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Full Version: She turned me out, my first time out in public as a woman
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I have always been a closet crossdresser ever since the early days of puberty when my hormones started running wild. I had this uncontrollable urge to become a woman, I so envied ladies having the opportunity to wear all the sexy lingerie, bra’s panties, stockings etc. but ultimate favorite I think had to be girdles. Not so fashionable these days but back when I first stepped over the line and tried on my first bra (my mother’s) girdles were in fashion at least in the days of her generation. She had a collection of full longline bras, bullet bra open bottom girdles panty girdles with garters you name it I was in crossdressing heaven. On the days when I was left alone because my mother was a working woman back when it was unheard of, as soon as she left and most likely wasn’t even off the block and I was changing into a bra and girdle. I had this obsession that bras and panties had to match of course because all the models in the catalogs did. My obsession carries through even to this day. As I am composing this story wearing matching bra and panties.


Well as I grew older, I knew my compulsion would not be accepted by anyone especially my family and friends, this was before the internet was even an idea in some brainiac’s head, those in the lifestyle today don’t have any idea what a blessing the net is for us. I moved out on my own in my early twenties and enjoyed my crossdressing in the privacy of my own place but always alone. I was very weary around girlfriends because I just had a sense about me after getting to know them as to whether or not my secrete would be safe and acceptable. Until one day strictly by change I met this girl named Kelly, the details of how we met are not important to my story but what happened with her is. We hit it off as sex partners and she became a non stop booty call which was fine for me, I did like her a lot but wasn’t quite ready to commit. Well one day after a good knock down drag out fuck session, she asked me to grab her bra that landed on the corner of the couch and toss it too her, I picked it up and was fooling around holding the cups of the bra to my chest and was rubbing my tits, She giggled and laughed an whistled oh my don’t we look sexy. I laughed and said you know it baby I could rock this no problem. She laughed and sad oh really Mr. She said well let’s see about that and she walked across the room and told me to put my arms through the straps, which I did she then told me to turn around and she hooked the clasps of the bra and said now let’s see how you look. As she led me to the full length mirror in the bathroom. We stood in front of the mirror with her naked behind me with her arms around me fondling my bra covered tits. It was an underwire with cups made of a shear fabric. I could clearly make out my areola and nipples. She started rubbing my ass and told me I looked hot, would you fuck me while wearing that please as she reached around to grab my growing cock as I was excited to be in the company of a female while wearing a bra. We went out to the living room and she grabbed her panties off the floor and said here put these on. My God they matched she was my kind of gal. We fucked and sucked for a while and I thoroughly enjoyed it as did she. She said to me come on we were supposed to be getting something to eat when you put on my bra. I said no I picked it up you put it on me. We got changed and ready to go grab a quick bite, but before we left, she grabbed a fabric measuring tape from one of the kitchen draws and told me to put my arms up. She measured me around the chest right at the nipples I knew exactly what she was doing but didn’t let on.

We went downtown to a little favorite Chinese place and grabbed dinner on or walk back we stopped into the sex shop where we had been to many times before looking at all the toys but didn’t buy any. We got back to her place fucked a bunch more times and then I had to say goodnight. She asked if I planned on coming down the following night for our usual fuck and food session, I told her I wouldn’t miss it. The next night I arrived after stopping home to shower and change, when I got to her place, she had a big smile on her face and said I got you a present, oh really do you now, what is it let me see. She handed me a bag from a local lingerie store that I knew because I passed it every night on my way to her house. I reached in and removed two bra and panty sets, one black and one turquoise, I gave her a big long kiss and thanked her. I said oh my, aren’t you the kinky little devil, she giggled her signature giggle and said well you looked like you were really into it so I figured you’d like your own, you can wear mine anytime you want though if you like. I smiled and said thank you I might take you up on that offer. She was especially excited as they both matched sets that she had, she pointed out that these had molded foam cups to give you bigger boobies and we can even fill them with something if you like. She confessed to me that she had a fantasy or possibly as much of a fetish for the longest time about wanting to have sex with a man dressed in her underwear. So, who was I to not allow the lady to have her fantasy, all the time I never disclosed to her that I was a crossdresser? We continued having our fuck and food sessions for months that grew into years we even still had great sex after we had both met our respective significant others mainly to satisfy our kinky side.

