This is a story about a first time cross dresser and some sexual firsts that happen during the experience. It is intended for mature audiences. If you are not into this sort of thing, or are under the age of 18, please stop here and find something else to do. If you are, I hope you enjoy! ;)
The five years since that first smile, on her first day, across the line of plates in the Applebees' kitchen had been filled with drugs and booze. This family of misfits and screw ups buzzed with questions and theories about the cute girl with the tight pants that had walked into our home. Getting the new server to come to the after work party produced a rush of excitement every time, and Cheryl was no exception. Rides were offered, then directions were given. Approval for the boyfriend to tag along disappointed some, but surprised few.
I met her at the door, shy at first, she opened up as the shots started flowing. Chain smoking on the patio with beers blossomed into instant friendship as we joked about the ridiculous antics of our pasts. Boyfriends and girlfriends came and went in our lives, but our relationship stood strong against life beating away at us. Our drunken hookups and after bar romps may have outnumbered the late nights crying over exes, but nobody kept score.
When we found ourselves in fairly serious relationships and looking for a place where a beer pong table wouldn't be our primary living room furniture, the four of us renting a three bedroom house seemed like a great idea. Sylvia and I shared the middle room in the back corner and turned the small room into an office so she could have a quiet place to do homework. Cheryl and Roger shared the master suite down the hall on the other side of the bathroom.
Sylvia had been at a work conference for three days during her spring break when I found myself soaking my feet with Cheryl in the master bathtub and putting in work on a bottle of peach flavored vodka. It was the middle of the afternoon on a Wednesday, but since neither of us had work until Friday evening, getting drunk seemed like a fine idea.
BEEP BEEP
"That's Roger," Cheryl sighed setting down her phone. "He's going to be late, but at least he's bringing pizza."
"Tell him he might want to pick up another bottle, and a case of beer too." I replied with a devilish look as a poured out two shots.
BEEP BEEP
"Drink water." She laughed, "what an ass."
We tapped our shot glasses and emptied them quickly before continuing our conversation about life and love and whatever happened to cross our minds. Eventually, she began her process of primping to get ready for Roger's emminant arrival. We had never been shy with each other, so I barely took notice as she stripped and slid into the tub. After toweling off, she grabbed her razor. Her hands were smooth and quick as she took off all the hair below her waist.
She sauntered over to her closet and grabbed a short denim skirt with a white tank top. The smile and wink she gave me as she looked back while bending over to pull up her lacy pink thong almost pulled me off the side of the tub. After her make up and nails were done, she pulled out her hair straightener and ran it through until her jet black hair hung to the middle of her back. With a quick spin, she looked at me. "Do you think he'll like it?"
"You look fantastic, he's an idiot if he doesn't." I flirted as I poured another round of shots from the nearly empty bottle.
"Let me do your hair!" She giggled, "How have I never done your hair in five years? Come sit here." She put her hand on the side of the tub near the counter with her hair equipment.
"You braided it for me when I went as a viking two halloweens ago." I quiped back.
"Ok, but I think this will look really cute on you." She brushed it out and quickly took to straightening it. Almost as soon as she finished we heard the front door open. "We are back here honey," she hollared to Roger.
He stepped into the room with a bottle in one hand and a case of beer in the other. "Looks like you two have been having fun." He said with a grin as he surveyed the mess of hair and make up products. As he set the beer in the mini fridge, he turned back and added, "Cheryl, you look incredible!"
Her smile lit the room as she skipped over and jumped into an embrace with him. "We're going to have fun tonight," I could hear her whisper to him and then slightly louder, "what do you think of Tim's hair?"
"Looks good like that, better than the ponytail he normally has it pulled back in." He turned towards me, "it's different than I'm used to, it looks a little girly, but you pull it off well."
"Thanks ... I think," I replied smiling at him. "You're way behind her though, you need to play catch up." I poured the last two shots out of the bottle and brought them to them.
Cheryl grabbed both and fed them both to Roger. "Now go shower," she told him, "lets get you cleaned up so I can have some fun." Taking the bottle from his hand, she led him towards the shower. After dropping the bottle in our bucket of ice, she began to peel his clothes off while kissing him passionately all over his body. I began my journey towards the kitchen to check for the pizza when I heard the shower door close and Cheryl asked me, "where are you going? This bottle ain't going to drink itself."
The empty bottle was thick on my head as I walked past the steaming shower towards the bathtub and fresh bottle. I retook my seat near the counter as she poured another round of shots for us. She picked them up and fed them one after the other to me just as she had done moments ago for Roger. She reached up and pushed the hair behind my ear. Her smile was mischievous as she looked into my eyes. "This style is kind of girly, cute, but I think it needs some work. Let me dress you up."
"Oh, I don't know," I laughed. "I think I'll let you guys have some privacy. He seemed pretty worked up when he saw the way you looked."
