After a long absence from crossdressing I just got back into it in a big way and I've had some very erotic experiences I thought I would share and I hope you enjoy..
I began my fascination with all things feminine and sexy early by raiding my moms and sisters drawers to wear their sexy undies when I was maybe nine or ten and by 13 I had progressed to dressing from head to toe in their wigs, sexy skirts, hose, high heels and make-up whenever I was alone. I loved the feelings I had when I dressed and starting at puberty fantasized about sex with boys. I definitely liked girls and maybe I dressed because I admired and envied them so much, I don't know. I am not gay, but bi and only when I'm all dressed up in a sexy way.
I went off to college in my late teens and dated a lot of girls and had my fair share of sex. Since there were few opportunities to play dress-up during those years, and with regular sex with girls I lost most of my interest in crossdressing. I had the urge every once and a while but managed to suppress it as best I could. Next thing I knew I got married and began a career so I assumed that crossdressing was just something I did in adolescence. However, after eight years of marriage both my ex and I realized that our marriage probably wasn't a good idea and with all the pressures I had at work I started to feel those old compulsions again to dress up like a slutty whore again to let off some steam. I always felt very sexy and highly aroused yet strangely relaxed comfortable when I dressed and I began to miss it a lot. I started again to often fantasize about dressing real sexy and giving a big strong man a blow job or even getting my `pussy' fucked.
Once we split up and I got my own place, the floodgates opened! I spent a ton of money on sexy bras, panties, mini skirts, high heels, make-up, jewelry, and wigs and started dressing up every chance I had which was most evenings and every weekend and was in absolute heaven. I hit the internet (my fem name became Rexy Ann Monroe) and in no time I had several promising contacts with guys and other crossdressers. For the first few weeks I flirted with everyone and on line and soon got a web cam and did some cam shows and exchanged photos with several interesting people. I took my time getting made-up and dressed enjoying the process immensely. As I worked on perfecting my look (the sexy, slutty, look of course), I would have a cocktail or two (or three) and play online teasing all the horny boys (and gurls) out there, fantasizing about sex with them the whole time!
I narrowed my search down to a few special guys and other CDs that I was attracted to and with my self confidence growing and inhibitions released by my vodka or the rocks, I made my very first date. His name is Lawrence and he is a great looking black man. (Seems several of us gurls find black guys sexy and many black guys seem to be attracted to shemales too.) Lawrence is single (divorced) and is 6-4 and maybe 225 lbs with a great athletic body and a sweet personality. He seemed very smitten with me and we had several long sexy talks on the phone that progressed to sexy and sometimes nasty phone sex. He lives about an hour away but works on this side of town so I invited him over on Friday after work.
Needless to say I was a nervous wreck all that week. Nervous and excited at the same time with butterflies in my stomach but extremely horny and sooo excited to get his cock between my red lipsticked lips! It seemed like Friday would never come! Finally the day arrived and I took the day off to get ready for the big event. I got up the nerve to make an appointment with a local nail salon to get nail tips put on so I would have sexy long nails for my lover boy. Fortunately there was no one else in the salon when I got there but to be honest I was so horny and motivated I didn't really care much. The Asian lady that owned the salon didn't even flinch when I told her what I wanted and she gave me a beautiful set of long sexy nails that we painted both agreed to pain in a hot red color and I even bought the polish in case I needed a touch up. She suggested she paint my toes also and I totally agreed! (I quickly learned that having long nails makes everything harder to do with your hands, but I learned how to walk in 5" high heels so I knew I would adapt easily enough and besides.they look sooo fuckin sexy!)
In my lusty conversations with Lawrence I knew exactly what he liked so I tailored my choice of clothing and make-up to his wishes. I laid out my outfit and make-up on the bed: a sexy red bra and panties, black stockings with a seam up the back, a black leather mini skirt, red silk long sleeved blouse with a spread collar, red high heels with an ankle strap and a hot looking shoulder length curly blonde wig. For jewelry I picked a pair of long silver heart earrings, matching necklace and a set of three silver bracelets. I had a raging hard on just setting out my outfit and I debated whether I should relieve my tension a bit but decided to work with it and kept my she-clitty untouched.
