I don't suppose my story is really any different when it comes to cross-dressing. It began when I was young and continued to flourish as I grew older. I lived alone with my mother growing up. My father had been killed in car wreck when I was 8. He had been a successful stockbroker and had left my mother and I financially stable, if not wealthy.
My mother was also a broker and continued to work after my father passed away. She had never remarried. Her work and raising me were her only focus. She dated, but never seriously. Instead we traveled a lot growing up, as my school and her work schedule allowed.
My mother had been raised to think that a woman should always look her best. Her wardrobe was always bursting with the most fashionable clothes and shoes. As I grew up, I constantly heard my mother receive compliments for her style. It always made me feel proud to know that I had such a beautiful mother. I loved to see the new outfits she had selected and I often wondered what it felt like to wear those beautiful clothes.
She worked long hours and after I reached a certain age, she allowed me to stay home in the evenings by myself. Naturally, my curiosity about her clothes eventually led me to her closet. I would touch the soft fabrics of her blouses, skirts and dresses. The silky things I found in her lingerie drawers held my interest as well. She had a wonderful collection of sexy panties, bras, and hosiery. Naturally, it was just a matter of time before I began to try them on. I would go in her room nearly every day when I got home from school to try her sexy clothes on. I lived for the moments when I could slip in some of her silky underthings and put on a pair of her sexy high heels.
I had always been pretty small for a guy. By the time I finished high school, I was a whopping 5'2" and weighed about 120 pounds. By contrast, my mother was about two inches taller than me even without her heels. This turned out to be a great thing since she and I were virtually the same size. I was able to wear all of her clothes as well as her vast high heel and boot collection.
Being the fashion conscious woman she was, Mom frequently would set out older clothes and shoes for donation to local charities. I soon learned to divert those boxes to my room for inspection before they went to the donation box. A blouse here, a skirt there and I soon had a fairly respectable collection all of my own. I had a door in my closet that lead directly into the attic of our house where I could keep my treasures.
After I had my own transportation, I began going to the local mall and buying my own things. The thrill of doing it the first time was something I'll never forget. I had walked into a lingerie store and began looking through the panties. A cute young sales girl had walked up and asked if I needed help. At first I was embarrassed, but she did her best to put me at ease. Naturally, I used the time tested "buying something for my girlfriend" excuse. She smiled and winked. I was certain she knew what I was doing! After 20 minutes of shopping, I had my hands full with 5 matching bras and panties. I had also purchased a lacy black garter belt. She even helped me select some stockings to go with it.
Last summer I graduated from high school. My Mom had been offered a temporary position with her brokerage in Japan for the summer. We had debated whether I would go with her or not. I had already secured a summer job I was looking forward to, but the opportunity to live somewhere different for an entire summer was appealing. Ultimately, I decided that I would stay home and work my summer job. Mom was disappointed, but she said that it would be a great opportunity to practice living on my own before I left for college. I agreed.
I also knew it would be a wonderful opportunity for spending extended time as Karlie, which was what I had begun to refer to myself as when dressed.
The week Mom left was a mix of emotions. I was sad that she would be gone for two months, but the thought of having the house all to myself filled me with excitement. After I dropped her off at the airport, I quickly sped back home to enjoy my time alone.
I spent every night that summer dressed fully as Karlie. I began to experiment with Mom's make-up. I had always had somewhat feminine features and very little facial hair. A close shave and a little makeup really helped. After much trial and error, along with repeated how-to videos from You Tube, I got to the point I could get made up and not look like a total hooker. Each night I would pick out an outfit and dress. I would spend time walking in front of the large mirror my mother had in her bedroom. I wanted to make sure I moved like a sexy young lady and not a clumsy 18 year old boy.
I also began to search out other crossdressers online. I met many nice gurls from across the country, and even around the world. Those chat sessions helped me realize that I was not alone. I also picked up a lot of valuable tips for being a gurl. I enjoyed the thrill of exchanging photos with them and the many compliments I received.