I mentioned that I met someone else while I was fucking Kelly, we talked on the phone at work daily and she had the sexiest voice and had to meet her I didn’t care what she looked like but of the opportunity arose I was going to stick my cock in her. Kelly being my friend as well as kinky lover said hey go for it let me know all the details, maybe I can even meet her some day and we can have a threesome. This totally shocked me as Kelly never mentioned anything of the kind before then she grinned and laughed saying gotcha! But hey you never know right.
When I spoke privately while at home with this new person of interest, she was a completely different person, she was a lot funnier and had a dirty mind and loved telling me dirty jokes. We spoke freely about sex and different things we liked but my secrete was still just that only shared with Kelly my fuck buddy, which btw wearing bras and panties were now a prerequisite to have sex, a few times she dared me to wear them under my clothes when we went out I am never one to back down from any dare.

Well this new girl Deedee was downright raunchy at times which was titillating to say the least. She told me she had friends who were transgender, gay, lesbian and straight. She said in the movie business you meet all types; I was impressed to say the least and asked about the movie things. She was a professional cosmetologist and wardrobe specialist. She had a laundry list of music video, movies, TV shows etc. in her resume. I asked her if she ever did any porn she laughed and said had several parts in some lesbian porno’s I said REALLY! She laughed and said fuck no I just said it to get a rise out of you… laughing. I said you win you got me, she said yeah, I bet something is rising right about now! I said ah hum you’ll have to come see for yourself, she quickly replied what’s your address I’ll be right there. Thinking I’d call her bluff as soon as I gave it to her she would back off, but she simply said let me throw some stuff in a bag and I’ll be on my way if I get lost, I’ll call you. I was like holy crap this broad just called my bluff. Well about a half hour went by and I heard a car pull in my driveway and there was a knock at the door. When I opened it there stood this 5’8” brunette with long legs that went from her feet all the way up to her nice firm looking round ass and sporting a nice big pair of tits that were busting out of her blouse intentionally unbuttoned just enough to show me she was wearing a black bra. She looked down at them and said that’s why they call me DD She was a ten plus that is except for her face, she wasn’t ugly by no means but plain is how I would describe her. I invited her in, and she no sooner stepped inside when she planted a nice long kiss on my lips with a slight bit of tongue. She said well after talking to you on the phone for year and even more so our more private conversations I feel like I’ve known you a long time. We went into the living room where I had a fire going in the fireplace and only had one light on next to the chair, I was sitting in watching the tube. She smiled and said very nice this looks like a great place to fuck with that fire all you need is a bear skin rug. I almost spit my beer through my nose. She laughed hysterically and said I warned you I have no filter when I am not at work. We sat next to each other on the couch talking and my attention kept going back to her nice looking rack. She laughed I said nice bra and smiled and said thanks figuring I’d one up her I asked so matching panties? She said no I never wear panties only when I have too, I hate the restriction. My attention now went to her stocking long covered legs, she quickly said I wear thigh highs sometimes but normally I wear garter belts. My cock started to go into launch mode. She pulled her skirt up and said see, pulling it up enough that I could see that she was telling the truth, I said nice view so far, she said nice? How’s the view now as she hiked her skirt all the way up exposing her pantiles pussy. My jaw must have hit the floor. She laughed and said what you’ve never seen a pussy before. I was not speechless but fumbling for words. I told you I like to shock people. I said I guess you do.

