Tell Daddy what's on your mind." He tried to get a laugh out of me but I was pretty serious for the moment.

"Bernie, can I ask you something?"

He set his glass down.

"Yes, Paulina. Ask me anything you want" he said sincerely. I knew it would be okay to ask.

I took a big swallow of my wine, emptying the glass. I held it out for a refill before speaking. He refilled both glasses and sat back, waiting for me to say what was on my mind.

"I, um..." I took a breath and gathered my courage. I drew a little circle on his leg with a fingertip. Looking him in the eyes, I asked my question.

"I want to do something but I'm afraid you won't want me to. But I hope you will." I sucked my lower lip like my friend Carolina did when she was nervous.

"What is it? You can ask me anything. The worst I'll say is no."

"I know. Um, I want to give you something. Something special."

"Okay. That's very sweet of you. What is it?"

"It's, um..."

I felt his hand take mine. He looked me in the eyes and spoke.

"Paulina, it's okay, whatever it is. Don't be afraid to ask. Say whatever's on your mind, okay?"

"Okay." I took another deep breath before speaking.

"I want to give you...my virginity. I want you to be my first. I want you to make love with me. I want your cock to be the first one inside of me. I want...you." I tried to hold in the tears of uncertainty.

He was surprised at my request. Sitting back, he stroked his beard as he watched me. After taking a long sip of wine, he leaned in closer and put his hand on my thigh.

"That's a big thing, Paulina, and I'm truly honored. Do you really want me? I don't want you to say yes because we've both been messing around and drinking. So you need to tell me if this is what you truly want right now."

Looking back into his eyes, I answered him.

"Yes. I really want you. I've been thinking about it for a while. I want my first time to be with someone who I trust, who I know really cares for me. I know you do. I trust you completely. And I know you won't be freaked out after, or have issues with my age. You've already shown me that we feel the same way about it. I can't think of anyone else I'd rather have inside me the first time."

He looked at me for a few more moments before smiling.

"Paulina, it would be an honor to receive your virginity. I'd love to be the first man to be inside you. I do care for you a lot, and have to say that I've thought about this since the first time we were together. I've also worried that one day you would do it but it wouldn't be the best experience. Your first time is special, and should be unforgettable, for all the right reasons." He reached out and palmed my cheek.

The tears of relief and happiness flowed. I looked at him with loving eyes as I pulled him close.

"I'm so glad. I was afraid you wouldn't want to, that it would be too much. I know I can be too much sometimes—"

"Shhh. You're not too much. Not for me. You're just fine. You say what you want, and I love that about you. Most people don't."

"O-okay. Thanks. That means a lot to me." I gave him a little smile.

He let me go and studied me again as he stroked his beard.

"So, young lady, who is it I will be making love with? Will Daddy be loving his sexy Little Girl? Or will I be feeling the warmth of Paulina's exquisite ass? I'm most curious to find out."

I reached my arms up around his neck and pulled him close.

"Both of us. All of us. Every part of me. And you. Us." I drew him into another passionate kiss.

Breaking from our kiss, we looked at each other for a few moments before speaking.

"Okay, Paulina. To do this right requires some preparation."

"I think I know. I...I have a toy I fuck myself with. It's almost as big as you are. I'll be back in a minute."

I grabbed the tube of KY out of my purse before going in the bathroom and sitting on the toilet. I pushed with all my might, trying to pass whatever might be in my colon, but nothing came out. I wiped anyway. Squeezing a large dollop of gel on my fingers, I began to push inside my ass. First one, then two, then a third. It felt like I had enough lube in there, so I went to the bed, where Bernie was waiting for me.

"So, how do you usually do it when you're playing with your toy? I mean, what position feels best?"

"I usually lay on my back, with my legs spread open. That's really the only way I've done it" I said with a blush.

"Hmm. That might be good later, but for your first time, I think I should have you from behind. That way we can prop you up on a pillow if you want."

"That sounds good. Just show me how you want me."

"Let's get a refill before we do this." He got the wine bottle and poured us each a glass. Raising them high, he made a toast. "Here's to you, Paulina, for sharing yourself with me. It's a great honor, and I feel very lucky. Salute!" We clinked the glasses together before we each had a long swallow.

