Tranny Tales...
I am a single male in my late 20's that gets his kicks by dressing up like slutty whore and entertaining discriminating gentlemen. Together with my partner we have a thriving little service going and it keeps us in nice clothes, jewelry and the latest high heels.
This all started in a rather unusual way about ten years ago...
I was 17 years old when my dad accepted a position overseas, expecting us all to go along with him, but being a senior in high school I wanted to finish school here and didn't want to go, plus I had another problem...I am bisexual and this country in the middle east where dad was going, lets just say, frowned upon such behavior.
The solution we agreed upon was for me to stay with my dads step brother, Ron. I always liked Ron He was much younger than my dad, only about seven years older than me, and was on the swim team in his day like I am now, and was always friendly and easy going.
Mom and Dad moved me in with Ron and took off for the
That first night Ron and I had a few beers and cooked some burgers on the grill and got acquainted. I saw that Ron was deep in thought and seemed like he had something to say but when I asked him what he was thinking he shrugged it off and said we can talk about it later, and assumed it was some house rule or something so I didn't think anything of it at the time.
Well, a week or so later I went off to swim practice on a Saturday morning telling Ron that after practice some of us guys were hanging out and I wouldn't be home until later that night. When I got to the pool it was closed for maintenance and only one teammate was still there. Billy and I went to his house and got high and drank a few beers and that got me pretty horny so I headed back home with good old masturbation on my mind.
I walked into the kitchen and I was shocked to see a gorgeous and sexy babe sitting at the kitchen table polishing her nails! My first thought was Ron, you dog! I said hello there and this sexy thing just looked at me and smiled.
Wait, Ron, is that you?
Yes...what do you think of Veronica?
Holy shit was all I could manage to say as I moved closer for a better look.
Ron, err Veronica was about the sexiest thing I had ever seen in person.
She had on a red, black, and gold wrap dress showing some nice cleavage, tan stockings with a black garter peeking thru and gold high heel strappy sandals, matching bracelet and earrings, and a long wavy highlighted blonde wig. Her make up was bold and dramatic with eyes outlined in black and long lashes and perfectly outlined red lipstick,
and she was painting her long nails a matching red.
I didn't know what to say but I knew one thing, Veronica was HOT! I was just staring at her as she explained she was a crossdresser, has been since her early teens and that I was just going to have to get used to it if I was going to live there. She looked up from her nail painting after having said that and asked if I was OK with that? I stammered a yes and saw her beautiful eyes linger for a second at my crotch area.
Judging by that big hard boner of yours I guess you like?
Um, yes, I mean, ah, um,...I stammered.
Pour us a drink Bradley; I want vodka on the rocks, she said.
I poured us each one while Veronica finished her nails then I followed her to the couch in the family room, watching her beautiful little ass wiggle and her long shapely legs the whole time.
Veronica encouraged me to ask any questions that I had and I had a million of them.
She explained that dressing up makes her feel sexy and attractive as well as relaxed and confident and she likes to dress every chance she gets. She said she "adores" sucking cock and even likes getting it up her ass on occasion, and has several boyfriends and other crossdressers she meets on the internet and thru a club she belongs to.
As we sat there that Saturday afternoon and got loaded together I admitted to him, um, her, that I was bi and actually thought about crossdressing briefly a few times and now with her help I might want to actually try it sometime. Veronica thought I would make a great looking girl with my full lips and long lashes and said she would love to help me out when I was ready.
By this time we were sitting next to each other on the couch and we were pretty relaxed by the vodka. Veronica began stroking my long hair at the back of my neck as we talked, and my dick was rock hard and straining in my jeans. Nervously I started to talk about the swim team and Veronica took her other hand and with her forefinger ran her long red nail slowly and deliberately over the bulge in my jeans from base to tip.
If we do well in our next meet we have a good shot at the state finals, I said.
Is that right she said, not looking up.
And I think we will do well, everyone seems to be swimming real good right now.
I want to suck your big hard cock Brad, take those jeans off.
I immediately stood up and dropped my jeans as Veronica took her lipstick from her purse and applied another creamy coat just inches from my cock.
She cupped my balls in one hand and wrapped her hand around the base of my dick with the other and kissed the tip, leaving a red lip print.
That's sexy isn't it, she purred.
Gawd I `m going to cum I think.
Anytime you're ready Brad.
class=Section2>I looked down as her sexy red lips slowly engulfed my cock. Her long black lashes fluttered as she took me all the way in her mouth then, just as slowly all the way out. It was nothing like the quickie blowjobs I've had before and I felt myself starting to cum.
I glanced down to her dress which was pulled up exposing her panties, garter and stockings and my eyes followed down her long legs to her sexy heels and ankle bracelet, then back to those red lips sucking me. I exploded into her mouth and she responded by taking me deep in her throat. I never felt anything like that before. I shot several spurts down her tight and warm throat then she withdrew her mouth and squeezed out one last spurt of cum onto her lips which she licked off with her tongue, the she looked up and smiled at me.
I fell back the couch trying to catch my breath and Veronica lit a cigarette and reapplied her lipstick and sat back on the couch smiling.
Guess you liked that, huh?
That was the best blow job I have ever had Ron, er... Veronica.
Veronica and I talked some more and she explained that she often dressed around the house and hoped I didn't mind, but if I did too damn bad, and that on the weekends mostly she dates guys or sometimes parties with other crossdressers. Of course I didn't mind and again said I may be interested in dressing up too. She agreed that might be fun but of course my parents were to know nothing about this. (duh!)
My head was spinning, not only from the alcohol but taking all this in and sitting there talking to just about the hottest babe in the world. Veronica was so sexy that I forgot completely that this was my Uncle Ron, and it wasn't long before I felt my cock growing again. Veronica reached over and nonchalantly stroked me as we talked. I laid my head back and closed my eyes as she expertly gave me a teasing hand job then I felt her lean over and kiss me on my lips. The taste and smell of her lipstick and perfume sent me over the edge and I reached between her legs and felt her cock which was tucked under in her panties. As we kissed I felt her lipstick smeared all over my mouth, something I don't think I will ever forget and I tried to get her cock out from the tight panties.
Hold on Brad, she said, then lifted her ass from the couch and slipped her panties off. I reached for her cock and it was long, thin and hard. It was my turn now to reciprocate and I leaned my head down in her lap and took her cock between my lips. I've sucked cock before a few times but never a shaved cock and balls smelling of Chanel No. 5 and legs adorned in sheer stockings.
Veronica softly moaned as I sucked her and it took awhile but I felt it twitch and grow then begin to spasm and shoot. She tasted somehow feminine and musky and I eagerly swallowed all I could. Veronica then lifted my head up and we kissed. She inserted her tongue in my mouth and we taster her cum together.