My Girlfriend’s a Guy, Shemale Sex Stories

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.