One night in mid-June, I was dressed in a short black skirt and chemise with silky tan pantyhose. I was looking through my mother's huge closet for a favorite pair of heels of mine. After finally realizing she must have taken them with her, I turned in frustration to walk out. I spotted a cardboard box in the corner I hadn't noticed before. Mom had been rearranging things in her closet and had moved a few things to the attic the week before she left for Japan. I remembered that she had declined my help, which had seemed odd to me at the time.
Out of curiosity, I reached down to pick the box up. It was actually quite heavy. Without hesitation, I pulled the flaps open and was more than a little surprised to see what was inside. The box contained dildos and sex toys of all shapes and sizes. I had seen my mother's vibrator in her bedside table before, so the toys were not that shocking. However, the numerous porn DVDs as well as a large number of unmarked DVDs in a separated binder were. It definitely got me curious. I grabbed the whole box and walked out in to my mother's bedroom. I removed the DVD binder and began to flip through them. I couldn't find labels on any of them, so I just picked one and placed it the DVD player. I grabbed the remote and walked to sit on her bed.
When the DVD started, I watched on the large screen plasma TV my Mom and Dad's honeymoon trip to France. Mom looked so young and beautiful. Dad was really handsome as well. The video continued for approximately 30 minutes showing them as they went to the Eiffel Tower, the Louvre, and many other places in Paris. It made me feel sad to see Mom and Dad look so happy since he was now gone. He was constantly making jokes as they walked around. It was funny to hear my Mom laugh. I hadn't heard her laugh like that in a long time.
There was a break in the video. I picked up the remote and fast forwarded through the black areas. When the video restarted, the camera was obviously on a tri-pod in a luxurious hotel room. I felt a touch of embarrassment. The camera was pointed at the bed!
I saw Dad walk from behind the camera. He was naked. Feeling ashamed, I reached for the remote to stop the video, but I heard him talking softly to Mom. She slowly appeared from the left side of the screen. She was dressed in sexy black lingerie complete with stockings and heels. She looked unbelievable. Her thin shape was accentuated by her firm breasts and ass. Wow, I thought to myself. She was really something!
After a little urging from Dad, she stopped in front of the camera and did a little twirl. I marveled at how sexy she looked. I also noticed that my father was pretty impressive as well. He was in great shape with a nice chest and flat abs. I hadn't got my slender body shape from him, for sure. He turned a little towards the camera. I was amazed by his penis. It was huge! Even limp he was much bigger than me.
I watched the video further as he took her into his arms and they began to slowly kiss and caress one another. His hands roamed all over her sexy body. I was a little ashamed that I kept watching, but I just couldn't make myself turn it off.
I watched with my mouth agape as my mother kissed her way down his chest and abdomen until she was kneeling in front of him. Her small little hand grasped his hardening cock before she slowly took it in her mouth. My mouth suddenly felt dry as I watched her begin to suck him. I could feel my own little cock getting hard in my pantyhose.
I was shaken from the erotic sight by my iPhone vibrating inside my bra. I reached to get it and saw that it was Mom calling. I quickly grabbed the remote to mute the volume before answering.
"Hi, Mom!"
"Hi Honey, how are you," she asked.
"I'm fine, How about you?"
"Great, just busy! I was leaving to catch the train to the office and I thought I'd call and see how you were." I could sense a little exasperation in her voice.
"Oh, okay. I'm fine."
We talked for a couple more minutes. I realized I was distracted by the images on the TV and my part of the conversation consisted mostly of yeah and okay.
"Honey, what's wrong," Mom asked.
"Nothing, why?"
"You just seem preoccupied."
"Sorry. I'm just watching TV," I lied.
"Oh, what are you watching?"
"It's just an old movie."
"What's it about?"
"It's a love story set in Paris. I don't know the name of it." I smiled to myself for my little joke.
"Okay. I see."
We talked for a little while longer. The whole time I was watching her suck my late father's big hard cock. I wondered what it would be like to be knelt in front of a handsome man like him, doing that. Finally, she said she had to go and she would call me the next day. I felt a bit guilty, but the visions I was seeing on the TV were too exciting! I said goodbye and returned my full attention to the sexy display.