"I want to you to get on your hands and knees, in the center of the bed, with your ass up high."

I took the position he wanted me in.

"Now, lay your head and arms on the pillow." He slipped a pillow under my arms.

He got on the bed behind me. With his hands gripping my hips, he pulled me close. I felt his hard cock poking my cheeks.

"Are you comfortable? If not, we can move the pillow."

"This is fine."

"Okay. Your ass is lubed up and my dick is nice and slippery. We're gonna go slow. Say something and stop me if it hurts or doesn't feel good."

"I will. I love feeling my toy, so I think I'll be alright."

I felt the tip of his hard cock against my sphincter. I relaxed it as I pushed back on it. He pushed forward at the same time.

"Unnnhhh" I let out when the head of his dick entered my ass. Holding still, I let myself get used to his big dick before moving. Slowly, I started to move my hips back and forth, pulling a little more of him in each time. The pain soon gave way to pleasure as my ass accommodated him. He began to pull my hips to him as I pushed less. After a few moments, he was in control and setting the pace.

"Ummm...ohhh...Daddy, that feels so good! Fuck me harder!"

"You're little ass is so tight! I'm gonna split it open, Little Girl!" he pulled my hips back harder.

He fucked me hard, going all the way in deep with each stroke. It felt like he was hitting my stomach from the inside.

Once I was used to his size, I felt no pain, just extreme pleasure. After a few slow strokes, he was inside me to the hilt. I felt his big balls against my little ones, as his pubic hair tickled my cheeks.

"Ohhhhhh...mmmmm" I sighed in pleasure. Without moving backwards or forwards, I clenched his cock and swiveled my hips in a circle.

"Oh, Little Girl...that feels so good!" he almost moaned.

I looked back over my shoulder and blew him a kiss.

As soon as I started moving gyrating my hips, it felt as if a switch was turned on inside me. A wave of pleasure rolled through my body, letting me know what I wanted. My pent up desire was letting itself out. I felt like Liz Taylor in Cat on a Hot Tin Roof.

"Daddy, fuck me. Fuck me hard. As deep as you can go. I want it so bad..." My voice was low, almost a growl.

"Yes, Little Girl. I'm gonna fuck your little ass hard till you scream!"

Gripping my hips harder, he pulled me all the way back on his cock, and then started thrusting with fast, hard strokes.

"Ohh...uhhh...uhhh...ahhh..." I was loud and sounded just like a woman getting fucked. I didn't hold back.

"Ohh...ohh...ah...Da-...Daddy...fuck me harder..." I begged in my little girl voice.

"Yes, take it, my Little Girl...take all of me!" Letting go of one hip, he grabbed a handful of my hair and pulled it to him with each thrust.

"Ahhhh!!! Unnnhhh..." My insides felt like they were on fire with pleasure. I realized that my toy would never make me feel this good.

Then I felt it. My first orgasm was imminent. It quickly started to build. It was an electric heat inside that I couldn't explain. I had never felt something so intense before. I didn't know it at the time, but his dick was hitting my prostate with every thrust. I've heard that it feels similar to a woman's G-spot.

"Oh...unh...unh...OH OH AH AH AIYEEEEE AHHHHHH!!! I'M CUMMING!!!"

My ass clinched his dick harder than before as I felt my mind and body explode. My legs wobbled as several spurts of cum shot out of my big clit.

"YEAH Little Girl! Cum for Daddy!" he cried as he felt my ass clamp down on him like a vice.

After a moment, I began to relax my grip, while his thrusts slowed down. I felt like I couldn't catch my breath yet.

"Da...Daddy...d-did you...did you cum?" I panted.

"Oh, no, Little Girl. I'm not done fucking you yet."

Suddenly, he pulled his cock all the way out. The empty feeling made me whimper with disappointment.

"Unhhh...Daddy? No! Put it back in..." I pleaded.

"I will, Little Girl, but now you're gonna turn over and get on your back. I'm gonna fuck you like a real woman. Would you like that?"

"Oh yes! Please!" I was ready to go again.

He smacked me on the ass before I turned over.

