Crossing Over to Cross DressingbySluttyValerie©
I had over time developed some kinky sexual tendencies, I was fascinated with lesbians and always wanted to get in a three way with two of them. I read stories about them and rented tapes and then DVDs. Lesbians, Lesbians, Lesbians....mmmmm I just could not get enough of them. Fantasy is one thing and reality is usually something opposite. My Lesbian quest still lingers and I realize it will not likely pan out.
For a long time I had and still do have the BDSM, dominant female sub male kink. That one was easier as there are professional providers that supply the fantasy. I explored that facet for a while and it was really fulfilling but expensive. I had a few regular providers. Those stories I guess will eventually be written, and there are some really good ones too. In a way my BDSM kink led me to write this.
Part of the lure of the female dominatrix was total submission. The thing that really boiled my blood was being feminized and then fucked with a strap on. When I occasionally got what I wanted, it was intense as hot as hell. The problem with this was that the Dommes that do it are really far and few in between. Going to a Domme and wearing some ratty female clothes that dozens of other perverts like me wore was not appealing. So I started acquiring my own wardrobe. It got pretty extensive, heels, wigs, sexy lingerie, skirts, dresses, and the whole package so to speak. After a while my blood was no longer boiling and I wound up moving and essentially leaving my known favorites. I discarded all my play things and refrained from the scene. It had gotten the point where I did meet nonprofessionals and had several group play events.
Looking for a place in a new city that you don't know is tough. I had a real estate woman help me find a waterfront condo, she was older by about ten years than me but still well put together and quite attractive. We eventually hooked up; I offered to take her out as thanks for her work after I moved in. We went to dinner and back to my place, she was divorced and tired of middle aged divorced guys trying to get at her honey pot. We started a torrid affair, I fucked her silly and she was appreciative as most of the guys she dated came once and were done, we fucked all afternoon and into the night, she lost her inhibitions and sucked my cock and swallowed my cum. She never had swallowed cum until we met, she always told me how good I tasted and that her husband's cum was disgusting and she spit it out on the rare occasion that she sucked his cock, usually once a year on his birthday because he begged her. She wasn't a complete prude by any means. As we went on, she opened up and started telling me about her sexual escapades. She told me of how she had a few lesbian affairs when she was married, try as I did, I could not get her to bring another woman into the picture.
She was about 5'8" and 125lbs and sandy blond shoulder length hair, nice 38Ds with big brown areola and big eraser nipples, I loved sucking on them and she loved having them sucked. Her stories continued when we were in bed she would tell me about the time her husband was drunk and essentially raped her. To get back at him, she got a strap on and got him drunk and fucked his mouth and ass with the strap on. I told her that it was the hottest story I had ever heard and over time told her I wanted her to do that to me. She also told me about a lawyer she dated, when he had a big case in court she told me that he would dress in women's lingerie under his suit and tie. Again I told her how hot that story made me, she figured it out as I had a hard on that she sucked until I came in her mouth.
She started playing porn on her TV in the bedroom when we were fucking. She said that she bought dildos and they sent tapes in the pack, probably a lie but I said OK. She wound up showing me a collection of porn that you would not believe. The more I got to know her the kinkier things got.
Circling back to one of the things I told her about the strap on and wearing lingerie, we were between fucking and sucking and lying on the bed watching porn and she got up and put on a different video. This one had she-males fucking guys. My cock jumped and started to grow, she said "I thought you might like this" and started sucking my cock, she slid up and down my shaft and took periodic breaks to talk dirty to me. Telling me she wanted to see me take a shemale cock in my mouth and then watch as I got fucked in the ass like a bitch. This dirty talk was sending me into a different realm of hard on and it kept up, she sucked me, then stopped and talked dirty, she flipped around and sat her soft pussy on my mouth and we settled into a burning hot 69. I ate her pussy like I never had before. She was hornier then I had ever experienced. She bucked down on my face and grinded her pussy lips up and down my face. She came up for air and stopped sucking my cock and just rode my face while she screamed how she was going to dress me up in her clothes and fuck me with her strap on like a bitch.
She flooded and actually squirted pussy juice all over my face, I actually swallowed a few mouthfuls of her hot sweet sticky nectar and I was still covered with cum. She fell between my legs and sucked me off, I blew a load like I had never done before, I was in her complete control and that was strange as I had pretty much dominated her and fucked her silly at my whim until that day. Oh my god! This is true and not wishful thinking.
The next time we met we went to a sex shop and bought dildos, butt plugs and a strap on. I paid for the items, of course there was a woman at the cashier and Jane went out of her way to tell the girl that she was going to use all of it on me after she dressed me in her clothes. Which is exactly what she did, hot as hell. I basically did what she wanted and never said no. She went into her closet and picked out a few things and told me to put them on, black stockings, black panties and bra. No shoes as her feet were smaller than mine. I said to her "what no skirt or blouse?" She laughed and came out of the closet with a skirt and blouse and had me put them on too. The sex toys were totally hot and she kept telling me how she was going to go back to the store and get the female cashier and bring her back to show her how I looked all dressed up.