I had scooted back on the bed and was resting against the headboard on Mom's big soft pillows. I was so turned on watching the two of them. Dad had focused the camera in to get a close up of mom at work. My God, he had to be over 7" and was extremely thick.
I looked through the box of toys and I found a very realistic looking fake cock. It looked to be about the same size as dad. I felt it in my hands and imagined what it would feel like if it was real. I watched Mom continue to slide her mouth up and down that huge thing. She was trying to get as much down her throat as she could. She wasn't able to get all of it, but she was certainly doing her best.
I kept playing with the fake cock and I decided I wanted to see how it felt. I brought it to my face and opened my mouth. I felt like I almost had to unhinge my jaw to get it inside! I slowly slid it in my mouth. I didn't really like the plastic taste but God it made me feel dirty to be sucking on it. I slowly worked about half of it in my throat before I felt I was gagging. I wasn't nearly as good as Mom!!
I kept practicing as I watched Dad reach down to pull Mom to her feet. They kissed passionately before he led her to the bed. He gently nudged her until she was kneeling on the edge. When she was in place, he knelt behind her and slowly pulled her silky black panties down over her garter belt to her knees. His face was quickly planted on her sex.
I watched with keen interest as he slowly licked her up and down. She was moaning and talking as he did so. It was obvious he was licking her pussy, but I could see that he was also licking her ass. It made me wonder if mom enjoyed anal sex as well. I had experimented with my finger a few times. Now that I knew about this collection of toys, I knew I would have to try more!
I was still sucking that fake cock as I watched Dad stand up and slowly slide his hard cock into her from behind. She moaned softly as he entered her. My hand had found its way under my skirt and I was lightly touching my little clitty through my pantyhose. It was so hard.
On the TV, Dad began to slowly fuck Mom with his big cock. She moaned and purred. I watched as she reached one of her hands down between her legs. I assumed she was touching herself. Dad kept telling her how sexy she was and how much he loved her.
It was such a sexy sight watching them. They were so young and in love. Mom was absolutely breathtaking, while Dad looked like he had been chiseled from stone. I turned to look at Mom's beside table where she still had a picture of him. He had been really handsome.
I noticed additional movement on the TV screen and I turned back. They had changed positions. Mom was now on her back and Dad was between her spread thighs. Her sexy, stocking covered legs were sliding up and down his ass and legs. I turned up the volume so I could hear their passionate moans clearer. Mom was telling him how good it felt to have him inside her.
Dad gradually increased his pace. My own hand was down inside my pantyhose and I was stroking my little clitty quickly. I knew I was about to make a mess of pantyhose.
Dad told Mom that he was getting close. She just groaned and wrapped her arms around his neck. Dad was really slamming into her. I felt myself getting ready to cum as well. After just a few more strokes, I shot my gurly cum into my pantyhose.
I heard Dad groan and I watched as his strokes got shorter and much more intense. He was filling her up with his cum!! Mom moaned and told him how good it was.
I laid there recovering as I watched Mom and Dad kiss. They looked so beautiful together. I looked down and saw I had made quite a mess. My hose were soaked. I pulled my hand out and began to lick my cum from it. I had only recently started doing that and it was quite a thrill.
I spent the rest of the summer watching their sexy videos together. Apparently, they had quite the active lifestyle before I was born. I had no idea that they had been so wild. Most of the videos had been filmed at their big apartment in the city. We had lived there until I was 5, when we moved out to our house in the suburbs. I watched them do everything imaginable. I saw Dad make love to other women and Mom with other men. I saw Mom have sex with other women and I even watched my Dad get a blowjob from another man. I thought to myself how lucky that man had been. Dad's cock had looked amazing.
I often imagined myself being Mom when I watched the videos. Watching her fucking and sucking turned me on like nothing I had ever experienced. She always seemed to be dressed in sexy lingerie. I experimented heavily with the fake cocks. I began trying to fuck myself with them. It was difficult at first, and I learned that it took a lot of preparation. I was soon taking the 6" dildo easily. I never was able to get the big one in though. I always seem to get too aroused and lose control before I did. I was amazed that she had been able to take Dad in her ass so easily.