Instead I poured myself a tall vodka to relax and with plenty of time before I need to begin my transformation I went to my computer to look at the pictures Lawrence sent me. Gawd, I was so excited to be with my man! His cock looked to be an easy 8" and his balls look so big and heavy. I wanted to feel them sooo bad! His cock was surrounded by a nice crop of curly hair and his cock is dark brown like he is with this cute pink tip the last two inches or so and a nice size mushroom head that I was anxious to lick. I just had to stroke myself looking at these pictures and coincidently as I was doing just that, the phone rang. My heart about beat out of my chest when I saw on caller ID that it was Lawrence! I picked up the phone and said hello in my sexiest albeit breathless voice. He asked what I was doing and I couldn't tell him I was teasing my clit while looking at his pictures so I replied a mysterious "oh, nothing really'. Lawrence said he was really looking forward to seeing me and that he's had a boner all day. I laughed and told him that was sweet and I too couldn't wait to see him. He asked if I might like some champagne tonight and I said that would be great but champagne always makes me horny. He laughed and said he would then bring three bottles! We engaged in some nasty little sex talk together then he asked if he should pick up some condoms. Fueled by our nasty conversation in a sexy whisper I told him no, that I wasn't his cum in my hot sweet ass. He hesitated for a second or two then replied with Oh Gawd Rexy, I want you so friggin bad!' Me too baby' was my reply. He said he would see me around 7 and we both hung up.
I was floating on air at this point. I felt dizzy and my hands were shaking with excitement. I've never sucked a cock before much less had a real one in my ass but I've been practicing with my vibrator and dildo and I was more than ready. The trick, I thought, would be to keep from jumping on his bones as soon as he walked in the door!
I finished my vodka and with a nice warm buzz I took a long relaxing bubble bath and shaved my legs, underarms, chest and some of my pubic hair. (Im not very hairy and that helps). Out of the tub I powdered myself (Chanel No5) and trimmed what's left of my pubes so it was nice and short and sexy looking then put on my panties and my bra. I filled my bra with a great pair of D cup silicone titties. They attach with adhesive and quickly warm to my body temperature so they look and feel almost real, not to mention how great I feel in them!
I poured another vodka and relaxed a little, savoring the moment. I feel so lucky to have this strange and mysterious fetish for crossdressing. At times it's a curse but not at this time, that's for sure. I glanced down at my painted toenails, long red fingernails and my bra and panties and felt a little rush run through me. My boner had calmed down some but I can't ever remember ever being this horny before in my life! Just to paint the picture, I am 29 and 5'9" tall and weigh about 150 or so. I'm slim and have long shapely legs and no visible Adams apple so I am lucky that I can pass as a woman pretty well. Instinctively I began feeling up my luscious tits but decided I better get back to the task at hand before I get carried away.
I applied my foundation to my face, neck and chest then a light dusting of face powder to set it. I filled in my brows that I pluck to a nice sexy shape with a brown pencil then outlined my lower eyelids with a soft black pencil and smudged them in. I chose a great soft plumb color eyeshadow then did the crease with a darker plumb and highlighted my eyes with a pinkish white below the brow. The trick is getting both eyes the same but I'm good with make-up (because I love it so much) and they were starting to look real nice and sexy. I have naturally long lashes but I know Lawrence liked my pictures with false lashes and I put on a real long pair on my upper lid. They can be tricky but they went well this time and I batted them in the mirror at myself and decided they were hot looking. I put on the first of many coats of mascara and took another break from the make-up to let them set before the next coat.
I decided another vodka was in order. I was so buzzed and horny by getting made up and with the anticipation of the evening I wasn't feeling the effects of the vodka at all, or so I rationalized. While having my drink I opened my stockings and put them on. Gawd do stocking feel good! Keeping the seams straight is a pain, but Lawrence said he loves seamed stockings, so anything for my man! My red painted toes look so cute in the stockings however it was time for my high heels. It was a struggle buckling the ankle strap with ling nails but after several minutes I managed to get it done. Fuck me!.my legs were looking hot in those heels and stockings!
I admired myself in the mirror some and fetched my mascara and applied several more rich black coats making sure to define every single lash. I previously brushed out and teased my wig so I slipped it on and it only took a minute or two of styling with a hair pick to make it look great. It feels so nice having long hair brush so lightly on my shoulders. I returned to the bathroom and put some nice blush on my cheeks and more on my chest to accent my cleavage. I sprayed my neck, chest and bush between my legs with some Chanel No5 than started my specialty.red creamy lips. I outlined my lips with a soft brick red pencil just slightly outside my natural lip line. I have rather full lips and they look great in lipstick. I made sure I had them perfectly shaped with a well pronounced cupids bow then I filled them in with a liberal coat a fabulous Dior lipstick shade called `Maraschino', very glossy and sexy dark red color.
I lost track of time and glanced at the clock and it was already 6:30, only 30 minutes until lover boy arrived! I wiggled into my leather mini skirt and put on my red blouse making sure my cleavage showed just a tease. I put on my cute heart earrings that I love so much and my bracelets and I was struggling to put on my necklace with long nails when the doorbell rang! My heart was pounding away as I walked to the front door. I took a quick glance in the mirror and whispered `well its showtime Rexy baby" and peeked out the peephole. There was Lawrence, this gorgeous hunk of a man standing at the door looking nervous. It looked like he had something in his arms but I couldn't tell what it was. I took a deep breath and opened the door just a crack.
