tagTranssexuals & CrossdressersRachel's First Time

Rachel's First Time


I'm one of those lucky guys who gets to live with a model. We have one of those spacious apartments that's like a house inside. I work as a data entry specialist for a big firm, the bonus is that I don't even have to leave home for work; I just log in for a few hours a day, type information into a database for a bit, and pull in an easy $10,000 a week. Megan, my roommate, had one of those great figures us men all lust after. And to be truthful I always wanted to take her down.

Megan and I have a very friendly relationship. She considers me one of the gals, and confides everything in me. I was the first person, besides her lover, to find out that she was a bisexual. She really trusted me with everything. I'm always there for her, I hold her when she's down, we kiss sometimes but we never went any further. We both wanted to, but we held back because of that friend barrier that always pops up.

Now for me... Well, Megan likes to tease me because I look like a girl. My face is very feminine, and I have a curvy waist like hers, not quite so pronounced, but nevertheless it's there. I let my hair grow longer, and she keeps puling it back into a pony tail saying it made me look very pretty. I kept the hair like it, any excuse to have her close. But all this teasing awakened something within me. Something I had once thought was sordid.


One day during the summer, Megan received a phone call from her agent. It was obviously some kind of job. I did my best to listen in, wondering how long the job would last. Her agent had one of those dainty voices that you wouldn't hear if the T.V. was on too, so I never caught a word.

Although, I know I didn't really need to. As soon as her agent was off the phone, Megan plonked herself down next to me, gave me a hug and told me everything.

'That was Elise,' which I already knew because I had answered the phone. 'She says Cosmopolitan wants me specifically for this shoot down at the beach. Could get very hot!' she said. 'Want to come?'

Yes, actually I thought, but then a voice I had heard more and more over the past weeks cropped up again.

'I would... but I have to go online and get some work done. I've neglected it a bit,' I lied.

Megan pouted slightly in that oh so sexy way she did. How I wanted to kiss her gorgeous full red lips right then!

'Okay then,' she said sadly. 'That's important. I'll see you when I get back.'

'Okay gorgeous,' I flirted. 'I'll be here when you get back!'

Megan slipped me a quick half smile as she scooped up her keys and made for the door. I followed her out to say goodbye. And once I saw her slinky convertible pull out of the garage and round the corner I was straight back inside, but I didn't go to my computer.

Less than a minute later I was rooting through Megan's wardrobe, pulling out dresses, pulling them against myself and then slipping them back in as they were. I felt bad going through her clothes, but I couldn't help myself. Part of me just felt that I should be in them.

I decided finally on a pink ruffled knee length skirt and short white strapped vest top - very sexy. Next was underwear. Fortunately, in size Megan and I were a similar size, as I noticed time to time from her strutting around in my clothes. I pulled out a lacy pair of black panties and matching bra. A hint of naughtiness underneath an innocent wrappings.

Delicately, I pulled the panties up my legs, fixing my cock between my legs, and holding it in place with Megan's panties. The bra was no trouble either, thanks to many hours practice with the one she had "lost" from the dryer. She wasn't a small breasted girl, but I was still able to mostly fill out her moderate bra without any additions. Over the panties, I pulled the sensuous ruffled skirt on. It felt great against my legs, and the slight breeze from Megan's open window was amazing too; especially when it circled up under the skirt and blew against my tucked away surprise.

I had just pulled the white top on when I spotted Megan standing in the doorway. I freaked out all of a sudden. I thought about running, but my legs wouldn't move. I could feel my stomach rising into my throat. Was certain she'd flip out, but she just smiled at me.

Even though I was terrified, and humiliated, I found myself feeling highly aroused to. The tuck job I had done was slipping loose.

'Hmm,' she said. 'So this is what goes on when I go out?' I wasn't really sure this was a question. Though the smile never left her face. 'Do you feel like a woman now, or do you need more?' That was definitely a question.

I couldn't speak.

'Do you have a name?' she asked, stepping closer to me.

'Ra... Rachel,' I stammered. 'My name is Rachel.'