I placed my hand on her knee hoping to work my way up to that nicely trimmed pussy, but she placed her hand on mine and said woe slow down there big boy all in due time. She said wait I have to show you something as she took a healthy swig from her long neck beer and reached for the big bag, she had brought with her. She pulled out a photo album and sat closer to me as she thumbed through the pages. Here were the pictures to back up everything she told me about her movie/video career hell she even won all kinds of accolades for her work. She got to one set of pictures where she transformed this guy into a woman. I was drawn to it like a month to a flame. I said that’s amazing I’d swear that was a chick I’d hit on her if I had half the chance, she laughed and said yeah, you’d probably wouldn’t know what to do when you reached up there and found a cock. We both laughed I lifted her skirt and said just checking. No cock up here honey well not yet anyway she smiled. We sat there drinking and chatting thoroughly enjoying each other’s company. We necked a little and I was fondling her tits gently squeezing and playing with her nipples through the material, when she stopped Frenching kissing me and said hey, I have a cool trick to show you, I said go for it.
She removed her one hand from my neck and sat back and spread her legs and took her longneck and slowly inserted the opening into her pussy that was by now soaking went. She fucked her pussy a few times and then removed the bottle and placed it to my lips and tilted it back and said here you look like you need a drink. That was the best beer I had ever tasted. She stood up and took my hand and said ok enough teasing lets fuck. I said it would be my pleasure. We got to the bedroom where we took off our clothes, I admired her beautiful body in the sexy black bra and garter belt and stockings. She put her hands behind her back to unclasp the bra and I said no leave it on please. She smiled and said sure but let me adjust it first. She flipped down a panel on the top of each cup exposing her nipples. I smiled and went in and pinched and sucked her nipples. She took my hand and was leading me to the bed when I said wait. She had this what the fuck look, on her face, I stripped the heaving comforter and blanket off my waterbed and reached into the wicker basket at the foot of the bed and pulled out another heavy blanket and handed it to her and lead her back down the hall he pumps clicking on the hardwood floor. I said your right this is a great place to fuck. I spread everything out grabbed the couch cushions and we both lay in front of the fire and proceeded to fuck our brains out. After our second time she said she’s like to go on a cruise on your waterbed. I smiled and said you got it. We picked up everything and back to the bedroom we went for a sex cruise on my waterbed. That lasted until the next morning.

It was one night a few months into the relationship I just arrived at her house I just got there when she was getting home from work we went inside and she kicked off her shoes put her feet up on the ottoman and asked if I would rub her feet, something I am really great at according to every women I’ve been with. So, I’m there rubbing her feet and she undoes the belt of her dress, and opens it giving me full view of her uncovered pussy and her matching of course bright red bra and garter belt. She said help me off with this thing will you please. So, she sits up and I place my arms around her back and unhooked her bra as she kissed me. She let out a sigh of relief. She said I hate wearing these dam things sometimes they can be so uncomfortable, I laughed and said quit your bitchin how bad can it be to look that damned sexy. She laughed and said ok, so you think it’s easy huh. I laughed yup. She got up from the chair and sauntered off to the bedroom her open dress flowing and her untethered tits bouncing, she returned with a purple padded bra and said here you go smart ass, put it on. I looked at her and she said you heard me put it on now! I said ok no problem. I peeled off my shirt and threw it on the chair. She said ok now put it on, I didn’t do the reverse trick and then slip your arms in as I do at home. She steps behind me and hooks the bra closed putting a finger in between the strap and my back giving it a little tug. She turned me around and said ok now do the runway walk for me and show me how sexy you look. I did as she asked and she kissed me and said you look hot and throws me my shirt, put it on your taking me to dinner and you’re wearing that, so we’ll see how comfortable it is. Jokingly I said what no panties. She said ok smart ass take your pants off and back to the bedroom she goes returning now with a purple satin garter belt that matched the bra and a pair of black stockings. She threw me the garter belt and said you know how to take it off I’m sure you can figure out how to put it on, which I did with ease. She pointed at the ottoman and said sit! I did as commanded and she put on one stocking at a time rolling it up my leg until it was just high enough on my upper thigh and affixed them to the garters and snapped the clasp closed. She pointed, saying walk and I did as she ordered. She told me to do a turnaround as she picked up her bra and put it back on.

She said you look sexy as hell now put your pants on and take me to dinner you slut. We went out and I was completely at ease with it and comfort wasn’t an issue it was really good/expensive bra so it aided greatly to the comfort level and the nylon stockings felt fantastic and the spirit of us matching outfits I wasn’t wearing any panties which I would have naturally done at home. She told me she was thoroughly impressed we enjoyed more than a few cocktails with dinner seeing how it was a Friday night and we didn’t have to work the next day. When we got back to her place the first thing, she did was undress and while standing there completely naked she looked at me and said are you going to, stopped and said no keep them on I kind of like it, it will be like fucking a shemale. Told you she was raunchy at times. We fucked and sucked, and I was clearly the sub. She got into it right away calling me her bitch telling me to eat her pussy clean of cum whenever I dumped a load into her. Sucking on my bra covered tits and pinching my nipples.