"Are you ready for me baby' I said thru the crack, not letting him see me just yet, and "More than you can possibly know babygirl" was the reply. I opened the door wide and his reaction was priceless! Lawrence's jaw dropped and he couldn't seem to move or say anything. `Get in here baby, before all the neighbors see us' I said. He was trying to be cool but he tripped slightly walking over the threshold not taking his deep brown eyes off of me. "Gawd damn", I think he said maybe three or four times.
He told me my pictures were incredible but they didn't do me justice at all and I thanked him. I so wanted to hug my new man but his arms were full.
"Is this for me? I asked. And Lawrence handed me a dozen beautiful red roses and a small box with a bow on it. "Oh that's so sweet and I gave him a peck on the corner of his lips, leaving a sexy little red lip print on him. As promised he had three bottles of champagne too so I said lets go into the kitchen. Lawrence set down the champagne bottles on the counter and I put my arms around his waist and hugged him and he put his big strong arms around my shoulders and squeezed me tight. I felt so tiny and helpless in his arms and I definitely felt his already hard cock pressing against me. Feels like you glad to see me" I said and as we separated I pinched his cock thru his jeans. Damn things been hard all friggin day Rexy'.
"So when do we get champagne?" I laughed and Lawrence opened a bottle and filled our glasses, then handed me one. `What shall we toast to?' he said holding up his glass.
"Mmmm, lets see.I know.lets toast to me sucking that big hard meat of yours" "And filling you hot sweet ass with cum?" he added as we smiled at each other and clinked glasses. I took a sip but lover boy downed the entire glass in one big gulp. "Fuck baby!" I said then did the same with my glass causing a wide grin on his face. Lawrence poured us another and also handed me the gift and asked me to open it. I did and inside was a very expensive looking necklace. It was silver with a heart outlined with small diamonds and I loved it. "Oh Lawrence it's beautiful, put it on for me" I handed it to him and turned around, lifting up my hair so he could clasp it on the back of my neck. After he did he bent down and kissed my neck softly as he put both hands on my waist and ground his crotch into my ass. I felt a chill run down my spine and I wiggled my ass into him and pushed back.
As much as I wanted to prolong the evening and savor every minute, the alcohol kind of hit me or was it that I was so fucking excited, but I felt tinglely all over and light headed.
"Gawd Rexy I need to fuck you" I looked over my shoulder at him as he was dry humping my ass and smiled at him.
I let this go on for a few more seconds than I turned around to face him.
"Oh Rexy Ann, you are so beautiful" he said looking straight in my eyes.
Right there in the kitchen I reached for his belt buckle and undid it then the button on his jeans. With our eyes locked and a smile on both our faces I very slowly pulled down his zipper.
"Take your pants off"" I whispered in his ear. Lawrence shed his shoes and socks and removed his pants like they were on fire as I reached for my purse took out my lipstick and reapplied some more lipstick for him. "Damn your lips are so hot baby, suck me"
Lawrence leaned against the kitchen counter and I squatted in front of him on the tile floor and reached for his cock. I stroked it and it felt so warm and hard. I couldn't believe after fantasizing what it would be like I finally had a cock in my hand and inches from my lips. It was much bigger than my cock and it was beautiful to me. I admired my red fingernails wrapped around it, as I stroked it, I was in a trance.
"Suck me bitch" I heard him say but it sounded muffled and far away. "Suck me you fuckin little whore" he said and I moved my lips closer. First I licked then kissed the tip of this huge black cock in front of me, then I pointed it up and kissed the underside, starting at the tip and kissing my way slowly down to his balls.. His huge, heavy balls. Still holding his cock up I cupped his balls in my other hand. His balls were so big I could only fit one in the palm of my hand. I kissed it and licked it.
"That's it, baby. Suck my big black balls you cunt"
I licked and gently sucked his balls, alternating between them, covering them in with my red lipstick. I felt like I was dreaming this, it didn't feel like it was really happening to me.
My own cock was straining to get out so I reached in and pulled it out over the top of my panties.
"That's right baby, let's see that little clitty of yours" "Are you my little whore Rexy Ann?"
"Yes baby, I am your hot fucking little whore"
"Then suck my black dick whore"
I felt so submissive and helpless. I realized that I love a man in charge and I will do anything my man wants. I want only to please him..
I took his cock and slid my lips over it. Lawrence put both of his hands on the side of my head and fucked my mouth, each time deeper in my mouth. I felt it hit the back of my throat and I felt like I wanted to gag at first but I didn't. I opened my throat like I was swallowing and his cock slid down, each time choking me just a bit.
"You are such a cock whore baby" "Uhguhh" was all that came out with his cock down my throat.
Lawrence suddenly stopped fucking my mouth and pulled out his cock. "Get up baby, turn around. He pulled me up and bent me over the kitchen table and pulled down my panties.