'Well Rachel,' she was still smiling. 'I think you look very sexy in that outfit!' I couldn't believe what I was hearing. She didn't mind me dressing in her clothes. In fact, she seemed to like it. 'And are you a woman?'

'I... I think so,' I said, being honest with her for the first time in weeks.

'Doesn't look like it to me!' she teased. My erection had lifted the front of the skirt a little, she could see the protrusion.

She had come close enough to hold me. But she didn't. I was going mad being this close and feeling this sexy in her clothes. I wanted to reach out and take her in my arms, but I still didn't move. Then she spied my clothes on the floor.

'Okay, Rach,' she said, giving me a kiss. 'Stay here. I'll be right back.' She left the room with my clothes. I was still frozen to the spot.

A few minutes later, Megan returned from wherever she had gone dressed head to toe in my clothes. She wasn't masculine, but in my clothes with her hair tied back she could have played the part well... she even walked like a man. She adjusted the crotch of my jeans just as I did when I felt aroused.

She sat me on the end of her bed, pulling her make up kit from her dresser.

'Now to complete the look,' she told me.

We started off with a basic foundation to bring out my natural color, and accented it with a little blush. She applied a little blue eye shadow to my eyelids, tell me it enhanced my deep blue eyes, and stretched my lashes with a good dose of mascara. She finished this combo off with a hint of lipstick.

Looking in her mirror, even I had to admit I was pretty in a girly way. She stood behind me and tied my hair back with one of her scrunches. She left me with two short bangs too.

'There we go,' she commented. 'Perfect!'

I had to agree. I looked pretty, and dare I say it... sexy. If I had met myself, I would have tried to pull me.

'Now what?' I asked her nervously.

Megan pulled her old camera out of her cupboard. It was one of those expensive ones that all the big name photographers were using. She clipped the roll of film in the back and stood ready to shoot.

'You know what I want,' she told me.

Having been to many of Megan's modelling jobs I had seen the sorts of things the photographers wanted. And during previous excursions in Megan's clothes I had practiced a few of them.

One by one I struck each pose. Megan was clearly surprised by how model like I was as she was snapping away with her camera. Quickly, that first roll of film was used up. She pulled a shoebox from under her bed and spilled a load more onto her luscious pink covers. She loaded up a second roll and told me to undress... slowly. I was more than willing to oblige, she had that twinkle in her eye.

As she began clicking away again, I pulled the skirt down, letting it slip past my thighs to the floor. I could see Megan's wetness seeping through my jeans. This made my cock stand out more in her black panties.

'Now for the top!' she commanded.

Sexily, I pulled the top up, revealing the bottom of my lacy bra. As I pulled the vest top higher, Megan saw how my own chest filled her bra. She leant forward slightly, snapping more pictures.

'Damn it!' Another new roll of film. She couldn't take her eye's off my breasts as she fumbled the new roll into the camera.

Once ready again, I unclipped the bra and pulled it forward, letting my humble breasts fall free. My nipples were hard, and from Megan's flicking tongue, I could tell she wanted to be sucking on them.

'Lay down,' she said seductively. 'And give me some real money shots!'

Doing as I was told, I went over to her bed, I stared down my back at her, my hand rubbing at an imaginary pussy between my legs. Megan's hips bucked. I flipped over onto my back and kept rubbing between my legs. The wetness in my jeans had become a patch. I was really exciting this woman. And that made me harder than I'd ever felt.

Megan couldn't take it anymore. She threw her camera to the side and lay down on top of me, her tongue pushing its way inside my mouth. I kissed her back, letting my hands run over her back to her perfectly shaped ass. She pressed her groin against me, I felt her moisture, she felt my twitch.

Still kissing I pulled my shirt up over her head, pulling out the band she had tying her hair in place. Her hair fell forward and curtained my view. My god, we had kissed before but I would never have guessed she could be this passionate.

Anxiously the two of us undid the jeans and I pulled them down her legs, kissing down her beautifully tanned body as I went. She quivered with every kiss. There was no wonder she had made my jeans so wet, she had gone commando in them. She returned the feeling I gave her, kissing down my body as she pulled her panties away from my crotch.