Afterwards we lay there, and she asked how’d I like being her bitch, I told her it was fun and that I really liked it a lot. I asked her would she mind if we do it again, she raised up supporting herself with one arm looking down at me, asking wearing this or something like it? I said yes It felt very erotic. She laughed and said you like to dress in women’s undies don’t you. I laughed and said ok you outed me I’m a crossdresser but jokingly. Now Deedee was wild and uninhibited, but I still tread lightly with my fetish well I was soon to find out that was completely unnecessary. She looked at my face intently and said you have nice cheekbones nose shape is good, you’re not too muscular, an athletic look would work. I had a puzzled look on my face, when she told me just leave everything up to me babydoll, lets fuck some more before bed we have a busy day tomorrow. I had no clue as to what was instore for me, but it had my cock twitching that was for sure. The morning we woke up with a morning blowjob with her spitting my load in my mouth and French kissing me, she sucked and play with my cock getting me hard enough to fuck which I willingly did filling her pussy full of cum, she commanded me to lick her pussy clean. As I did, she started talking to me. Lap up that cum you whore bitch, swallow every ounce of cum you little slut. I had no issue with ever cleaning a pussy of my own cum, but this was more exciting with the way she was talking to me. She sat up in bed and said I have a proposal for you, I said I’m listening, you seemed like you were thoroughly enjoying yourself last night wearing my bra and dressed like a slut I nodded yes it was wild I did enjoy it, she smiled and said good how would you like to take it all the way she asked, the full experience I’d like to transform you into a woman if you’d allow me the pleasure. I looked at her and she said well what do you think? I looked back at her and said why not. I have a confession to make, she asked what is it. I hesitated a little and then just let it fly I’ve been a closet crossdresser for years. She smiled and said really do tell, I think it’s very cool I really do I’ve never had a CD boyfriend this is going to be so much fun with you’ll see, it will be nothing like anything you’ve experienced before.

When we were all finished, we showered got dressed and headed out for the day. After breakfast we hit the mall and several small shops she frequented. We went to Victoria’s Secret, Fredericks and some trendy store where she shopped. She picked out bras and matching panty sets stockings lingerie, nighties etc. and two boxes containing shoes. She smiled and said nothing but the best for my bitch. I was like ok this is going to be fun. She made two more stops both of which I had to wait in the car. When we got home, she ordered me to the bathroom and said draw yourself a bath which I did she assisted me in washing everywhere and said ok now let’s see one of those legs. She sat on the edge of the tub and lathered my leg up with shaving cream
And proceeded to shave my legs, she said in the future you’ll do this yourself and explained exactly how to do it with the least chance of nicking yourself. She then had me raise my arm and she trimmed the hairs with a small scissors and then shaved me clean. She commented this too is something you’ll need to do you’re not from France meaning how many French women did not shave their armpits something we take for granted but when you see it that’s disgusting if you ask me. She then saved my face closer than I had ever done in my life, she gently guided the razor across my face alternating direction she explained this was to eliminate razor stubble and leave my face baby soft n smooth. She said ok last step and she lathered my chest with shaving cream and drew the razor across my chest within a few minutes she had voided me of my body hair except she smiled and said yes down there too. She had me lay flat on my back on a bath towel on the bed. She methodically trimmed my pubic hair until I was ready to be shaved. She lathered me up and proceeded to shave me clean she even held my cock up so she could shave underneath it and my balls as well. She was very gentle and careful not to nick me at all before I knew it, I was completely bald, with the exception of overall size my body resembled that of a prepubescent young boy with a really large cock. She moved it up and down and said we’ll have to do something with this, but I have just the trick. She reached into a draw in her dresser and pulled out what appeared to be a thong, but it wasn’t the look on my face must have said what it that. She said this is a gaff, I asked a what? It’s called a gaff it's designed to hide your penis and it will help prevent you from getting an erection. I said but I like getting erections and she said so do I but not when your dressed as a woman, a woman with a dick is a shemale, we’ll let you be a shemale later.