"Wait a minute baby" I said, and I reached into my purse in front of me on the kitchen table and pulled out a small bottle of baby oil, and still bent over I handed it to him over my shoulder. He took it from me I pulled out my lipstick and as I was coating my lips I felt baby oil run down the crack of my ass, then I felt his hand sliding down my ass rubbing it in. I dropped the lipstick when I felt his finger first circle my ass pussy then effortlessly plunge in. I opened my sphincter for him and he begin finger fucked me.
"Like that whore?" "Mmmm, yes" "Like my finger in your ass baby" "Ooooh yesssssss" "Want my dick in there baby?" "Yessss"
I think he put in two or maybe three fingers in my ass and was fucking me faster now.
"Say it whore, tell me you want me to fuck you" "Fuck my hot little ass with your cock baby" "You want my black dick in your white whore ass baby?" "Yes, I want it" "Want what baby, say it" "I want your big black cock in my hot fucking whore ass baby. Fuck me!"
I was so far off in space by now; it was like I some strange erotic dream. It didn't seem real in some ways but very real in others..
Lawrence stopped fingering me then I felt more baby oil squirt down the crack of my ass. I arched my back and stretched my legs up to offer my ass to him. I felt the tip of his cock against my ass as his hands reached around and fondled my breasts. He was teasing me. His cock poking my opening but not penetrating me. I pushed back and I felt the head slip half way in then slip out.
"You want it whore?" "Yes baby" "I have some friends of mine I want you to fuck baby. Will you do that for me?" "Yes, baby, yes"
Lawrence slowly pushed his cock into me and I pushed back. It hurt just a little at first but it hurt in a good way. I opened my sphincter and his cock slid in deeper. I felt so full and so damn feminine and submissive. It wasn't like with a dildo at all, it was much, much, much better! Lawrence started slowly moving his cock almost out of my ass then slowly back it. It felt just a little deeper each time. I couldn't tell how far he was in me but it felt like he was buried deep in my ass. I reached around and felt his cock and to my surprise he was in me maybe 4" with at least another 4" to go.
"Oh baby your ass is so tight and hot" "Mmmm" "Like my dick in your ass, whore? "Mmmm" "I want my friend Jerome to fuck you baby? Mmmm" "And maybe Leon, and Oscar too baby?" "Yes baby, yes, I want all your friends to fuck me" "Gawd it feel so good baby" "Ohhhyesss" I said as we picked up the pace.
I lifted one leg up on the table and Lawrence grabbed my ankle with his hand. "Gawd you're so fuckin sexy" "I need more baby oil baby" and Lawrence emptied the bottle down my ass crack. "Yes, that's it, don't stop" "You're going to make me cum baby" "Yesssss, shoot your hot cum in my ass baby!"
Lawrence stiffened and I felt him push it in all the way deep in me and squirt then pull back and squirt, then again and again and then again. We were both breathing heavy and trying to catch our breath and didn't move. I felt his cock shrinking in my ass and pushed back into him and Lawrence pushed one more time then pulled back and his cock made a plop sound as it came out of me and I felt his cum dribble down my inner thigh. I turned around and with wobbly legs I put my arms around his neck and he put his around my waist and we kissed.
Lawrence noticed my clitty was hard and told me to make myself cum while he watched. I grabbed my cock and started stroking myself as he sat down in the kitchen chair and watched. "Cum for me baby" "Talk dirty to me baby, I am your slut whore, I wanna cum for you"
"Stroke that little white clitty for me. I want you to shoot your cum on my ball and lock it off, you whore" "Yes baby, spread your legs"
Lawrence leaned back in the kitchen chair and spread his legs for me. I lifted up the front of my mini skirt and pointed my clitty/cock toward his cock and balls, and Lawrence stroked my stockings as I feverously pumped my clitty.
"Cum on my big black balls and lick it off you fuckin whore"
That did it. I felt it start deep inside and I shot several spurts of cum all over Lawrence's crotch and didn't hesitate to drop to my knees and lick it up from his cock, balls and stomach.
After I finished I looked up at him and he smiled.
"That was fun" he said. "It sure was different too" I replied
Lawrence helped me up and I took a peek at myself in the hall mirror and was pleased that my make-up was mostly intact, except my lipstick, but I did look like I just got fucked by the entire Marine Corps.
Lawrence wanted to keep going but I was pretty wrecked so we sat on the couch for a while and talked and he left around 11:30. We had a nice little make out session at the door and agreed to hook up again soon. As he walked out the last thing I said was "Bring Jerome with you next time"..
I took off my high heels but crashed on the couch still dressed and slept all night. I woke up about 8 the next morning with a nasty hang over and my ass was a little tender but I my first thought was to hook up with someone else tonight!
To be continued...lots more to tell