I have a great career and all but I spend all week just trying to get through the week so on the weekends I can indulge my true passion...dressing up in a tight skirt, sexy blouse, high heels and stockings and sexy make-up, and sucking a big hard cock and/or getting my bottom nailed. I am a tranny gurl.
I've been crossdressing off and on since I was 13 and gave my first blow job to a much older guy when I was 16 dressed as a little slutty tart in a public park. I can't describe the feeling when I dress up but it's amazing. I feel stress free and happy with a heightened sexuality and confidence that I never ever feel as a guy. Plus I feel very fortunate that I have the great privilege to experience life as both a guy and a girl. It is so damn cool!
I am single, 26, and I can pass easily as a guy or a girl. (I am 5'7" tall and weigh about 136 lbs with full lips, long lashes, blonde hair and blue eyes) A few friends know about my little "hobby" as I call it as well as my parents and sister and they deal with in their own way I suppose.
I party with all sorts of people that I meet in various ways. I meet guys and occasionally couples through web sites on the internet, sometimes I pick up guys at bars, and also thru friends in the lifestyle. I also cruse the ABS (Adult Book/Video Stores) sometimes when I am looking for a quickie, and I even will take a client or two from an escort service on occasion, just for kicks. You would be surprised at how many guys who consider themselves totally straight that love getting oral sex from another guy in high heels and panties and lipstick!
I have a huge collection of sexy clothes, lingerie and high heels that I have built up over the years and lots of make up that I adore playing with, and have become very good at dressing and acting 100% female. Anything and everything ultra feminine and sexy are my fetishes so naturally I have over 50 pair of high heels and I suppose over a hundred lipsticks, not to mention a few dozen skirts, blouses, dresses and about 30 bras, lots of stockings in different textures and colors, lots of lingerie and a nice assortment of dildos and vibrators too, lol.
I guess by some standard I am a sex addict and I sometimes party too much, but I do my best to balance my compulsions and not let it interfere with my career or family, except on weekends-that's Rexie time.
Anyway...the reason for writing is to hopefully excite and arouse you by relating some of my more entertaining experiences, and I have had my share of those! I have had quickie blow jobs in the hallway of and ABS, turned a trick or two or maybe more in a very expensive hotel room, been the centerpiece of a gang bang- more than once, sucked off a clueless groom at a bachelor party, been with white guys, black guys, Arab guys (they LOVE American trannies!) and several couples, and I been to some bizarre sex parties, even sometimes bizarre to me and I am unshockable.
I suppose I can start by telling you about last weekend...
Because I was meeting a new guy, I left work early, around 2:30 and stopped by Macys to see the new Chanel make up colors and left with a sexy red lipstick, mascara, and eyeshadow. Expensive, but I love Chanel cosmetics! The experienced girls at the counter are used to guys buying make up for themselves and I quit feeling funny about that a long time ago. This girl even smiled and said to have fun as I left. Plus, buying make up still gives me a thrill not to mention a hard-on, lol.
Once home I took off my yucky guy clothes and put on a black silk robe and high heels and made myself a martini as I went thru the mail. The martini and the robe and heels helped me relax and get into the mood for my date. I met Lawrence on line several weeks ago. He is a hunk of an Afro-American guy and very sweet. He is cute, wears glasses and is married and seems infatuated with me but has never been with a tranny before. We started talking in a chatroom then we exchanged pictures (he told me he has a 9" cock!) and then we had a few phone calls before deciding to meet. We agreed to meet at a club first then take it from there.
As I was relaxing I got a call from the service that one of my regulars was in town and asking me if I was interested for 7:30. This guy is a sweetie-pie. He is a high powered banker or something in his late 60's and all he ever wants is a blow job He doesn't last long, treats me nice and tips very well. I agreed to meet with him but it had to be at 7:00 because I had my date with Lawrence set for 8 and after a phone call the service agreed.
I took along hot shower, shaved my legs and painted my nails (I keep them long) and toes a shade that matched my new lipstick and sipped my martini before I started my make up. As I said, I love make-up and enjoy taking my time and always strive for perfection. I laid out my make up on the counter including my new Channel I bought and carefully began my transformation to Rexie, (my gurlie name). Make up gets my motor running and is a big part of changing my whole personality when I dress so I like to take my time and enjoy every second of it.
First I applied my foundation with a make up sponge to my face, neck and chest then a light dusting of powder to set it. My new Chanel eye shadow in a light smoky brown was next then a darker brown in the crease of my eyes and then gold under my brow. I drew in my brows with a seductive arch with a brown pencil then lined my eyes with a soft black and lightly smudged it in, then applied a liquid liner to my eyelid. I put on a great pair of long false lashes then sipped my martini and had a cigarette as the glue on my lashed dried. (I only smoke when dressed and its always white, thin 120's). Next about 10 coats of mascara to both my top and bottom lashes and my eyes are ready to go and they looked amazing. I applied some pink blush to my cheeks but I always save doing my lipstick until I get dressed for several reasons not the least is which I have a major lipstick fetish and I just prefer it that way.