"He can wait, he has all night with me," she teased. "Come on, it will be fun." She grabbed my elbow and started leading me towards her closet. Once inside, I felt her nimble fingers work their way down the buttons on my Hawaiian shirt and then onto my shorts. After the she ripped the zipper open, my shorts fell to the floor and she tossed the shirt off my shoulders. The delicate index finger of her right hand traced a line down my chest and hooked the waist band of my boxers. As she yanked them to the floor, she gave a quick kiss just below the waist line of my now naked body.
The tips of her jet black hair brushed my chest as she stood and turned to find what she wanted. Soon I was holding a new outfit and she stood there with her hand on her hip and a look on her face of pure impatience. I sighed and pulled the pink wife beater tank top over my head before stepping into the knee length blue skirt with the large pink flower on the left thigh. She had worn this outfit to the music festival we attended the previous summer. Loose fitting and flowing on her, the skirt sat tight on my hips.
The alcohol, her kisses, the outfit she was wearing, and the naughty nature of what we were doing had caused me stand straight up tenting the front of the skirt. She stroked my manhood through the silky smooth fabric of the skirt and whispered in my ear, "well this isn't very girly. I think I know what we can do about this." As the words carressed my ears, her hands lifted her skirt and shimmied her panties down her legs. She held them open for me at knee level and waited patiently for me to get the idea to step into them. After tucking me into the panties, she gave me a quick look over and with a satisfied grin and a wink decided, "Roger's right, you do look girly."
"Have you had your fun?" I chuckled as I began to remove her shirt from my chest. "I better get changed before he's done with his shower."
"Oh no you don't!" She proclaimed as her hand stopped me. "We still need to do your make up." Again she grabbed my elbow and began leading me out of the closet. As we stepped out, I looked at the mirror and was surprised to see that I didn't look half bad. I was not passable as a girl in good light, but I might confuse a drunk guy at a bar. Hell, I had hooked up with girls that didn't look this good.
Obviously tipsy, she was quite heavy handed as she painted my face. Smokey blue eye shadow to match the skirt and a generous amount of bright pink lipstick completed the look she had designed for me. She pulled out her phone and snapped a quick picture of me. "I like it!" she giggled as she looked me over. "I think Sylvia will too. Next time we'll have to make sure to shave your legs though."
"Yeah, next time." I replied as I rolled my eyes at her. "I have to admit, I didn't think I would look this good. You did a pretty fantastic job with what you had to work with."
"Thanks, pour us some shots, I'm going to grab a beer for Roger. He should almost be done with his shower." As I reached for the bottle she slapped my ass. "Thata girl!" she laughed as she walked away.
My embarrassment probably glowed like red light bulbs in my cheeks, but it was all in good fun. I was sure we would have many drunken nights in the future laughing and retelling this story. She returned with the beer just as Roger stepped out of the shower, towel around his waist and a surprised look on his face. He looked at me and laughed, "wow. You two are having fun tonight."
"So what do you think honey? Is Timmy cute as a girl?" She asked him as she handed him his beer. "Do a quick spin for him Timmy." I shook my head and turned around in a circle. "I'm never going to live this down, am I?"
"I think you look great, not as cute as Cheryl, but definitely the second cutest girl in the room." He grabbed Cheryl's ass and kissed her cheek. "But I think Timmy is not going to work, how about Tammy?"
"Yeah, Tammy! That's good." Her hips shook as she walked back towards me. She got right up to me and pulled me close with an arm around the small of my back. The shot was in the air as she proclaimed, "to Tammy!"
"To Tammy!" Roger laughed in reply.
"To Tammy!" I reluctantly agreed. We emptied our drinks and I excused myself to the restroom. Half drunk, I sat down on the toilet and contempleted the situation I was in. I made sure to wipe the last drops of pee off of me before pulling her clothes back up so I wouldn't ruin them. I stepped out and was only half surprised by the scene I walked into.
Cheryl was on her knees with Roger in her mouth. His towel was laid out on the floor behind him and his head was tilted back as he sipped on his beer. "Hey Tammy," he called out as he heard the door open. "How about grabbing me another shot? And one for Cheryl too."
"Yeah, sure thing." I replied walking back to the glasses. She kept right on working as I brought the shots over to them. He took his quickly and I held hers out for her while trying not to stare at the show going on before me. Her hand reached under my skirt and teased me as his cock slipped out of her mouth and into her other hand.
"My hands are full." She smiled. "Drink it and share it with me."
I looked at Roger and he just kind of shrugged. Cheryl and I had done this before, but I wasn't sure how Roger would react as this technique usually ended with us sharing the shot in a passionate kiss. I poured the shot into my mouth and crouched down to kiss it into her mouth. Just before I made contact, her hand came up from under my skirt, caught me behind the head and pulled me down and off balance. Her tongue reached lustfully into my mouth to lick up the liquor as I fell to my knees in front of her. She held me tightly against her mouth kissing and licking long after we had finished the shot. I began to pull back as the realization that Roger's cock was inches from my face as I kneeled in front of him swept over me. "Don't go." She whispered pleadingly between kisses.