Between work and my nightly play time, the summer passed quickly. I was getting more excited about going to college and being able to continue my private life as Karlie.
Mom came home in time for us to take a quick trip to Paris before I left for school. We spent a lot of time going to museums and seeing the sights. She also spent a lot of time shopping. I acted disinterested, but I was actually envious as she tried on so many sexy outfits. I knew they were my size and I really wanted to try them on as well. I knew that whatever she bought, eventually I would get to!
We came home and it was soon time for me to pack for college. I was a little sad to be leaving home but I knew that it was a necessary step I had to make in life. Mom was really busy with work, so she couldn't accompany me on my trip to my new school. She had promised she would be up the following weekend to make sure I was settled in.
I loaded up my car and I left. It was an 8 hour drive to my new school. I was fortunate in that the university I had chosen was having a housing shortage, and I would not be able to live in the dorms. I would have to suffer the fate of having my own private off-campus apartment! When I arrived I quickly secured my key and began moving into my new home.
Having the summer alone had definitely prepared me for the new freedom I now had. After classes started, I would go home at the end of the day and put on something girly and do my homework. I made a few friends quickly and enjoyed spending time with them, but I really cherished the time I could have as Karlie.
Having my own place and a credit card I was solely responsible for allowed me to purchase things on-line without mom's approval. I acquired breast forms as well as additional clothes and lingerie. Mom had allowed me a generous monthly allowance for food and fun. I'll admit I skimped by on Ramen noodles more than once to get a sexy pair of heels or new panties.
I continued to spend a lot of time chatting with other crossdressers online. These times would often lead to some webcam fun. I loved hearing their stories of the times when they had met men. I also began to chat regularly with men online. It was quite a turn-on to have them tell me how sexy I was. I loved watching them stroke their hard dicks on webcam.
As the semester passed by, I realized I was getting more and more curious about being with a guy in person. I wanted to know how it felt to be a girl and to pleasure a man in real life. However, I was scared to death about actually doing it. I spent a lot of time looking on the local personals sites. I loved reading the descriptions of what the men were looking for and looking at the pictures of hard, tasty looking dicks that were often posted. Many times I thought about replying to an ad, but I would always back out. Being 5'2" and 120 pounds gave me few allusions of being able to defend myself from some psycho.
In October, I was chatting with Roxanne, a local cd friend. I had met her online during the previous summer. It was coincidental that she lived in the same city where I was going to attend college. After I got to school, we actually met in person. She was in her late 30's and was married. She had been to my apartment a few times and we had dressed and hung out.
I was telling her that night that I really wanted to meet a man, but I was scared. She was giving me advice on what to look for. She said she had met many nice men over the years and that I would too, I just needed to be careful and patient.
Later that night, she sent me a link to a personal ad. I opened it and saw it was a man in his early 50's that lived locally. He was seeking a cute young cross-dresser for regular discrete companionship. He had included a picture. He was a very handsome man.
"He looks nice." I typed back.
"Yes, he does. Maybe you could respond," she replied.
"Should I?"
"What would it hurt? You could get to know him at least." She responded.
We chatted for a bit longer. I kept thinking maybe I should respond to the ad. She was right. What would it hurt? If he seemed creepy, I could always not reply back. I finally told Roxanne I was going to reply.
"Good, sweetie. Just be open with him about everything. If he wants to try and rush you, back off. Okay?"
"Okay."
I hit reply to the ad and began my message.
"Hi! I'm Karlie. I'm a 19 yo crossdresser. I'd like to get to know you better. I'm very new to this. I hope you don't mind going slowly. I look forward to hearing from you again."
Within 5 minutes, my phone beeped. I looked and saw that it was from an unfamiliar address. I felt a tingle as I opened the message.