I threw the pillow on the floor as I lay back and spread my legs.

"That's right, spread those legs! Let me see that big sexy clit. I'm gonna fuck your ass like a tight, young pussy. You want that, Little Girl?" he growled.

"Yes Daddy! Fuck my little virgin pussy! Take my cherry! Make me a real ladyboy!"

He teased my hole a few times, rubbing his cock head over it but not pushing it in.

"Please Daddy, please! Stick it in!" I begged.

Giving me a sly smile, he thrust it in hard all the way in, balls deep.

"OHHHH! Unhhh...yes...fuck me!"

"Give me those ankles!" he commanded as he roughly grabbed them and put them over his shoulders. "You keep them there while I fuck you!"

"Ohhh...yes Daddy!"

He grabbed my hips and started thrusting hard and deep. He looked like he found his stride and wasn't cumming anytime soon.

"Your little pussy feels so good and tight. I love fucking little virgin girls! I'm gonna want to fuck you all the time!" he said in-between thrusts.

"You can fuck me whenever you want, Daddy! My little pussy is yours whenever you want it! Ohhh..."

After a few more thrusts, he pulled my ankles from around my neck.

"Now, Little Girl, you pull those legs back and spread that little pussy as wide open as you can" he ordered.

I felt my hamstrings stretch and burn as I pulled my ankles back, spreading my legs as wide as possible.

"Oh yes, that's good." He got back in his stride, going deep with each thrust.

"Clinch that little pussy hard. Make me feel it!"

"Yes Daddy!" I clenched my ass as hard as I could.

"Oh yeah, you hold that tight"

"Unhhh...unhh..." It was difficult to keep a tight grip on his cock. My muscles burned and quivered.

"Yes...yes...I'm...I'm gonna cum! AAAAHHHAAA!!!"

With a thrust that was harder and deeper than any before, he held it balls deep. He shook and shuddered, letting out another cry of pleasure. I felt a warm wave of liquid fill my rectum. It was hot, like scalded cream. It felt incredible.

"Take my babies, Little Girl! I'm gonna get that little pussy pregnant!"

His climax pushed me over the edge. Hearing this, I came again. My clit and balls pulsed again, spurting a few times, though not as much cum came out. The feeling was just as intense though.

He started thrusting again, but with less power on each stroke. I watched his chest, glistening with sweat, as is heavy breathing started to subside. I could feel his cock soften slightly.

Finally, he stopped moving, with his cock still deep in my ass. He leaned in on me, resting all his weight on my chest. It was an unexpected feeling. The pressure felt good. Staring into each other's eyes, we kissed passionately. I was sure his tongue went into my throat. After our kiss, we lay there panting, catching our breath.

"Daddy?" I asked in a sultry voice.

"Yes, Little Girl?"

"I wanna suck your dick clean. I wanna taste your cum and my honey from my little ass on your cock. Feed it to me, Daddy."

"You're a dirty Little Girl, aren't you. Yes, you're gonna suck my dick clean. Now get down there and open that mouth."

I hopped off the bed and got on my knees, careful to keep my ass clinched tight. I didn't want any of his cum to drip out. He scooted to the edge of the bed and spread his legs.

I stroked his semi-soft as I looked at it closely. Its scent was a combination of us. I saw a big drop of cum about to ooze out of his urethra, so I took him in my mouth before it dripped out. Sucking gently, I used the tip of my tongue to lick and clean the head. As I licked, I felt several little pulses of his muscles as the last drops of his cum coated my tongue. I sucked and licked his softening shaft and head until I couldn't taste either of us anymore. I looked up into his eyes and licked all the way around my lips, like a fat kid that just ate a delicious dessert.

"Mmm, Daddy. We taste so good!"

"Come up here, I want a taste too." He pulled me up and kissed me deeply.

"You're right. We do taste good. The flavor of pleasure!"

He lay back on the bed, making room for me. I snuggled up to his side. He put an arm around my shoulders and pulled me close.

"So, Little Girl, how do you feel?"

"Oh my god, I never imagined that would feel so good! I feel like my body is buzzing and my insides are still hot. That was incredible, Daddy."

"I'm so glad you enjoyed it. It felt incredible for me, too."