I put on a sexy black bra and filled in the 36D cups with silicone breast forms. They are expensive but nothing is better that having the realistic feel and look of breast forms that warm to my body temperature, and with the right bra and these titties I get a nice cleavage effect too. Next I put on a black panty gaff that holds my tucked under penis nicely giving me a perfectly feminine crotch, then black thigh high stockings with elastic lace at the top so they stay up and a leopard print stretch skirt hemmed just above my knee and a black cardigan blouse with an upright collar and plunging neckline. I admired myself in the mirror and was reminded how lucky I was to have such a feminine body that I can hide when dressed as a guy and exploit when I dress as a girl!
I put on a new wig I got just a few weeks ago that I absolutely adore. It's long and wavy and full and a blonde color with brown, gold and red highlights that cascades over my shoulders, and it's so easy to take it out of its box and style. I put on a sexy pair of dangly gold and black earrings and a gold necklace and bracelet just when the phone rang. It was Lawrence calling just to tell me how excited he was to see me. I told him I was getting ready and he asked me what I was wearing for him. After I described it to him he just sighed and said he had a hard on just talking to me so I told him to hold that thought and that I would see him soon. He is so sweet!
It was difficult choosing my high heels and I tried on several, deciding on a pair of black platform sandals with an ankle strap that allowed my red toenails to show-I think that's so sexy. My cock was straining to grow it its tucked position also reminding me that after thousands of times I have dressed it still and always will get me excited by doing so. (If you haven't tried it, you really should. It's great fun.)
At last, my favorite part of dressing up...lipstick. I lined my full lips just slightly outside my natural lip line with a brick red pencil, changing the shape slightly to a more feminine outline then I screwed out my new Chanel lipstick and admired it before filling in my liner. Fuck, did it look and feel amazing on my lips. Again I thought about how fortunate I was to be able to dress and look like such a hot and sexy babe. There is nothing like it! I sprayed some No.5 in all the right spots, threw some make up, perfume, lube and a few condoms in my purse then went into the kitchen to finish my martini and have another cigarette.
At around 6:45, and sufficiently buzzed and excited about my evening I took one last look in the mirror, applied another coat of mascara and lipstick and headed out the door for the short drive to the hotel where Mr. "X" was staying. It's a hoot dressed like this and driving in the daylight. I get lots of double takes, waves and horn beeps but I've learned to ignore them. I've been followed a few times when I respond to them so its just best to pay no attention, but it is certainly a nice ego boost, lol.
I pulled into the hotel parking lot and it was full so I decided on valet parking. This hotel is very high end and expensive and loaded with security but they look the other way when a guest had a visitor so I confidently strode thru the lobby, heels clicking on the marble floors and stares from the other patrons aside, I got into the elevator, thankfully alone. At exactly 7:02 I knocked on the door and was greeted immediately by Mr. "X", dressed in suit pants and white shirt and tie and a scotch in his hand. He is a great looking guy for his late 60's, tall, thin, silver hair, sexy blue eyes and he greeted me with a big smile a hug a pat on my ass and a kiss on the cheek. We have been seeing each other about every other month or so for maybe a year so we had the routine down pat. He poured me a vodka rocks and we talked a while on couch, and he already had the going rate laid on the table. After some sexy talk and massaging him thru his pants he stood up and I undid his belt, unzipped him and dropped his pants to the floor then pulled down his boxers and he stepped out of them and sat on the edge of the bed. I knelt down between his spread legs and took his semi hard cock into my hands and kissed it several times, leaving red lip prints all over it as he grew in size. He is not long but big around and soon he was between my lips and I was sucking away. He started calling me his little whore and talking dirty to me which I knew was how he got off and in just a few minutes he moaned loudly and spurt into my mouth. I continued until he finished, swallowing all of his milky juices then I leaned back as he sat up and smiled at me, thanked me. I went into the bathroom, rinsed out my mouth, redid my lipstick (an expert cocksucker can give a great blow job without messing up her lipstick, lol) and on the way out Mr. "X" handed me a generous tip, (paying for my new make-up I thought!)
I rode down the elevator with three semi-drunken guys that made silly passes at me and as always I got a kick knowing that if they only knew they are ga-ga over a girl with a cock. Guys are so easily impressed by sexy women, but that's a good thing.
I drove over the club where Lawrence and I agreed to meet and got there fashionably late, around 8:20. This is a mixed club, both gay and straight with a few transsexuals and crossdressers scattered about and both a black and white cliental. I used to come her often but it's been a while and at this time it was not very crowed yet. I looked around, got lots of stares from the guys and a few lesbians as usual and didn't see Lawrence. It's pretty common to be stood up by someone you meet on line, but since he called earlier I was pretty sure he would be there. I went to the bathroom and took a pee then checked my make-up then spotted Lawrence sitting at a table over in the corner.
