I'm at college supposedly studying to become an architect. But recently study has taken backseat to more exciting pursuits. It started a few weeks back. I share a student apartment with a guy and we pretty well lived and studied independently. He was majoring in history and we didn't really cross paths much. I'd been dating a girl and she'd stay over now and again. It was fun but college work was taking up more of our time and the relationship had finished. As you might expect it became more difficult to satisfy my natural urges and I just buried myself in my studies even more. That was all about to change.
My flatmate had been invited to a fancy dress do. I'd been invited too but had decided to do some work and to tidy up for my parents' visit next day. Earlier that day he'd asked me quite casually if I'd help him out. He'd decided imaginatively to go dressed as a girl and had left it all to the last minute and unsurprisingly found himself short of some things. Could I help? My ex-girlfriend had left some everyday small items behind, bras, panties, pantyhose and the like. He asked if he could take them and since I was about to chuck them anyway I handed them over. I did smile when I thought of him trying to get into girls' underwear.A little later he appeared wearing some things, panties, bra, pantyhose and a top of some kind. At first the sight of him like that looked weird.
Well?' he asked. Do I pass?'
I raised my eyebrows, and nodded unconvincingly. Much like his attempt actually. Not in any way perturbed by my lack of enthusiasm he said
`Hell, with a wig, skirt, heels and fake boobs, I'd pass. Maybe I'll get lucky', obviously enjoying his new found femininity!
He disappeared into his room and a little later appeared donning a blonde wig. He's beginning to look quite cute. I'm also becoming aware that something's happening with me. I'm thinking how good his legs look in the pantyhose. He must intuit something, perhaps noticing my furtive glances.
`I hope the skirt holds me in a bit' he says.
I smile. But something has changed.
`These pantyhose feel great. Good for toning'.
I'm feeling quite strange now. Sensing this he moves closer.
`Here have a feel'. He's smiling. 'What? No way' my tone trying to indicate shock.
He doesn't move, just showing surprise then impatience. I run my hand quickly over his thigh.
`Yeah, they feel good, silky. You make an attractive woman' I say. 'You're a shy one. I know what's going on in your mind', he smiled again, 'and in your trousers'.
Before I know it we're necking and kissing playfully. He guides my hand over his legs and then to his crotch. He pushes his tongue deep into my mouth as I massage his bulge and feel it respond. I'm surprised how sexy that is. His hand has by then unzipped me and probing inside my shorts as our kissing becomes more urgent. I feel his cold hand grasp my stiff cock. I gasp and he makes a similar sound as I push my hand under the band of the pantyhose and into his panties. Mmm he feels so hard and warm. As we rub each other's manhoods, he whispers into my ear.
`I don't think I'm going to make this party. All this effort I've gone to'.
He smiles as he says this. Still we gently massage each other.
`Your bed or mine?' he whispers softly. I stiffen even more at the suggestion and he responds by more passionate kissing.
Then I'm guiding him to my room.
`Pantyhose on or off?' he asks.
`On!' I say assertively.
He smiles and sits on the edge of my bed. Unbuttoning my shorts his mouth searches out my hardness that's pleading for relief...
It's now quiet and dark. The curtains waft gently from the cool wind and the open bedroom window. I'm quite awake. I'm not sure of my mood. I hear the gentle rhythms of his breathing beside me. It's sinking in slowly what has happened. I have to admit I enjoyed it. My orgasm was powerful. And so was his if his noises of pleasure and the quantity of his cum is anything to go by! But now in the dark I'm not sure if I want this. He stirs perhaps sensing I'm awake. He turns towards me and I feel his hand on my thigh. It rests there a while. And then it moves to my cock, dormant now. But on first touch it responds. He moves closer to me. I move my hand toward him almost unconsciously. His cock is erect and in the dark that gives me a thrill. We're kissing. My uncertainties seem to vanish in the melee of stroking and kissing in the dark. God, I want to fuck him. I say it to him. He responds with a low moan and then a `yeh, I want you to fuck me'. Our lovemaking earlier had been oral, exciting but not primal. Now it seemed we needed to go to the next level of intimacy. Of course I felt completely out of my depth. I imagined that he was already experienced and that was confirmed when he said he had lube in his room. He asked if I had condoms. I did. While he was away I put on my bedlight and searched the drawer for the condoms. I was excited and anxious. I found them and removed a few, then switched off the light so the room returned to darkness. My erection had diminished but when he got back into bed we continued our loveplay which again restored my lust. He sucked me for a while and I was anxious I'd come too quickly but he was preparing me for the condom. He squeezed some lube onto my fingers and told me to lube him up. Guiding my hand to his hole and whispering instructions part instructional part unprintable I applied him tenderly. I asked how he wanted me. He wanted to know what would get me hot. I wanted him under me like a girl.
`That's how I like it, big boy' he cooed.
It was dark in the room. We were just shapes and shadows to each other's eyes. But our other senses were acute and fired up. He guided me, encouraged me, nibbled my neck, wrapped his legs around me as I sought out his hole with my cock. I pressed against him. I thought that I'd never be able to do it. I worried I'd lose my erection but his kissing and his words and his moans kept me solid. And then I was in and he gasped and so did I. Oh, it felt so good, so tight but hot and enveloping. I held position for some moments and then moved rhythmically slowly taking my lead from him. We kissed tenderly. I'd never experienced anything so gentle and intimate. There was no longer the urgency. `Make love to me' he moaned. I felt myself swell inside him. He felt it too because he groaned and pushed against me. I was aware too of him - the position he maintained to accept me inside, his own lust trapped between our tummies. But the urgency was returning. Our rhythm increased, our lust grew. I told him I wasn't far away.
`Come darling, fill me up'.
He was bucking now which was sending me wild. I felt him thrust, he gasped and tightened around me and then I felt the wet and warmth between us. He was cumming profusely and noisily. I needed no further inducement and I was there. Oh God! I felt like I was emptying my body. I don't know what sounds I made. I felt like an animal - a ravenous wolf. He held me tightly as my rhythms slowed, nuzzling my neck and face. I felt myself slip out of him and both of us relax. I moved onto my back exhausted.
When I awoke it was light. He wasn't there. I looked at the clock it was 7. I heard some sounds from the kitchen and sure enough he appeared with coffee. We said nothing just drank coffee and relaxed lazily.
Your parents are coming when?' he asked after a while. Midday, I think. Time enough to clear up.'
And I thought `and time enough for more fun in bed!.
He bends to pick up something from the floor. He's smiling and holding the pantyhose that started all of this.
And what will they make of these?' he asks. I'll just have to say they're my girlfriend's.' I reply.
We both laugh. Then he starts to slip them on while he smiles over to me. I get stiff immediately. He stands up and faces me. Mmm he's up and ready too.
Tidying up is going to have to wait a bit longer' he says, rubbing his bulge seductively. And I think we're going to make a lot more mess before then.' he says cheekily.
I know exactly what he means and smile at him lasciviously.