"I'm never gonna forget this. Nothing or no one will ever compare to it. Never."

"Good. I always want you to remember me as the best, as well as your first. He gently rubbed one of my nipples, earning him an `mmm'.

We lay there for a little while longer, until our breathing and heartbeats were back to normal. I knew we had to get up, but I didn't want too.

"I'm thirsty. You want something too?" he asked.

"Yes. Wine, please."

"Okay, but have a glass of water first."

He got up and headed to the kitchen. Stopping in the bathroom, I heard him pee. It was a strong, loud stream. I wanted to hold it for him and maybe taste it, but I was too worn out to get up. I felt like I was made of jelly.

A few minutes later he returned with two big glasses of iced water, as well as the wine bottle. We gulped the cold water down slowly, not wanting to get brain freeze. He refilled our wine after setting the empty water glasses down. I didn't realize that it was the second bottle of the evening, and that it was half empty already.

Lifting his glass high, he toasted me.

"Here's you, Paulina, my Little Girl. It was a pleasure and an honor to be your first and receive your virginity. I will remember it fondly, always."

"And here's to you, Bernie, my Daddy. Thank you for making my first time such an incredible experience. I never imagined it would be like that. I'm so glad it was you. I knew I wanted it to be you the night we spent time together, even before we kissed and played. Thank you so much! And I meant it when I said you can fuck me anytime you want. My little ass will always be yours."

"Salute!" We clinked our glasses and had a big sip.

"Well, Paulina, it's 9:30. I should probably get you back home. You have school tomorrow, right?"

"Yes, I do. I wish I could stay the night with you, though" I said with a pout.

"Maybe another time. You'll need to bring some clothes with you. And maybe a toothbrush." He winked with a smile.

"Well then, I will." I smiled back.

My voice sounded less cheerful when I asked my next question.

"Um, when will I see you again?"

He stroked his beard for a moment. "Hmm. I'm not sure, but it will probably be a couple of weeks. I'm going to Argentina and Chile for the next two weeks for work. I may have to go someplace else from there."

"Okay" I pouted with a big frown. "Promise you'll let me know when you get back?" I gave him doe eyes.

"Of course I will. I'll send you some postcards while I'm gone, too."

"Thanks! It'll be cool to see where you went."

"I think it's going to be a good trip."

"So, Daddy," I twirled the ends of my hair and stepped closer. "Will you bring me back another nice present? I love this one." I fingered my bracelet, which stayed on my wrist the whole time.

"Of course I will, Little Girl. I'll bring something very nice back for you."

"Yay! You're the best, Daddy!" I pulled him in for another passionate kiss. He gripped my ass and held me tight.

He released me from our kiss after almost a minute.

"Alright Little Girl, finish your wine and get dressed. I need to take you home."

"Okay." I gave him a faux pout.

I drank the rest of my wine down in one big gulp. I knew I would be tipsy for the next few hours and giggled to myself. After dressing, I went to the bathroom to freshen up.

I had to pee, but knew it was going to be difficult. I had to push my bladder to let the urine out, but I didn't want to push my ass and let any of his cum seep out. After a minute of concentrating, I was able to do it.

I reapplied my lipstick, which was mostly gone from sucking his dick. After brushing out my hair, I looked at myself in the mirror one last time. I needed to make sure that I didn't have that `I just got fucked' look when I got home. I smelled my wrist and was disappointed that my perfume had faded away.

Bernie opened the car door for me and held my hand as I got in. He really was a handsome and distinguished gentleman. I couldn't help but giggle more.

The drive to my house was short, but we did have time to chat.

"Bernie, what's your name short for? I've been wanting to ask but forgot to earlier."

"It's short for Bernard. But everyone's called me Bernie since I was a kid."

"Hmm, Bernard. I like it! Can I call you that instead? I really don't care for nicknames. Plus, I don't want to be like everyone else."

"Of course you can. That's very sweet. No one has asked me that before. And, you know" he ruffled my hair, "You'll never be like everyone else!"

"Goodie! I mean thank you, Bernard." It was hard to remember to sound ladylike while tipsy.

"Thank you, Paulina. I'm glad you like it."

