Feminine Enough Ch. 01

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Chris dresses to please a roommate.
1k words
4.4
108.1k
39

Part 1 of the 3 part series

Updated 09/30/2022
Created 11/15/2012
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When we moved in together sophomore year, i never expected things to turn out as they did. Justin and Chris and I had been on the same floor in the dorm freshman year, and when the house opened up right after we all decided to stay over the summer, we jumped on the lease.

Chris was openly gay but that didn't bother Justin or I. We just laughed off his standing offer of "an enthusiastic toe-curling blow job," an offer he periodically reiterated. "You'd need to be a LOT more feminine for that to ever happen," I'd declare. "A lot."

None of us had summer classes, so other than our part-time jobs, the hours were spent playing video games, lounging at the lake, and drinking beer. One Saturday we went to a party at Hannah's house and I got a little too drunk and walked home alone. There weren't any good chicks there, anyway, except Hannah, of course, but she was all over some douchey frat boy that night.

The next morning next morning I was in the kitchen, nursing my hangover with a cup of coffee and shooting the breeze with Justin. He was acting a bit strange, but I figured he was also feeling the results of the previous night's revelry. When Chris walked in and Justin abruptly jumped up and left the house without a word, I knew something was up.

"I sucked his cock, of course, and I think he's worried about how much he liked it," Chris volunteered. "You straight guys are just weird. What's the big deal?"

Things were a bit uncomfortable for a few days after that, with Justin not making eye contact with Chris and generally avoiding him. I stayed out of it until I got sick of not being able to hang out with them both at the same time.

"Just tell him it was a one-time thing and that it won't happen again," I told each of them separately. "It wouldn't have to be a one-time thing if he wasn't so weird about it and just relax," Chris countered. "You could be less of a prude yourself," he added. I laughed and passed it off with my usual reply.

"Please, just talk to him so we can get back to normal?" After that there was an uneasy truce until another week or so had passed and Justin was able to pass it off as a drunken mistake.

One lazy Saturday afternoon after that, I was napping on the couch and awoke to a warm body pressed to mine. A smooth, silk-encased calf slid sensuously against my leg while a slender hand rested lightly on my thigh.

"How do you like it?" a husky voice purred in my ear, her warm breath on my neck. I turned my head, and it was Chris, dressed in a skin tight tube dress, black stockings and pumps, with a blond bob wig. I have to admit, the dress clung to his slim form and the stockings and pumps accentuated his long legs. I can't honestly claim that the hardon that was stirring could entirely be attributed to having just awoken.

"I think you do like it," she said as her hand slid up the leg of my shorts to stroke my thickening cock through my briefs. "I think you like it a lot." She slid onto her knees and ran both hands slowly up and down my thighs, forcing them apart to make room for her.

"Is this feminine enough for you?" Her hands undid the button and zipper of my shorts. "Are you ready for the blowjob of your life?" Her pink lips parted in a sultry smile when she saw the taut outline of my cock straining against my briefs. "Looks like the answer is yes."

Her hands gripped the waistband of my briefs and shorts and gave a short tug. I arched my hips off the couch a little to make it easier for her to tug them both down to my ankles.

A slim hand grasped my shaft as she leaned forward. "Mmm, I've wanted to do this for a long time." Her pink lips hovered less than an inch over the tip of my cock, and I could feel each warm, excited breath. "I want you to sit back, relax, and enjoy this. If you don't want to do it again, that's fine, but just enjoy right now."

Her hand slid slowly up the shaft and her tongue darted out to catch the drop of precum that glistened at the tip. "And of course you can cum in my mouth," she added as that warm mouth enveloped my cock. Her pink lips stretched around the shaft as her head went down and her cheeks hollowed slightly as it came back up from the suction she was applying.

I was bewildered--moments before I had been napping and suddenly I'm getting the most fantastic blowjob from a hot woman who also happened to be my roommate. Very quickly though, all thoughts left my head as Chris applied herself to the task at hand.

That warm, sensitive mouth was doing things to my cock I didn't think possible. Her lips slid all the way to the base with each bob, easily two inches farther than any of my ex-girlfriends could take. She fell into a rhythm of three head bobs up and down my cock, holding it for a five count at the bottom of the third to swirl her talented tongue against the shaft. I think I could feel her throat muscles caressing the tip, but there was just so much pure, wet hot sensation going on in there, it's hard to say.

Her hands gripped each of my calves as she worked her magic. No hand action here--it was all eager lips, tongue and throat. As the minutes passed, my breathing gradually quickened. Chris started adding a little moan at the bottom of each head bob. "Mmm, mmm, mmmmmmmmm." I felt my balls tighten as my orgasm throbbed across my chest, down to my toes and out, with six shuddering spurts into Chris' welcoming mouth.

Chris' lips left my cock for the first time since they first touched it. She ran her thumb from the base of my shaft to right up under the head and her soft pink tongue darted out to catch the last drops as a smile spread across her face. "I really hope you want to do that again sometime."

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10 Comments
liz33ndliz33ndalmost 9 years ago
nice story

it could use more lead in and seduction, but still a good read.

Cummer2Cummer2over 9 years ago
Nut-draining excitement!

You have a gift, my friend. It's my fantasy to have my dick drained by a TS roommate.

AnonymousAnonymousover 11 years ago
Holy hell

More on this one! God, that story is exceptional. Though not what I would consider gay myself, I suppose I have an alter ego almost, who is a sexy and uber-feminine woman called Julia. I like to think that this is who Julia would be, since I could never be this brazen and openly sexual. Julia is the slut I always felt I needed to be, and also significantly hotter than I, and this story definitely added to who Julia is!

Joannemitchell67Joannemitchell67over 11 years ago
Heavenly

Well done. Captures it beautifully. As a long time crossdresser, I loved it. I had a room mate in my early 20s that was deliciously handsome, oh how I wish this had happened with himm !!! Frustratingly, at that time I was still not "out" with my sexuality and all of my crossdressing was done in private.

If I had my time again I would be more forward. :-)

Joanne

Joannemitchell67@yahoo.com

AnonymousAnonymousover 11 years ago
a cd whore

great story and very realistic in the way it happened. as someone who began sucking cocks at a very young age. Eventually, the sucking lead to crossdressing since guys were more likely to give their cocks up. Of course, this lead to providing my ass pussy to any and all that would fuck me. I found that there were never enough cocks for my mouth and my ass to satisfy me. I became the neighborhood whore and loved every day of it and I still do. the feeling one gets when dressed as a female slut and know that with little effort you can have your ass pussy and mouth filled with nice, hard cocks. I still love it.

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