I said hi and he jumped up and awkwardly started to shake my hand so I wrapped my arms around him and hugged him, making him laugh. He was nervous as first timers can be sometimes but I did my best to put him at ease and we ordered drinks and talked. He told me how beautiful I looked, several times, and soon had his hand on my knee as we talked and after the second drink his hand was under my skirt at my stocking tops and I didn't object. He definitely was fuckable in my opinion. He is about 6'3' tall, maybe 230 lbs with shaved head, trim waist and big, big hands. He is very dark but has thin lips and a perpetual sexy smile on his face and after he relaxed he was very easy to talk to. He excused himself to go to the bathroom and when he returned I couldn't help but notice the sizable outline in his tight pants. When he sat down, this time closer to me, I put my hand on his cock outline ad asked if this was for me? He laughed loudly and replied that yes it sure was if I wanted it.
Since we were in the corner and it was a dark corner at that, I unzipped his pants and fumbled for his cock, finally getting it out and I wrapped my had around it and just held it. I told him he is even bigger than advertised and he said he didn't want to scare me away. I've been with a few big ones before but Lawrence was huge in my little hand. I am not a size queen and prefer average size but this cock on this body was a real treat for me and it really turned me on, a lot.
Only problem was he didn't have a place we could be together since he was married and I rarely entertained at my place. We decided to get a room at the Holiday Inn close by so I reluctantly let go of his cock and he tried to stuff it back in his pants. If anyone was watching, and I am sure some were, it was obvious what he was doing! After he finally tucked it in, he paid our tab and we took his car down the street to the hotel.
I sat next to him as he drove and massaged his cock thru his pants and with a huge boner he went in and got us a room. I laughed when he returned with the obvious boner still straining away and we pulled up to the room around back and went inside. He immediately grabbed me once inside and we kissed passionately as I fumbled with his belt and zipper as he squeezed my ass with his big hands. I then pulled away and told him to undress and that I would be back in a second and I headed for the bathroom.
I took off my skirt and blouse and redid my lipstick of course then opened the door to find him lying on his back in bed, arms outstretched, totally naked and his cock rock hard and laying over his stomach. In my bra, panties, stocking and high heels I knelt down near his cock and with both hands pointed it up to my mouth and took it in. It was weird having this monster in my mouth. My jaw was stretched wide open and I could only get past the head of his cock, leaving enough of his shaft to wrap both hands around it. As I sucked and jerked him he was rubbing my cock tucked under me and feeling up my ass. He tried to get into my panty gaff but they are pretty tight, in order to hide away my cock so after several attempts I had to stop and stand up to take them off. My clitty-cock was hard and pointing straight out when I got back in bed and resumed where I left off. He stroked my cock several times and I could tell he liked doing so from his soft moans. Some guys don't like to know I really have a cock but Lawrence apparently did. As I worked on his cock his hand found my little she pussy and I saw him get his finger wet with saliva and he massaged my hole then slipped a finger inside. This as always made me kick it up a notch and soon I was moving up and down, fucking his finger as I sucked him. After a good long while he asked if he could fuck my ass, but the thought frightened me. I moved up to kiss him as he continued fucking me with his finger and I whispered we can try it but it has to be my way. He quickly agreed and I kissed him and said be right back.
I went to my purse and grabbed the lube but first I put on another coat of lipstick without even looking in the mirror and get in bed next to him. I put some lube on his finger and he slipped it back inside my hungry ass as I generously coated his cock and rubbed it in. I then got on top of him and straddled him with my legs on either side of him, and I reached behind me and guided his cock to my hole. Once at the opening I pushed out my sphincter for him and slowly pushed back as he pushed forward. I strained a little and I felt a little flash of pain then it slid in, maybe an inch or so and Lawrence and I both moaned in unison. I told him to hold still for a few seconds until I got used to it, than I started slowly moving back and forth on his cock.
He asked if I was OK and I smiled and kissed his neck and asked the same of him. He said he said it felt amazing and I had to agree. We continued fucking like this until I was able to get maybe three or four inches inside me. I never felt anything like this before and we continued like this in unison for some time. I felt myself on the edge of orgasm when he stiffened and seemed to stop breathing as he fired his cum up my ass. First one spurt, then another, then another splashed inside me. As he did so I continued moving back and forth impaled on his cock, whispering yes baby fill me with your cum. Just as he squirted his last load I felt my own orgasm let go and with my cock rubbing against him I shot my cum onto his stomach and chest.
I kissed him and rolled off next to him and we laid there, our hearts pounding only saying an occasional `oh shit' for the next several minutes, lol. I cuddled up next to him and massaged my cum into his hairy chest, feeling so small and feminine in his big strong arms.
In time and on still wobbly legs we got dressed and I did my best with my make up then he drove me back to my car. We talked a while in the parking lot agreeing to get together again soon. Then we kissed good-by and I made it to my car and drove home, a bit dazed and confused and leaking my new lovers cum from my slightly sore little ass.
Well, that's it for now folks, but just say the word if you want to hear more... XXOO Rexie:)