When we were just a few blocks away from my street, Bernard brought up an obvious question.

"Paulina, I can't drop you off in front of your house. I also don't want to drop you at the house where I picked you up. Any suggestions?"

I thought about it. There was a church next to our house. We could go around the other side, but it was still too close. But there was another one three blocks away. I could walk home easily from there.

"Turn on the last street before the canal. There's a church at the end. My house is three blocks away."

"Okay...but are you sure you'll be alright walking around at night like this?"

"No one will bother me, count on it." I flashed him a full wolf smile.

"I see. I hope you don't have to eat anyone, then." We both laughed.

We arrived and he parked. I sat with him for a few minutes before getting out.

"Bernard, thank you again. You made my first time a really special experience. I couldn't have asked for anything better."

"It was my pleasure, dear. You're a special girl and deserved to have the best experience I could give you. You know, I'll always have a piece of you with me now, wherever I go."

"Aww, you are so sweet! But I know you mean it. You...you make me feel special, Bernard. I can't thank you enough."

"Well, Little Girl, you should get home. I'll send you some postcards from South America, and have some new stories for you as well."

"Don't forget a nice present, Daddy" I said with a coy expression while twirling my hair and batting my eyes and giggling. "And promise you'll call when you get back, okay?"

"I will."

We both reached over for one more slow kiss. Before pulling away, I whispered in his ear.

"I love the bracelet, it's beautiful. Thanks for thinking about me."

"Bye!" I hopped out of the car and started to walk home.

He waved as he drove off.

The last glass of wine before leaving Bernard's brought my buzz back. I was so happy that I wanted to skip home, but I didn't want to lose my balance. So I walked slowly, making a little game out of avoiding the puddles. Giggling all the way, I replayed the evening's experiences in my mind. I almost couldn't believe that I wasn't a virgin anymore!

I gathered myself together and tried to suppress my giggling when I reached the walkway to our front door. Being tipsy, I didn't even think of going in through the family room.

I was relieved to see that my mother's car was gone. She must have gone to the grocery or Time Saver, our local convenience store.

After letting a deep breath out, I went inside. The usual group was there. My stepdad, Dawn, Shawn, Joe (or Pervert, as we called him) and Ann. Gayle was sitting in the corner reading.

"Hi y'all" I tried not to giggle.

"Hey kiddo. Where you been? It's almost ten. You have school tomorrow." My stepdad asked with a faux stern face.

"I know. I was at a friend's house. We were talking and stuff, and lost track of time." I gave him pouty lips. I knew he wasn't really upset with me.

"Alright, come home earlier next time, okay?"

"Okay." This time I couldn't hold in the giggles.

He didn't really notice them, but Ann did. So did Dawn. Ann gave me a suspicious look while keeping her smile.

I realized that she heard me, and then I knew I was busted when she gave me that look. I think I blushed a little as I looked down and sucked my lip.

"Um...goodnight y'all." I turned and walk away quickly.

Shawn watched me walk away, then he looked at everyone.

"That was weird. No hugs. What's goin' on with her? She usually won't go without them."

"Don't know, man. Maybe she's got somethin' on her mind" Pervert observed.

"No telling, I guess. I'll ask her tomorrow" my stepdad replied.

Ann heard me go to the bathroom. She was going to find out what was going on, thinking to herself this'll be fun!

"I gotta go pee." She stood up and walked to the bathroom.

I was sitting on the toilet humming to myself as I peed while clinching my ass closed. It was easier than before. Because I was tipsy, I forgot to lock the door.

As I was standing up and flushing, I didn't hear Ann's soft knock on the door. Before I could answer, she came in and locked the door behind her.

We looked at each other for a moment before I blushed and put my hand over my crotch. My skirt and purple panties were on the ground around my ankles. As she had never seen me bare below the waist, she was quite interested. Starting above my belly button, my stomach was smooth and tight, with a hint of muscles showing. Moving down, my pubic mound and thighs were hairless.

Before I could cover up, she got a good look at my big clit. It was smooth and soft, looking like it might be three or four inches long and thin when hard. My balls weren't visible, as they were tucked between my legs. Looking back up at my eyes, she gave me sly look before speaking.