I stood up and she had me step into it and slipped it up my waist and told me shove your cock in here pointing to the tube looking part of the device, When I did she reached between my lags and tugged it pulling my cock between my legs and she affixed it to the back of the waist portion of this gizmo. When I stood in front of the mirror my cock was gone all I could make out was a fleshy bulge. She said this way your crotch will have a feminine look, she then said ok bra and thigh high stockings for this afternoon I have a different outfit in mind for tonight. I sat down in the large wingback chair in her bedroom and proceeded to roll my stocking on over my foot first then rolling it carefully as I pulled them up into position I ran my hand palm down the entire length of my leg smoothing it out I then did the same with my other leg, the feeling was so much more incredible with my freshly shaven legs. On the back of the chair was a black satin bra with red lace trim, I put both my arms through and turned around so she could hook me up. She smiled and said I bet you’ve taken hundreds of these off without a problem but putting them on is a completely different story isn’t it. I nodded yes, it is, and I don’t know about hundred she laughed and said oh no not you. She stood facing me and smooth the cups of the bra out with the palms of her hand, she looked and said hmm I think we’ll need to get you some with molded cups but for now these will do. How does it feel I answered honestly a bit tight, she said you’ll see why in a minute, she walked over to her dressing table and reached into one of the draws and came out with two pads she pulled each cup and slipped this pad under my man boob forcing it upward, she then did the same with the other one she pushed up the bottoms of the cups and smiled and stepped aside giving me full access to the full length mirror and my God I had cleavage, not a lot mind you but some cleavage nonetheless. She said well you’re a natural B cup, but a C would suit you much better. I smiled and said how about a D or a Double D. She said my now aren’t you the big slut. I said well if I am going to be your slut I might as well try my best. She laughed and said we’ll get you some larger bras and work on that, I think you could pull off a D cup or DD as we are exactly the same height and I think mine look pretty damn good. She then handed me a black underbust corset which I stepped into and she assisted me in pulling it up to the band of my bra and proceeded to zip it up from the back this was to give me more of an hourglass feminine figure. It was tight but held everything in its place. She asked if I was ok and was it too tight and did, I have problem breathing? I said no it’s a bit snug but I’m ok. She laughed and said I’ve worn that on many occasions. I looked and said really why, she said sometimes a girl just has to accentuate her curves to overpower the male species, especially when I am at work and I want what I want I use my body as a weapon when I have to. Impressive I thought to myself


Ok next your makeup and she patted the bench in front of her dressing table, she then went to work foundation, lip gloss, she used a pencil and some brush to highlight my cheekbones, eye liner and eye shadow. She took some coverup and tabbed it on her finger and she ran it over my upper lip hiding any hint of a shadow where a mustache was supposed to be. She was talking to me the entire time directing me what to do with my lips etc. she said I don’t want to make you look too whorish right now we’ll save that for later. Now I normally would let you take a peak, but I want to wait, she then brushed my hair back and said when it gets longer, we’ll style it but for now we must hide it. she took the cap that looked like a nylon stocking and slipped it on the top of my head pulling it down and smooth it out. She then reached for one of the wigs a shoulder length auburn/red with a light curl. She applied some sort of adhesive to the underside of it and firmly laced it on my head saying that so I don’t rip it off when I grab you by the hair when I fuck you She ran her fingers through it and then worked her magic with the brush and flipped it with a comb. She smiled and said you look great one of my better jobs if I do say so myself. She stepped away from in front of the mirror and said well what do you think? I could not believe my eyes a beautiful woman was looking back at me. I was speechless. Trying to find the right words or any words at all I said oh my god your amazing I actually do look good. She said good enough to eat, I smiled and said hmm. She took my hands and did my nails and we chit chatted like girls do in the salon, she said fun isn’t it, I said yes it really is. She painted my nails with a nice shade of red commenting this is one of my favorite colors, she put cotton balls between my toes while the nail polish dried. She told me normally I would put your wig on after the dress, but I just had to see your face. I’m glad she did as look at me half done wouldn’t have been as effective. She said you’re ready to get dressed as long as you're careful with your feet and don’t mess up my work. I told her I’d try my best, ok she said and pointed to the dressing rack over in the corner of the room.