"Hi Karlie! I'm Richard. It's nice to meet you! I certainly want to get to know you better as well. I'm not looking for something immediately. I want to find someone that shares a mutual attraction and that is discrete and safe. I'm a widower and have never done anything like this. I have attached a couple photos (nothing too racy!!). If you are comfortable, please send me a pic back. I'm sure you're beautiful. "
I was actually smiling at my phone as I read the last part. I quickly opened the folder I kept my Karlie photos in. I scanned through them repeatedly trying to pick just the right one. I felt giddy as I did.
I finally selected two photos. I was in full dress in both. In the first, I was a sexy little black dress I had liberated from my mom's donation pile. I had been wearing tan thigh highs and a sexy pair of ankle strap heels. The second photo I had temporarily died my hair a dark brunette. I was wearing a sun dress, also from mom, and some wedge sandals.
I attached them both and began a reply.
"Richard. That all sounds really great. I want to meet someone safe that I can learn from. I'm really shy about all of this. I love dressing, but I really feel like I want to go a little further. I've attached a couple pics of me. I hope you like. Karlie"
I was greeted with another quick reply.
"Karlie... Oh my god, you look amazing honey... I really mean that. You're really a sexy young lady. It sounds like we are a perfect match. I love you as a blonde. If you'd like, let's get to know one another and get comfortable with each other. There won't be any pressure from me."
When he said that, I felt better. We exchanged emails for a couple weeks. True to his word, there was never any pressure. He was always warm and sweet and he made me feel completely comfortable. We finally exchanged phone numbers and would talk at least once a day.
He was 53 and had been a widow for about 2 years when he lost his wife to breast cancer. He said he had been curious about cross-dressers for a long time, but had never acted on it. He said he had begun to think about it again recently. He had posted several ads but I was the first response he had thought about pursuing.
Finally, after about 4 weeks, I felt comfortable. I knew I was ready to do it. I told him on a Thursday night. He was really excited, but he did ask if I was really sure. I told him that I was. We made a date for 8 at his house on Friday night.
I was too excited to really sleep that night. I probably tried on everything in my closet 3 times. I finally selected a long sleeved black dress. It was very clingy and hugged my body all over. I would wear a sexy black bra and thong I had just recently purchased on-line. I paired them with a lacy, black garter belt and black Cuban heel stockings I had.
The alarm the next morning was a terrible shock but I quickly dragged myself from my warm bed and trudged off to class. After I was finished for the day, I rushed home and took a quick nap. When I woke, I ran a nice warm bath and soaked for a long time. I had shaved the day before, but I ran over everything one last time. I felt like I was super smooth. After I dried, I put on some moisturizer. I looked at the clock and it was already almost six.
I felt really nervous so I poured myself a little glass of wine. It helped me relax as I put my makeup on. I spent a long time making sure everything was perfect. I had selected a deep red for my lips.
I looked at the clock again and it was after seven! I knew I had to hurry. I quickly put my bra and panties on. I had some B cup breast forms that I used. I had wanted to get bigger ones but I didn't think they would fit my slender frame. Finally, I slipped the silky black stockings up my smooth legs and attached them to my garter belt. I had already straightened my blonde hair. I stood in front of the mirror.
"Tonight's the night," I said to myself.
I put my dress on and decided to have another small glass of wine. After I finished, I grabbed a bag I had packed with a change of clothes and snuck out of my apartment to the back stair case where my car was parked.
I quickly drove the 20 minutes to the upscale neighborhood Richard lived in. I found his address and pulled in the driveway. I saw that I was about 10 minutes late for our rendezvous. He had an impressive home. I couldn't wait to see the inside. After looking briefly around, I got out of my car and walked to the door. I felt like I was about to faint I was so excited. The click of my heels on the side walk seemed almost deafening.
I rang the doorbell. The wait for the door to open seemed so long. Finally I heard the lock being turned. Richard opened the door with a big smile.
"Wow! You look amazing, Karlie."
I blushed and simply said "Thanks."
"Please come in." Once I was inside the door, he gave me a quick kiss on the cheek. I was a little shocked at first, but it had been nice. It made me feel better. He was taller than I thought. He was easily 6'2". His photos hadn't really done him justice. He was in great shape, even for a guy 20 years younger.