In the back of my mind I might have known what was coming next, but the alcohol and her pleading compelled me to continue this kiss. Soon I felt it. It was subtle at first, just a slight touch on the side of our lips as we made out on the floor. In the corner of my eye I could see her hand stroking his cock as it became every so slightly a more prominent part of our lustful exchange.
As the tip broke the seal between our lips, her knuckles would lightly caress my cheek with each up stroke. Her tongue licked my bottom lip as she wrapped it around him. For just a moment, half a breath or less, she broke off. "Lick it." She moaned at me before thrusting her tongue back into my mouth. I opened my mouth slightly to stick out my tongue and felt the pressure of her hand on the back of my head as his member slid past my lips. My lips touched her knuckles as her hand slid down his cock. Her gentle embrace pushed me forward as he slipped deeper into my mouth.
When he reached the top of my throat, I began to pull back from him. Just before he fell out of my mouth, I felt her firm pressure on the back of my head again. She brought my lips back down his shaft until he filled my mouth again. I came up a second time, but was met with the same consistent pressure. This repeated a few times until I submitted to this task. She kept a steady rhythm for me and was consistently firm when the tip reached my lips. "This is so fucking hot." She whispered between kisses at the base of his cock.
After a few minutes of bobbing my head up and down on his member, I could hear him moaning in pleasure. The satisfaction I felt surprised me as I continued my work. She moved her kisses up my cheek and to my ear and started nibbling and kissing around my ear. Just before he reached the top of my throat I heard the words and felt a renewed strength in her grasp. "Swallow him."
I wasn't quite ready for his cock to slip into my throat and it caused me to gag a little, but I did as she said and swallowed which made it a little easier. With all seven inches of him in my mouth and throat, I could feel him pressed against my nose. She held me there for a moment before letting me pull back. As two inches slipped past my lips, I caught a breath and she pushed me back down onto him.
He would slide into my throat, she'd hold me there for a moment, I'd pull back for a quick breath and then I would be pressed back into him. As I adjusted to the rhythm she no longer needed to force me into him. She would let me pull back further and then I would return to bottom of his shaft. Her free hand grabbed his and I soon felt his hand on the back of my head with hers.
As her hands left my head and he took control, the intensity of the situation increased dramatically. I had maintained a slow and steady pace, but the strokes now had a fevered urgency. Taking the tip of his manhood into my throat being slightly uncomfortable was easy compared to having it shoved in and his cock buried inside me. He would pump a few times deep into me before pulling me up just to drive it down again.
Cheryl grabbed the shot glass that had been forgotten in my hand and I could hear her kissing him above me. "Your cock looks so good in those bright pink lips, don't you agree honey?"
"Yeah," he moaned. "He's a natural," barely escaped his lips as I started to look up. "This feels amazing," came breathlessly as I made eye contact with him. With both of their eyes locked on mine I looked back towards cock just as it thrust deep into me. "Oh my god that was hot! Watch his eyes as you suck him Tammy. Watch the pleasure in his face." She placed her hand under my chin and lightly tipped my face upwards until I was staring back at him.
He looked so satisified, his pleasure all consuming. "I can't wait to paint his pretty face," I watched him whisper to her as he pumped into me.
"No honey, I want you to cum in his mouth," she replied with a devilish grin. "I want to share your seed with him," she added as she walked back to pour shots.
Looking into his face as he watched her walk away the realization of what was happening swept over me. I was no longer being teased and pushed into this by Cheryl, I was in a skirt, on my knees, sucking Roger's dick. There was an end game to what was happening. It had never occured to me that I would be finishing him off, until the moment they discussed where he would finish, I had assumed Cheryl would eventually take over.
She returned and I watched as she fed Roger his shot. Her arms wrapped around his neck and I felt her start to grind her pussy into his hand on the back of my head. "Are you close honey?"
"Yeah ... almost there ... " his words and his pace were increasingly urgent.
As she stepped back, I watched as she grabbed his free hand and placed it with his other hand. "Fuck his face Roger," was muffled as his hands covered my ears and ran a deep full stroke into me. And another. And another. Faster. "Hold it in your mouth." Faster. "I want to share it with you." Deeper. He thrust, and shook, his eyes rolled back, and my mouth was flooded. It wasn't a squirt gun blasting the back of my throat as I expected, it was a sudden fullness of liquid. He pumped and pumped again and then his grip went soft.
As his cock left my mouth, she knelt next to me. She poured her shot in her mouth and pulled me into her. His salty sweet semen mixed with the vodka in our mouths. Our tongues probed each other as we swapped the liquid back and forth. Soon she pushed it all into my mouth and broke off the kiss. "It's so sexy that you did this with me," she whispered as I swallowed everything. She grabbed Roger's softening cock and kissed the tip, brought it up to my lips and gave me a sly wink, so I did the same. After standing, I took her extended hand and she led me to the bed. "Now it's time for you to taste your own load."
I hope you enjoyed reading this as much as I enjoyed writing it! This is my first submission here and if you have any feedback, I would welcome it at Tammy.Lyn.1981@gmail.com . I have a few more chapters that I am working on and hope to publish soon.