"Interesting. I wondered what you look like under those cute clothes."

"Um, thanks. I bet you're pretty under yours too." I giggled.

"I am. So, what were you drinking, girl?"

"Wha?? I, um..."

"Don't bullshit me. I heard you giggling and saw you concentrating on your balance when you came in. Just like you were the other Saturday night!"

I blushed and looked at my feet. I was definitely busted.

"I, um...we, um...my friend took her mom's bottle of wine. We both drank some" I said with a giggle.

"Uh huh. Just wine?"

"Yep, just wine. That was all!"

"Girl, I'm all for gettin' a buzz whenever, but Marie (my mother) will have a fit if she sees you like this."

I gave her a confident, tipsy face. "I don't give a fuck what she thinks. I'll drink in front of her if I want! She can kiss my ass!"

"Wow, you really do hate her ass. But what would Hank say? I don't think he'll be happy. He might be disappointed. Shawn too. You don't want that, do you?"

"Oh...no. Please don't say anything, okay?" I gave her pouty lips and sad eyes.

Putting her hands on her hips, she gave me a playful smirk.

"Don't try that cutesy shit with me girl, `cause it ain't gonna work!"

"Fine." I gave her a real pout this time.

"Look, I just don't want you getting' in any trouble, okay?"

"I know. Thanks."

"Alright. Now try not to giggle if you come back out there."

Before she turned to leave, I pulled her into a hug, which she returned.

"I guess I owe you one, huh?" I said in her ear.

"Yep, I think you do. And, um, pull your panties up. You're rubbin' your soft little dick on me."

"Oh!" I turned beet red as I reached down to pull up my panties. "Sorry!" I burst into giggles. She smiled and ruffled my hair before walking out.

I ran to my room giggling as soon as she left.

I stripped off my clothes, kicked off my sandals, and jumped onto my bed. I lay on my back, stretching out my arms and legs as much as I could. My head was still swimming from the wine, as well as everything else that happened. It still seemed unreal, but I only needed to feel the lovely gold bracelet on my wrist to know that it wasn't a dream and that everything did happen.My big clit got hard again as I thought about what we did earlier. I smiled as I remembered that I still had some of Bernard with me. My little ass was still full of his cum! I had been holding my muscles tight so that none would seep out. None had so far.

I spread my legs and inserted my middle finger, slowly twirling it inside. It was a little sore but still felt good. I inserted a second finger. Twisting them, I scooped out a big blob of cum. I brought it to my nose and inhaled deeply. The scent was light and musky at the same time. Sucking my fingers into my mouth, I rolled the cum around my tongue. It tasted like it smelled, but it had a touch of saltiness as well. It was delicious. I swallowed it down like a spoonful of heavy cream.

I remembered that I told Jan I would call her when I got home. Before dialing her number, I stuck my fingers in my ass again to pull out some more cum. I rubbed it over my lips until they were totally coated. I giggled knowing that I would smell and taste him while we talked.

"Hello?"

"Heyyy Jan! Guess who?" I giggled.

"Hmm, let me think. Happy, giggly – I know! Paulina!"

"Yessss! It's me!" I couldn't hold in the giggles and laughter.

"Girl, if I didn't know better, I'd think you're tips from drinking, with all that giggling going on. Hmmm?"

"Uhh, um, maybe?"

"Paulina! It's Thursday night. Don't you have to go to school tomorrow?"

"Yeah, but I don't have school tonight!" More laughing.

"You're goofy. So tell me, how'd your date with your Daddy go?" This time she laughed.

"My date with Bernard was excellent. We had a wonderful evening." I tried to use my best imperial voice as long as I could, but succumbed to the giggles again.

"Bernard?"

"Yes, Bernard. It sounds so much better than Bernie. Much more fitting for a distinguished gentleman like him."

"Wait, I thought he's a handsome and distinguished gentleman!"

"Oh yeah. He sure is!" We both laughed some more.

"So, details? Tell me all about it!"

We talked for a bit. I told her about his house, how he cooked authentic Italian food, and about his garden.

"Guess what?" I giggled.

"I have no idea. Tell me."

"Daddy gave me a really nice present."