He took my hand and led me into his spacious great room. There was a large overstuffed couch with a low table sitting in front of it. There were two glasses of wine and some chocolate on the table. I glanced at him and he winked at me.
"I'm trying to be a good host," he said.
"Yes. I see that," I smiled.
He led me to the couch and we sat down. All of a sudden, I felt very nervous again. He offered me a glass of wine and I quickly took a sip to try and calm myself down. We sipped our wine and talked about how our days had been. He was a senior manager for an engineering firm. He knew I was a student and he asked how my classes had been.
I looked around the room and saw pictures of his late wife. I also saw a picture of a girl about my age. I assumed it was his daughter. From a distance, she looked a bit like me!
We chatted a bit more and sipped our way through a second glass of wine. It was definitely having an effect on me. I finally felt like I was relaxed. He leaned over to me and whispered in my ear.
"Karlie. I want you to be comfortable sweetie. I don't want you to feel any pressure."
"I don't. You've been perfect with me," I replied.
"I'm glad to hear that." He began lightly stroking my nylon clad knee. "May I kiss you?"
"Yes," I said, almost breathlessly.
I had only kissed a girl a few times so I was a little unprepared when our lips met. However, I followed his lead and was quickly into the flow of things. Our tongues met and danced. I love the feeling of having this big strong man kissing me. While we continued to kiss, his hand was caressing my arm. He slowly moved it back down until it was on my thigh. He lightly stroked the silky nylon of my stocking.
I found myself quickly becoming aroused. It was making me a bit uncomfortable since my little clitty was so tightly confined in my little thong. I felt Richard's hand slowly begin to make its way up my thigh. It reached the hem of my skirt and continued onwards. His fingers found the welt of my stocking and quickly traced out the clasp of one of the garter straps.
He stopped kissing me momentarily. "I love that you're wearing stockings, Karlie. You don't how sexy I think that is." I managed to smile briefly before his lips once again met mine.
His fingertips continued to move higher along my thigh. I felt an almost electric feeling as his fingers traced along the smooth bare skin above the stockings. They made momentary contact with my swollen little clitty through my panties. I actually shuddered when he touched me. Sensing my enjoyment, he teased me a little more before moving his hand away. I was a little disappointed, but I reminded myself, I was here to make him feel good.
I moved one of my hands to his lap. I found that he was very hard as well. I lightly rubbed him through his slacks. This brought out a deep moan from him as we continued to kiss. I was getting even more excited now that I was touching him and hearing him respond. I continued to rub him for a little while longer. Finally, I couldn't wait any more. I had to see it and have it in my hands.
My hand reached for his zipper and I swiftly pulled it down. My other hand began un-fastening his belt and pants. I reached a hand inside and soon found his rock hard cock. I pulled it through the fly of his boxers and began stroking it. He moaned again.
I looked down at it. He was probably close to 7", but thankfully he wasn't overly thick. I looked back at him and he nodded. I smiled at him briefly before I slid off the couch and knelt on the carpet on my stocking covered knees.
I lowered my face into his lap and examined his cock closely. It looked so good. I stuck my tongue out and licked a drop of pre-cum that I had squeezed out with my stroking. I enjoyed the taste and started licking all around the head. My head spun as I savored the feeling of finally having my mouth on a real, hard cock.
Richard moaned and began to gently rub my back with one of his strong hands. I opened my mouth and slowly took the head in. God, he felt so big. I was thankful I had spent so much time with that dildo in my mouth the last few months. This was so much better though. It was finally a flesh and blood cock in my little mouth. The handsome man continued to gently stroke my back and neck as I sucked on him. He was moaning my name and telling me I was making him feel so good. He even called me baby.
I sucked and slurped on that hard cock. I would take my mouth off it occasionally and just run my tongue around the head, as if it was the last ice cream cone I would ever eat. I could tell he really enjoyed that. I would take him back in my mouth and slowly work my lips back down as far as I could. I wasn't able to get more than about 5" down my throat, but he never complained. I played with his big heavy balls as I sucked him. I imagined they were full of cum for me.