There draped over a chair was a black leather skirt and hanging on a hangar was a deep red satin blouse and a waist length leather jacket. I walked over carefully not to mess up her polish job and reached for the skirt first. She said no you’re not a guy anymore stuffing his shirt in his trousers you’re a lady, blouse first. I did as she suggested putting the blouse on and buttoning it up. I then reached for the skirt and she told me to step into it with the zipper in the back, I did and wiggled my ass as I pulled it up over my hips I took my hand and tucked the blouse into the waistband of the skirt and like she had smooth everything out so there were no wrinkles. She told me the jacket could wait until we were ready to go. I was thinking to myself go I’m going out dressed like this surely as soon as someone looks at me, they will know I’m a guy. She then handed me the short boots she picked out for me unknowingly with my credit card. She must have sensed my fears and said relax babe kissing me on the lips you look better as a woman than you do as a man no offense. She said let me get ready and we’ll go out.

She quickly got out of her cloths and stripped naked in a flash she put on a fresh bra and slipped on a pair of black stretch riding pants with no panties and her cameltoe was clearly visible she then slipped on her up to knee black pirate boots and a black satin blouse, finished off with her leather duster. She handed me a purse and said remember how I taught you to hold and carry it, I nodded ok and she said one last finishing touch, she stood in front of me and tied a black satin neck scarf and adjusted it so the ends were to one side this would cover my Adams apple the one true telltale sign that you are not who you want people to believe you are. She took my hand and squeezed it asking are you ready, don’t be afraid to say no I’ll understand. I mustered up the courage and said no I’m good let's go girlfriend. Truth be told I was scared shitless, but most of all I didn’t want to disappoint DD she had worked so hard and trained me for so long, not going out in public would be like not showing up for your college graduation.

We got into her car as two girls going out for the afternoon in a lifted pickup truck wouldn’t be very convincing. We headed off and she drove us to a spot she knew a few towns over just in case, but I didn’t know a soul in that part of the state other than her. She picked our destination purposefully a small town on the border that was frequented by members of the gay community so as to give me reassurance that we would be amongst a nonjudgmental crowd. We had a fantastic time we shopped and had lunch and drinks like girlfriends do it was a glorious day. While in one of the trendy boutiques there was a gay male couple shopping and one of them stopped dead in his tracks and said oh my God! I love your outfit you look fantastic and without giving it a second thought I thanked him for the compliment instead of saying nothing or a smile my voice clearly gave me away. He smiled and said I love your shoes too sweetie, you two ladies enjoy the rest of your day, we both said you too. DD smiled and said see its fine your perfectly fine here your amongst friends, I just said I guess so, she reassured me by squeezing my hand and told me to relax. We continued on enjoying our day and hit a few more trendy shops and picked up some nice lingerie.

When we exited the shop there were our two new friends and the chatty one said oh my, did you find something nice here, I hope. DD opened the shopping bag to reveal a sexy white satin camisole, he was very polite and asked if we minded and DD smiled and said no not at all as he reached in the bag and held it up and said Oh my God this is exquisite you are going to look so good in this I can’t stand it. I just smiled DD replied he I mean she is a little shy this is our first day out. He smiled and introduced himself I’m Kevin and this is Bill he returned the cami to the bag and held my hand and said good for you both sexy and classy DD said he I mean she doesn’t think she’s convincing. The both of them said oh no, are you kidding you’re a ten plus sweetie absolutely perfect hell almost enough to make me go straight oh wait you’re a oh never mind we all laughed.

That was a tremendous confidence booster to say the least DD said well we have to get going but we come here often so maybe next week we can have a few drinks or lunch. They both loved the idea and said it’s a date, we gave our goodbye hugs and kisses and Kevin kissed me on the cheek and said I’d love to kiss you on the lips but don’t want to mess up your lipstick we all laughed and parted ways.
Mercy me!!! After reading that, I need a cigarette, and I don't even smoke.
Thank you, I plan on posting the rest of the story today