It's kinda long, but I hope it's still good:
In all honesty, it was just alittle bit of fun between friends that got a little carried away. But, boy, was it a good time!
I was hanging out with my friend Tina. She's been my best friend since junior high. As beautiful as she is, we've never crossed that line from friends to lovers, or even to casual fuck buddies. Tina's in her early 30s, slender, with dark hair and green eyes. A great set of boobs and a firm ass make her one of the best looking women in town. Throw in the fact that seh's an insatiable cock junkie, and her popularity goes through the roof.
Anyway, we were watching a documentary on TV about crossdressers. They talked about how some guys get sexual pleasure out of wearing women's clothes, and how, for some women, it's a sexual turn-on to see men dressed as women.
After teh show was over, Tina and I started talking about it. Neither
of us had ever tried it. I'd never worn women's clothes or makeup, and
she'd never actually seen a crossdresser up close. The decision was
made to dress me up in some of her clothes complete with makeup and a
wig, and see how I looked.
We went to her bedroom, where I stripped as she pulled out
some clothes that she thought might fit. I'm a smallish guy, and the
difference in size between us is pretty slim, so she didn't have much
difficulty. SHe got her first ever look at my 7 inches, smiling and
saying, "Not bad, bud." I first put on a pair of lacy black bikini
panties. They were pretty snug, constricting my package a little more
than I would have liked. Tina assured me I'd be fine, adding that the
tightness would probably help keep my dick in place, meaning mostly
unnoticeable. I put a pair of thigh-high fishnet stockings and a black
bra, which we stuffed with socks, giving me a bust about 34D. I
shimmined into a knne-length black skirt, tight at the ass and loose
around the knees. I pulled a long-sleeved white turtleneck over my
head, and stepped into a pair of black cowboy boots. Tina fit te
shoulder-length blonde wig onto my head, and set about applying the
makepu. A little eye liner, some mascara, light blue eye shadow, a
dusting of rouge, and pink lipstick, and she was done. Eyeing myself in
the mirror, I thought, "I'm not the hottest chick around, but not bad.
Hell, if I wasn't me, I'd fuck me in the ass." "You don't look
half-bad," Tina said. "Thanks." We headed back downstairs, where we
played around for a while, Tina teaching me how to sit like a lady,
walk like a lady, and drink like a lady. We were having a good ol'
time, just the two of us, when the doorbell chimed. Tina loked at me,
"Just sit still, and don't say a word." Tina opened the door to two
guys, roughly in their mid 20s. Both were holding a bottle of beer. One
was muscular and blonde, with a hint of a goatee. The other was
smaller, a little chubby, with dark hair and a baby face. "Hey," said
the blonde. "Sup?" "Nothing, Tommy," Tina answered. "What are you up
to?" "Well, I thought I'd come over and see if you wanted to play a
little," he eyeballed me at this point, "but it looks like you already
got company." He took a swig. "That's too bad, 'cuz I was really
horny." "Oh," said Tina. She turned to look at me and I caught a
glimpse of impish playfulness in her eyes. "You know," she purred,
"just because Dawn and Rob are here, doesn't mean nothing can happen.
In fact, you haven't had your cock sucked until you've had it sucked by
Dawn." I was shocked! What was she saying? I'm not gay! She rubbed
Tom's cock through his jeans. "Sit down for a bit. We'll have some fun
yet." She led him over to the recliner, unzipping him as they went.
"You too, Rob." Like an eager puppy, ROb followed. Tom sat down as Tina
pulled his pants and underwear down, his dick already showing signs of
life. It was bigger than mine, about 9 inches, and fat like a kielbasa.
Tina looked at me. "I'll warm him up, the rest is up to you." I watched
as she slowly stroked his cock with her finernails from the base up to
the tip. It stiffened a bit as she did. Then she put her tongue to it.
SLowly she swirled her tongue around the crown, then sucked the whole
thing in all at once. Tom's dick stood at attention as Tina worked her
mouth up and down on it. She coated it with a nice layer of saliva,
pulling it out of her mouth. Continuing to pump it, she said to me,
"Your turn." Feeling like I had no choice, yet oddly turned on, I got
down on my knees next to Tina. She whiespered, "Just do to him what you
like done to you." Then she stood, leaving me on my knees with Tom's
cock staring me in the face. I grabbed it, feeling another man's pole
for the first time in my life. I did as she had, stroking it up and
down a few times before I got the nerves to touch my tongue to it. That
wasn't bad, I though, but how'm I gonna get this thing in my mouth? I
sampled the crown, taking the first inch and a half in. That was okay.
I tried a little more. Pretty good, actually. I was starting to enjoy
myself. I continued pumping with my right hand as I reached up with my
left, cupping his balls in my hand. With each bob of my head, I took a
little more shaft in. Finally, I managed to bury my nose in his pubes,
avoiding,
miraculously, my gag reflex. It seemed to be working, judging by his
moans, so I kept at it. Bob head, stroke shaft, massage balls. Repeat.
Behind me, I heard Tina say, "You knoe, Rob, Dawn loves getting it from
both ends. You wanna fuck that as?" "Hell yeah!" he excalimed. I felt
my skirt being lifted, then the panties being pulled down. Tina
whispered in my ear, "Just keep your legs together." I felt something
cool and slick on my asshole, then what felt like a finger inserted.
Then another. Then they were gone. "Go ahead, Robby, all yours." I was
enjoying sucking Tom's cock so much, I figured I'd just let Rob do his
thing. I ddn't figure he'd get it in my virgin ass anyway. I was wrong.
I felt a little pressure, then a lot of pressure, on my sphincter. Rob
grunted, then I felt a little pop as his head made it in. I kept
working Tom's pole as Rob slid all the way in. I felt his balls slap
against my thighs. "Oh man! That's tight!" Rob said. There I was,
dressed i women's clothes, a dick in my mouth and another in my ass,
and having the time of my life. My own cock was rock hard now,
throbbing in time to Rob's thrusts. I tasted something salty and felt
Tom's dick throb a bit. It took a second to realize he was cumming, and
by then it was too late to move. He erupted in my mouth, sending hot
ropes of cum right down my throat. It coated as it went, but tasted
good. I wanted more, so I feverishly went to town on him, sucking
harder and harder, slurping every delicious drop I could. Moments
later, I felt Rob explode in my ass, convulsing as he muttered, "Fuck!
Fuck! Fuck!" He went limp, and his fluids started leaking out of my
ass. Rob pulled his half-erect dick out of my mouth and stood up,
knocking me onto my side. "Well," he said, "That was fun. Let's go,
Rob." They both pulled up their pants, gave me an approving glance, and
headed out the front door. As soon as the door closed, Tina said, "That
was the hottest thing I've ever seen!" She pulled me up to my feet,
then pushed me back int the recliner. My skirt was still bunched up
around my waist, my throbbing boner sticking up like a soldier at
attention. Tina stripped out of her clothes in one sweeping gesture,
threw a leg over each arm of the chair, and slid her dripping wet pussy
onto my dick. I buried my face in her bouncing tits as she pogo-sticked
on my pole. It seemed like seconds later when I said, "I'm cumming!"
"Not in there, you're not!" she gasped, pulling herself upwards off me.
She reached down and pointed my cock at her ass. She rode me hard all
the way down jsut as my cum started shooting out. I filled her with
what felt like 40 gallons of sperm before she exploded in her own
violent orgasm. As the fluids ran down my cock and balls and pooled
under my ass, Tina asked, "Wanna do this again next weekend?"
"Absolutely," I answered. "Absolutely."
littlej1019
The Masturbation page
The Masturbation page
Leave a comment