"Oh, Karlie. That feels so good sweetie. This is the best, baby doll."
I moaned around his hard cock when he called me that. He placed his hands on the back of my head and helped guide my lips up and down his cock. When I reached bottom he gave me a little nudge trying to get me to go further. I was afraid of gagging, but I didn't want to disappoint him. I tried to get a little bit more but he was just too thick. I felt myself gagging and my eyes were watering. I quickly backed off.
"I'm sorry. It's just too thick!" I sputtered.
"Mmm, don't worry baby. I'm sorry to push you. You were doing just fine." He reached under my chin and pulled me up a bit before he kissed me again. I loved that. When we broke our kiss, I resumed sucking that hard cock.
I sucked for another couple minutes when I felt him begin to tense up. I was so happy. I knew I was going to make him cum! He put his hands on the back of my head again.
"Ah, baby. That's so good. Here it comes," he moaned. He tensed up even more and I felt the head of his cock begin to throb on my tongue. All of a sudden he erupted in my mouth. I kept sucking just the head as jet after jet entered my mouth. I was trying to swallow some, as it just kept coming. Finally, he stopped. I pulled my mouth off the head and realized I still had about a tablespoon in my mouth. I swirled it around on my tongue, savoring the taste of it before swallowing it down. It definitely tasted different than my own.
I looked up to see him looking at me with a smile on his face. I smiled back at him.
"Was I good," I sheepishly asked.
"Good? You were great baby. Did you enjoy it?"
"Yes. I did. I loved it. It was even better than I thought it would be."
"Come back up here." He reached down and pulled me back up on the couch with him. He quickly kissed me. His hand was stroking my leg again as we kissed.
"My, you're excited." He laughed. I looked down to see that my clitty was making a very prominent bump in my tight black dress.
"Yes. I am," I blushed.
He reached for the wine bottle and poured us another glass. We sipped and talked about what we had done. He asked me if was comfortable with it. I told him I had been afraid that I would feel weird afterwards, but I actually felt really happy. I had made him feel great. He smiled.
"Would you be comfortable going further tonight?"
"Yes. I would." I wanted that more than anything and I told him so.
"Okay, good." We finished our wine and he stood up and took my hand. He led me upstairs to his bedroom. When we got there he took me in his arms and gave me another kiss.
He turned me around and had me kneel on the bed. I felt him pull my tight dress up and I felt the cool air on my little ass. I looked back to see him kneel behind me. He placed his hands on my smooth ass and began to kiss my cheeks. I felt him pull my thong to the side. My little clitty finally found a bit of relief as he did.
I felt his hand wrap around it as he simultaneously ran his tongue across my tight little hole. I groaned and arched my back.
"Richard, that feels so good."
"I'm glad baby. I want you to feel good too." His tongue dove back in and began to probe my hole. I felt like I was in heaven. I laid my chest on the bed and crossed my arms in front of me as I laid my head down. I relaxed and enjoyed what he was doing to me. I couldn't believe how good it felt. He kept telling me how sexy I was and how much he wanted me.
I felt a cool liquid being dripped down my smooth crack. The fingers spread and then began to massage the liquid around my hole. One finger began to slowly enter me. I had penetrated myself too many times to remember, but having someone else do it was a new experience entirely. Soon I could feel the knuckles of his hand as he had buried his entire finger in me and worked it around inside. He continued to treat me with the sweetest comments.
I felt myself began to relax from his efforts. He began to work a second finger in me. His fingers were much thicker than mine and I felt myself stretching. I was still laying on the bed as he finger fucked me.
"I'm going to use a toy on you. Is that ok?"
"Mmmhmm." I replied.
I felt the hard tip of a dildo be inserted in my tight little hole. I arched my back as it entered me. He began to stroke it in and out. Damn it felt good. I felt like I was relaxed. I looked back over my shoulder at him.
"Baby, are you ready for me?"
"Yes, Richard." I nodded.