Eventually, she wound up moving halfway across the country and we lost touch. My attempts to find a replacement never materialized.
Some time elapsed after she left and I continued my kink by myself, watching porn and searching for a replacement.
I had two back to back business trips scheduled and I was packing for a long trip and had a big bag that would need to be checked. Then I had a bright idea, I could drive my car to the second city of the trip that was only about two hours from home, I could fly out of that city to the first meeting in Las Vegas, then fly back have my second meeting and then drive home. Then I would not have to pack one bag for the whole trip. I took the stuff out of the big bag and packed two smaller ones, leaving one in the car for the second part of the trip. No checked bag, no problem!
I get to Vegas and I have about 2 hours to my first meeting, yes Vegas, business, no fun. It's hot as hell in Vegas as expected, so by the time I get to the room I am soaked in sweat. I grab a shower and come out open my bag and realize I left all the under wear in the other bag in the car. I run down to the Lobby of the MGM where I am staying and none of the shops in the mall have underwear, unbelievable! I also have no socks as well. I run out side and look around and see no prospects, unbelievably, a souvenir stand for some unknown reason has a bag of socks for sale. Sock problem solved! Now it is time to decide whether I go with no briefs or press on. So I get in my rental and set the GPS to a shopping center that will have what I need.
Well the story doesn't get any easier, the traffic is horrendous and the 5 miles to the store becomes a bridge too far. I am about to turn around a go back and see a drug store. I pull in and hope for the best. I go up and down the aisles no luck. The last aisle down the far end has packs of underwear, but they are women's panties! So I am staring at the display and decide what the hell, but what size to pick and what type? There is a four pack of panties that are not too skimpy, but definitely feminine. I need four and decide to take medium as I am fairly slim, large might be too big and small, well you know, it's like Goldilocks.
I get back to the room and I am soaked in sweat again so I take another shower. Now I have 4 panties, white, tan, black and pink. I figure to wear the black on the plane as they look the most like men's. I put on the tan and immediately feel the silky smooth feel to them, hard on ensues and I get dressed and go to meeting semi hard. I cannot stop thinking about the panties the whole time I am wearing them.
The second night there I go out with friend and we meet a few ladies and we are making headway with them. Mine is a cute brunette there to gamble and party. My friend is very smooth and a ladies man all the way, he always winds up with chicks. He paves the way for me and later I am on the elevator up to my room with the brunette. Oh yeah, now I just happen to have the pink panties on, what in God's name am I going to do? She has already rubbed my crotch and said how much she loves oral sex especially 69. I told her that was my favorite too, which is true.
I only turn on one light and we make our way to the minibar and pop the small bottle of wine. What the hell I think to myself, I am never going to see her again. So we start making out on the bed and we strip down, she sees the pink panties and asks me if I always wear women's undies? I just said "sometimes" She says "standup" I stand up and she motions her hand in a circle and I spin around. She says "Damn, you look cute as hell in those, I'm jealous."
We fucked and sucked like nobody's business, she wanted to see me again the next night so I said OK, she asked me what I would be wearing and I told her I would surprise he, then I said "let's trade." I kept her much smaller panties that were dark pink mesh with little bows and she took my light pinks silkies. I said, "Now you know what I will be wearing."
The next morning I put on her panties and of course, got stiff. The whole day I kept getting hard, the mesh of these panties was a different feeling than the silky one I had on. I went back to my room at lunch and lay on the bed and jerked off, careful not to get any cum on her panties as I figured she'd want them back later.
I met her at a bar and we had a few drinks and then went to dinner. On the way back she wanted to stop at a strip joint and check out the place, her friends said they would not go to a place like that so she wanted me to take her. Of course I was game, Gina got into it after a few more expensive drinks. She was slipping bills into garter belts and thongs like she had been doing it for years. She whispered to one of the dancers who eventually came over to us and did the customary chatting before they hit you up to spend more money. This one was a knock out (like all of them) a tall blond with big tits and nipples. She came over and sat on my lap and started grinding her crotch on mine. I got hard and she was intent on making me cum in my pants. I could not resist and went with it. After last night and the load at lunch, I knew I would not have too big a load. She was flopping her tits in my face and grinding hard on my crotch when I came. She bit my ear in a playful way and said "I hope you clean her pink panties before you give then back to her."
I almost came again.
Back to my room for round two which is now hotter than last night. She has my silks on and I have her mesh panties on. She kept telling me how she never would have thought that she would get turned on by a guy in panties and that all her guys from now on would wear them. I wound up convincing her that I should keep hers and she could keep mine. I promised her I would wear them on the plane back east, which I did. I went to the bathroom a few times on the plane to check them out.
So that is how I was reintroduced to wearing panties and eventually wearing more and more women's things. I thought I would throw each pair away as I wore them on the trip but I wound up taking them back with me. I wore them on most business trips and started buying more and more, panties, bras, pantyhose and stockings. I would wear them while I was traveling on business. I had a storage unit for company goods; I kept my "things" there in a suitcase. Eventually I acquired breast forms, wigs and an assortment of sexy heels as well. I can virtually pass and recently went out in public.
The story progresses.....stay tuned....this is all 100% true.