"Did he? You said he would. What is it?"

"It's a 14 karat gold bangle bracelet. There are seven peridots set in it, with four little diamonds on each side. You know, the peridot is my birthstone. Anyway, it's real old, and it's from Italy. He said he thought of me as soon as he saw it. I love it!"

"Wow!" She was almost speechless. "He did say he'd get you something gold, but I didn't expect that. I mean, diamonds? And gems too? That must have been one helluva handjob you gave him last Saturday!"

"No. It, um, it wasn't for that" I said in a serious, thoughtful tone. "He said he had such a good time meeting and getting to know me, that he would have thought of me and got it anyway, even if we didn't do what we did. I remember exactly what he said:

"You're genuine and comfortable being yourself. You truly mean everything you say, and you say it with conviction. Especially when it has to do with others."

"I told him that I truly cared for people. He said "That, my dear, is one of the best qualities anyone could ever have. Truly."

"Jan, I almost cried because he complimented me. He wasn't just telling my how beautiful and sexy I looked. It was about me, not how I looked. I-I told him that it really meant a lot. I don't usually hear things like that about me. Usually it's about how pretty I am, or how smart."

I got teary eyed talking about it.

"I-I'm sorry." I wiped my misty eyes and blew my nose in a tissue. "It just...I don't know how to say it. He made me feel real good inside. Know what I mean?"

Jan was having her own struggle to not tear up as she listened. She was happy for me. She was afraid that our little date was going to just be him accommodating me since he said he would, only to write me off after. The fact that he was genuinely sweet and kind and attentive to me was a surprise. And very romantic. I guess he really is a handsome, distinguished gentlemanlike she says, she thought to herself.

"Paulina, that's so sweet and romantic! I'm so glad you had such a good time. He sounds wonderful. Maybe I can send Jeff to him for lessons!" We both laughed.

"Now, the juicy details. What else did y'all do?"

"Well, evidently I'm a `born natural' when it comes to sucking dick!" I wasn't going to tell her I gave him my virginity. Not yet.

"Right on, girl!"

"I asked him to teach me how to do it, but after a few minutes he said there was nothing to teach. I was an expert already. He did tell me one thing that really did make it easier."

"What?"

"Since I have my own down there, he said to imagine someone doing it to me. I did, and it felt natural from the point on."

"Hmm. I couldn't have given you that advice."

"I did have one little, um, hiccup though."

"Yeah? What was that? I've had plenty."

"I tried to swallow him down too far and gagged."

"Don't worry about that, sweetie. I've gagged so many times that I can't remember. I think I even puked on a couple guys. It was their fault, though, trying to stuff their dicks as far down my throat as they could."

"I would have been so embarrassed if I puked on him!"

"But you didn't."

"No. So we stopped for a minute. I he told me to remember how much I could take before gagging, and to not go further than that. I didn't have any more problems."

"Good. So did you swallow when he came, like you said you would? Or did you chicken out and spit?"

"Please, girl. Of course I'm not going to let a drop of cum from such a handsome, distinguished gentleman be wasted and spit out" I said in my imperial voice.

"Of course you wouldn't" she said, imitating me. We both laughed.

"When he came, it was so much! I had to swallow like five or six times. But it felt so good! He tasted good too."

"Nice. I like swallowing a big, hot load."

"Now that I know what to do, I'm looking forward to going to the office with you!"

"Hey, now you got me worried. I'm not sure I'll be able to compete with a `born natural'!"

"I think you'll do fine. You have prettier, lusher lips than I do. And my lips are luscious!"

"Well..." she said modestly, "they are pretty luscious, aren't they."

"You know what would be funny? What if we pulled Yvonne in there with us!"

"Paulina! She'd die from embarrassment!" We both laughed at the thought of Yvonne on her knees at the glory hole in my stepdad's little office in the garage.

"Yawwwn..." I was tired and couldn't hold it in. "I'm sorry! Didn't mean to yawn on you. I'm just tired."

"I know. You had an exciting evening. Go get some rest and we'll talk soon. Goodnight, sweetie."

"'Night, Jan."

Next: Chapter 2: Paulina Is Heard Masturbating


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