He stood up and finished undressing. I watched as he unwrapped a condom and put it on. He quickly lubed his big cock up.
He placed his hands on my slender hips and pulled me to him slightly. I felt his cock slide gently along my smooth ass crack. It was well lubed, and moved with very little friction. The soft spongy head was circling my little gurl hole. He moved into the center and it felt him slowly begin to apply pressure. I had felt like I was pretty loose, but the head of his cock was slightly larger than the dildo he had been using. In fact it was larger than any toy I have ever got inside me.
The pressure continued to build.
"Just relax baby. It'll be fine."
I nodded my head in response. I closed my eyes and concentrated on relaxing. Without warning, the head suddenly popped past my tight little ring, and he was inside me. I moaned softly.
"Ah."
"Yeah. Me too."
He continued to push softly into me. He paused occasionally to allow me to adjust to the sensation. I felt fuller than I had ever felt. Just when I felt I couldn't take any more, I felt his hips against my ass. He was all the way in me.
We stayed like that for a minute or two before he slowly began to pull back out. He began to slowly fuck me. I had experienced toys many times, but this was the best feeling I ever had. I loved having his strong hands hold my hips as he pumped inside me. I had finally found what I had been wanting.
I realized my clitty was painfully hard. Everything that had happened tonight added to his big hard dick inside me had me so turned on. I reached my hand back to touch myself. He noticed what I was doing and he reached down to push my hand away.
"Let me do it baby." I moaned and nodded my head and in agreement
I felt his large hand wrap around my hard clitty.
"Oh, Richard, it feels so good." I felt myself tense up. My clitty jerked in his hand and I shot my gurl cream. He pulled his hand back out and brought it to my face. It was covered in my cum. I began to lick his hand clean. It was interesting comparing my own cum to the generous load he had fed me earlier.
I was relaxed even further by the orgasm. He used this to his advantage as his paced quickened. I loved the sensation and the sound of his hips meeting my ass as he fucked me.
"Oh, baby. Your tight little hole feels so good. I'm going to cum."
"Please, can I taste it again?"
"Sure." He pulled out of me. I felt so empty, but my desire for another taste of his hot cum was all I could think of. I slid off the bed like a little porn slut and knelt in front of him. I watched as he yanked the condom off. I quickly took him in my mouth. His cock was covered with a wonderful, slimy layer of pre-cum. I took his smooth balls in my hand as my mouth worked up and down his hard shaft.
I looked up at him as I sucked. Being able to see him as I sucked really drove me wild. I moaned as I throated him.
"Karlie, baby. I'm going to cum."
"Mmm," I moaned.
I felt his cock begin to throb. I felt a little blast hit my tongue. It wasn't as big as the first load but I quickly gulped it down like a good gurl. I licked and sucked him until he went limp. He reached down to pick me up. He gave me a long, lingering kiss.
"Would you like to stay here tonight my dear?"
"No, I better go home. I have some things I need to take care of in the morning. I'll take a rain check though."
"Most certainly. I hope this will be the first of many meetings we share." He smiled sweetly.
"Yes me too." I had adjusted my clothes and we walked back to the entry.
He told me good night and gave me another long tender kiss. I walked out of his big house and quickly to my car. On the drive home, I replayed the evening's events in my head. It had been so good.
When, I made it home, I poured another glass of wine and drew myself a warm bath. I realized my little pussy was sore when I sat down. I guess I would get used to that. I had gotten my first taste, and I had loved it. I couldn't wait to do it again.
I was laying there with my eyes closed when my phone beeped. I picked it up and saw it was a text from Roxanne.
"How was it?" She asked.
I quickly filled her in on the details.
"Good for you gurl. That sounds wonderful. I won't keep you, I just wanted to make sure you had a good time and made it home safe!!"
I texted her back thanking her for all her help and support. "Don't mention it!" She replied.
After my bath, I put my usual pajamas consisting of a silk slip I had gotten from mom and a pair of suntan sheer to waist pantyhose. I was still thinking of being on my hands and knees getting fucked when I fell asleep.