Laying her down, I rested between her glorious legs. My cock was just inches away from her glistening pussy, and he twitched every second that he was there. Insisting on being pushed in.

'Not yet!' Megan snapped. 'First I want your breasts. And then I'm going to fuck you!'

She gave me a light smack across my ass. My cock twitched again.

Megan flipped me over, sliding her body up against me, she descended her kisses to my breast, lightly kissing and sucking towards my tiny nipple. I let out a moan as she took my erect flesh in her mouth, running her tongue around it. I couldn't help myself, my hand dove at her pussy, forcing its way inside her delicate folds.

Megan rewarded my touch with a gentle bite. I never knew how much pleasure I could feel just from my nipple, and Megan seemed intent on showing me just how pleasurable it could be. If I wasn't careful I might have come just with that.

As my breathing became shallow, Megan eased the pressure on my nipple. Her mouth worked its way back to my lips, her tongue finding mine again. She brought her groin fully against my leg, her juices mingling with my almost invisible hair.

Her breathing was the same as mine, short and shallow, filled with desperation. I wasn't the only one who had been lusting. Megan had wanted me too.

I whispered my need into her ear. She nuzzled hard into my neck, lifting her groin from my leg and sliding across me. I felt the brush of her tender flesh as she rested her legs on either side of mine, her pussy pressing against my now desperate member.

'Be gentle,' I teased as she guided my twitching cock inside her very wet hole.

Ignoring me, Megan drove herself hard onto me. She pushed herself upright and took even more of me up inside her.

'Like that bitch!' she said slapping me across my face. I wasn't going to deny her, being submissive like this was really getting me going. I was loving it, and clearly so was Megan.

She lifted herself up, almost pulling me out, then drove back down again, taking all of me back inside. We both groaned loudly. She carried on driving. And I just couldn't get enough, even when she slapped me for pushing with my hips.

'You're a woman! Now act like one!' she shouted, thrusting me deeper inside.

That was it for me... woman or not, I had the cock and I was in control. Megan screamed as I threw us over. We rolled off the bed, slamming my back into the floor, but I wasn't done. I rolled her again and used my weight to hold her down.

'You may be the man,' I told her. 'But even you can be fucked!'

Her only response was a loud moan that sounded like "see if I care" as my cock pounded her perfect pink hole with its red inner lining, her wetness splashing over my balls. I could feel her pussy clamping down onto me, holding me in place. I could only move a little inside, Megan knew what she was doing, and she enjoyed every second of it. As did I.

The extra friction from her tighter pussy brought the final squeeze we both wanted so badly. Megan never released her grip, she wanted my cum inside her warm pussy, and I was in no position to deny her. Nor did I want to.

I pushed in harder, forcing her pussy muscles to relax. She groaned, still trying to keep herself tight for me. I pushed harder, again forcing her to loosen. My cock slammed against her deepest insides, pushing. She flexed her hips too, matching me thrust for thrust, parting her legs as wide as she can, making it so easy for me to get deeper.

I let out a deep groan as I shot my load deep inside her gushing pussy. Our juices mingling together inside Megan's love basket. She pulled me into a hug, not letting me off of her. Our ragged breathing slowed in sync as our breasts rubbed together. Already, I felt myself going soft inside Megan's sweet pussy, the smell of sex filling the air around us, adding fuel to the loving kiss she gave me. When I climbed out of her, I lay back down beside her and we feel asleep in each other's arms.


Later that day, when she woke me with another deep kiss, I saw more beauty than I had ever seen before within her features. I guessed that was the effect of the love I knew was growing in her heart and soul, the love that my own was fast matching. Staring into her eyes, a question suddenly occurred to me, one I should have asked hours ago.

'How come you came back so early?' I asked. Megan smiled.

'I never went away. I drove around the block and then came back to watch you!'

I'd been set up, but you know what... I didn't care cause I had just made love to the sexiest, most gorgeous woman on the planet. And she loved me back!

Report Story

bydarkphyre© 4 comments/ 79784 views/ 11 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartwolfblade88, rjm0099 and 9 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (4 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (4)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: