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A tribute to JoyI had always loved women’s clothing. Well truth be told, I had always wanted to wear women’s clothing. I envied women’s ability to change their look with just a little effort, a tight skirt; that was so sexy in one way to a pair of jeans that was sexy in an entirely different way. Then there was the hair thing. I thought that it was so cool the way that women could change their entire look, even their personality by just wearing their hair differently. I really like women. If it wasn’t for that monthly thing I would want to be a woman. I would be a lesbian if I had my final sexual preference. So one day when I was travelling on business I decided I would try on some women’s clothes just to see how I would like wearing them. I didn’t want to go to a major department store, the embarrassment factor I guess. I didn’t know what sizes I wore so I knew I needed some help. I worked up my nerve and decided to go to a sex shop. I thought that since I was going to try cross dressing, a store that specialized in selling g things for sexual pleasure was the best place for me to get started. I had never been in a sex shop before. I found the address, worked up my nerve and turned into the parking lot. I looked around to make sure I didn’t see anyone I knew. In my mind I played the conversation over and over, “Hey what are you doing here?”“Oh uh, I thought I had a flat tire and I pulled into the parking to check on it” Finally I thought, “What the fuck are you thinking? You are two thousand miles from home and you only know three people in a city with a population of nearly three million.”I got out of the car and hurried to the door I noted the sign on the door they would be closing in twenty minutes. I pulled it open and stepped into the store. I knew what I wanted but I didn’t know if I would be able to work up the nerve to ask for it. I kept looking over my shoulder as I browsed the merchandise displayed. ”What the hell would someone use THAT for? Hmmm now that looks interesting.” Some of the stuff looked cheap and ridiculous. “Who the fuck are you to pass judgment? You’re the one who is actually in a sex shop to buy women’s clothing.”“Hi, may I help you find something?” I nearly jumped when the young woman approached me from behind. I knew I was turning a deep shade of red. She seemed to be enjoying it. I gave her quick appraisal. I thought she was pretty in a way, kind of plain looking but certainly buffed out. Her glasses set her face off. I admire women who do the most with what Mother Nature gave them and she was a perfect example of someone making the most of what she had. She was wearing a very short black skirt, a gray top that was off the shoulders, a red bra whose straps showed over her exposed shoulders, black thigh high stockings and high heeled platform shoes. There was something about her; something couldn’t quite put my finger on.“Uh, well I was just kind of looking. I’ve never been in a place like this before.”“I see, well are you looking for something for yourself, your partner, or both?” She hit me with a smile that seemed to indicate she was reading my mind. “Uh, well I really don’t know.”She gave me a throaty laugh. I thought, “Talk about a whiskey tenor.” “Look you don’t have to be shy with me, I’ve heard it all and seen most of it. You should think of me like you would your doctor. You wouldn’t go to the doctor for head cold and not tell him about your broken arm would you? I can’t help you unless you tell me what you want. Believe me when you leave here you will be much happier if you allow me to do what I do best. Now tell me, what do you like?” I was still blushing like a school girl. “Well, I’ve always liked women’s undergarments.”“So would you want to wear the underwear or would they be for your partner?”I gave a deep sigh. “I don’t have a partner right now.”“Okay gotcha. Let’s step over here. I think I have some things you will like.”I followed her around some racks of various clothing items. My eyes kept being drawn to her ass and the way her skirt swung and swayed as she walked. Cute butt, I thought and nice legs too. I was getting turned on by her, was it because we were alone in a sex shop? No I’d hit on her anywhere. Then we were in front of a rack and shelves with some large sized bras, girdles, and garter belts, there were even high heeled shoes. When she stopped and turned around I stopped admiring her posterior and my eyes fixated on her small but well-proportioned breasts. She caught me.“Oh, sorry, I didn’t mean to stare. I was just looking at your name tag. Joy, that’s a great name.”It’s okay; this is a sex shop you know. I understand better than anyone that men like to look. I’m flattered that you seem to like what you see. Now is this what you have in mind?” She said as she picked up a black bra and pantie set. “Uh, yeah I guess so.””Silly man, you do you want to cross dress or not?” Again the smile, as she cocked her head slightly to the right flirtatiously.She really was cute. “Well, yeah I guess so.””You really are shy aren’t you? Is this your first time?” she paused waiting for my answer. “Yes. I guess so.”“It’s okay; I’ll help you, remember I’m your doctor. I think these would fit you nicely” She held up a black bra and matching lace panties. “Would you like stockings or pantyhose to go with these?”“Both I guess.” I was starting to feel more relaxed with her she had a way of making me feel at ease. She was like a doctor. I wondered if she gave physicals. “How far do you want to take this? Do you want breast prosthesis to fill out your bra? If you don’t want implants or hormone therapy it’s your best option. Unless you want to stuff the cups with something else or I could fit you with an A-cup.”“I think I would like the prosthesis.”She seemed to be warming to her task, satisfied that she had put me at ease. “Good choice. You have a nice slender body; I think you would look good in this.” She said as she removed a black pencil skirt from the rack. “How much do you think you’d like to spend?”What I was beginning to think about was spending the night with her. I did a quick reality check.“Really, she’s cute and works in a sex shop canlı bahis and you are seriously thinking about hitting on her? She gets so many offers she probably hates men who hit on her. Plus, she already knows you’re a cross dressing pervert. Why don’t you just go back to the hotel and send Scarlett Johansson an e-mail inviting her over, you’d probably stand a better chance.” So instead I said, “No real budget, I like your suggestions so far.”“Okay, these are C-cup prosthesis and will match your bra. They are the best, high quality silicon, guaranteed not to leak and they have nipples.” She handed me one after removing it from the box. “They feel very life-like, not hard at all.”“They cost more, but I think they‘re worth the extra money. They’ll last. If you buy cheap ones you’ll have to replace them.” “OH MY GOD! I’m getting an erection. How embarrassing if she sees it.” I turned slightly hoping to hide the lump in my pants. “Okay then, I’ll take them.”“Do you like the skirt?”“Yes, I’ll take that as well. Would you pick out a top to go with it?” “Why don’t you look at these, I have to lock the door, we closed a minute ago.”“Oh, should you be going? I don’t mean to keep you.”“No, no don’t worry about it, I just don’t want anyone else coming in. Take your time.”I picked out a blouse and sat it with the other things. The lights went out and the store became semi dark.She returned and picked up the blouse. “The red color will look good on you, but it’s too small. Take off your shirt and try this one on. Do you want shoes?”I removed my shirt and put on the blouse. She was right again. It would fit perfectly when I added the fake breasts. “Yes a pair of heels, not too high.” I had come a long way from the time I walked into the store. I was actually starting to have fun with her helping me. I imagined us trying on clothes together.”What size do you wear in a men’s shoe?”“Nine and one-half” I replied. My erection was full blown now. I cast an eye toward her she was bending over; her skirt was just covering her butt. I could see just a hint of her polka dot panties under the hem of her skirt.“That converts to ten and one-half in a women’s shoe, how about these?” She said as she turned toward me. I caught her eyes which fixated momentarily on the bulge in my pants. A sly grin crossed her face then disappeared just as suddenly as it had appeared.I took the proffered shoes from her hands. I was red again. ”May I try them on?”“Sure, in fact there is a dressing room over there. Why don’t you try everything on? Make sure it all fits.”“Oh, I don’t know.”“Come on, don’t be so shy, and remember I’m here to help you. I’m your doctor.”“Okay.”I went into the fitting room and took off my pants, jockey shorts and the rest. I put on the panties. My God I was hard! The bra was problematic. When I stretched the straps in back the tab slipped out of my fingers and came around and slapped me. “Ouch.”“Do you need help?”“I can’t get the bra fastened.”The curtain slid back. “Here let me help you.” She said as she entered the dressing room. I was standing there in women’s panties with an erection, trying to fasten a bra. How humiliated could I be? “Turn around. There you go. Now turn back around.” She took my shoulder in her hand and directed my turn. “Now let’s put your tits in your bra. She held up one of fake breasts, then pulled a bra cup out and inserted the prosthesis, and then she did the other. I just stood there hoping she wouldn’t notice my erection. “That’s better, do you want pantyhose or a garter belt and stockings.”“Pantyhose I guess.” She left briefly and returned with a pair of black control top pantyhose. “You’ll need to sit down to put these on.” I sat down and pulled the pantyhose up to my knees, then stood and pulled them up to my waist.She looked at me. “You look very cute, with the right make-up and a wig you could pass in public, except for the mustache. I’m afraid that would give you away. Put on the skirt and blouse and your shoes, I’ll get the tags and ring you up.” I finished dressing and picked up my pants and took my money clip out of the pocket. I had brought extra cash so I wouldn’t have to charge anything. Paranoia runs deep for the first time cross dresser. Emboldened by the twilight I stepped out of the dressing room. I thought I should be coming out of a closet. I admired myself in a full length mirror. She was right, I looked pretty damn good, except for the mustache. That made me look ridiculous. I would just look from my neck down. cI walked up to the cash register which was discretely hidden by a display. “How much do I owe you?”“Three hundred fifteen dollars and fifty two cents.”I handed her four one hundred dollar bills. She counted back the change and handed it to me. “I really want to thank you for all your help. Do you accept gratuities?”“No that’s fine. I love doing this, especially with a first timer.” She stepped a little closer to me and adjusted my blouse. She looked up at me through those sexy rectangular framed glasses. Jesus she could look so cute. I couldn’t resist I bent forward and kissed her on the forehead. She responded by putting her arms around my neck and finding my lips with hers. I opened my mouth and felt her welcome my tongue into her mouth. Her tongue flicked in and out then was full into my mouth, her mouth opening fully as I joined her in our oral explorations. She pulled back. ”Come with me.” she said cocking her head to one side and smiling coquettishly. She turned and led me back to what turned out to be the employee break room. We stopped in front of a couch. We embraced again and I kissed her deeply. I pulled her down on the couch with me. Her hand was pushing my skirt up. The sensation was delicious. So this is what is what it feels like. No wonder they like it when Irun my hand up the inside of their thighs. I accommodated her reach by spreading my legs slightly. I pulled her top down over shoulder exposing her red bra. I pulled the bottom strap up over her breast and kissed and sucked her nipple. Joy said “Oh.” Then she said it again only very drawn out this time, a low moan. There’s that whiskey tenor again thought. I pressed bahis siteleri my mouth onto hers and she responded with equal pressure. We were like two snakes trying to pull the other inside its mouth while their tongues dueled in a passionate dance. I wanted her breast. I pulled back from her mouth and took her exposed breast fully in my mouth; I caressed her nipple with my tongue. “Are you going to make me suck your cock?” she whispered in my ear. “Yes.”“Then say it, say it, say you’re going to make me suck your cock.”I caught her drift, she liked a little domination. “I’m going to make you suck Harry. I’m going to make you rub Harry on your face, I’m going to…”“Who the fuck is Harry?” She interrupted pulling her head back. “Oh, you two haven’t met.” I reached down and pulled my pantyhose and panties down. I took her hand and placed it on Harry. “Harry is the name of my dick. Harry, meet Joy, Joy this is Harry”“You named your dick? I kind of like it.”“I’m glad; I think Harry kind of likes you. He likes it when you grip him and stroke him like you are doing right now.” I reached up and pulled her top over her head. I looked down on her. One breast exposed the other still in the bra cup. I bent and began sucking her breast again. She sighed with a little “Hmmmm.”God her voice was sexy when she was enjoying herself. She was stroking Harry with one hand rubbing my ass with the other. I determined it was time to make my move.”On to Third Base men! Put on your man pants and grab some pussy!” The fact that I was dressed as a woman notwithstanding the whole man pants thing.It has been my experience that when attempting to seduce a woman it is best to go for the gold so to speak with one hand, while feeling a breast with the other and keeping her mouth occupied with one’s own. She can’t say “No.” with a mouthful of tongue being the idea.But first there was the matter of the bra. I made short work of it, being far more expert at removal than attachment. Both of her breasts were now free and I enjoyed sucking them. I reached down to put my hand between her legs. “What the fuck?” I said rising up. I had found her vagina was a dick. “You’re a fucking guy!” ”Oh shit, you really didn’t know. I’m so sorry, I thought with the clothes you knew.” Joy tried to pull away.“I’ve never kissed a man before.”“I’m not a man, I’m a woman trapped in a man’s body. Are you angry with me?”“No, I guess not. I was just surprised.”“Do you like what has happened so far?”“Yes, I guess so.”“Do you want to stop? I really didn’t mean to trick you. It’s just the way you were looking at me…””“Well, I was looking at you. I just thought I was looking at a girl. You really had me fooled.”“You didn’t know? This really is your first time. I thought you were being coy with me. So do you want to stop or not?”’ “Well I guess that depends on what we are going to do next.”She answered by grabbing my finger and putting it into her mouth and sucking on it. I kissed her breasts and ran my hands across her ass. She accepted my finger and began to suck on it greedily. I added my middle finger and Joy responded by tilting her head back. She moaned again deep and low.I whispered in her ear, “Take my blouse off. I want to feel like a woman.” She rolled over on her back so I was atop her straddling her with my legs and my butt resting on the lump in her panties. She reached up and started unbuttoning my blouse. I helped her shrug it off. My skirt was now bunched up like a sash around my waist. My pantyhose and pantie still pulled down exposing the now forgotten Harry. I reached down and caressed Joy’s breasts again. Then I began to crawl up her body until Harry was in her face. “I want you to suck him now Joy. Put him deep in your mouth and then suck on him.” I reached down and helped her put her shoulders on the arm of the couch so she was in a reclining position..“Exactly what I had in mind.” Joy took Harry in her hand and stroked him. The she put her lips on his head and began licking the bottom of the helmet. She sucked him gently very gradually taking his length in her mouth. Her hand found its way back to my scrotum, then over my prostrate. Then just as she gently touched my anus she took Harry deep into her throat. I rose up almost standing; I grabbed the back of her head pulling her onto me. She responded by probing my ass with her finger we moaned together. She continued sucking me changing from shallow to deep penetration. Sometimes pulling back and masturbating me, then guiding Harry down to her breast and tweaking his head with her erect nipple. She milked precum up to the Harry’s head and licked it off.“Hmmm. I like your precum. Do you like me?”“Oh god yes. I like you very much.”“Do you want to do more?” “I don’t know.”“Do you want me to help you?”“Yes, I think so.”iShe pushed me back and took my hand in hers and pushed it down to her crotch. I her flaccid penis in her panties; I massaged it cupping her penis and balls in my hand and gently squeezing. I got up and knelt down on the floor beside her. I continued to massage her penis with one hand and a breast with the other. I looked up at her face. Her eyes were closed, she was smiling and her glasses were slightly askew. I reached through the leg of her panties and eased her penis out. I went back to her mouth and kissed her again we joined together, our mouths hungry for one another. I went to her breasts and sucked each in its turn as I grasped her still flaccid penis. Then her hand was on the top of my head and I felt myself being ever so gently pushed down. I gave her no resistance. I left her breasts and began kissing her tummy, touching her tattoos with my tongue. Then there it was a flaccid penis staring me in the face. My hand was on the cock on a young man who was in part a young woman. It was now or never. I looked at it. I looked at her polka dot panties with purple lace trim. Then I looked at it again. I took it up in my hand, I massaged it. I bent down and took it in my mouth. I became a cock sucker. “Oh God, yes. Oh God I love that.” I opened my mouth fully, I greedily took all of Joy’s cock in my mouth I could feel her getting excited. My mouth was güvenilir bahis filling and I was now unable to hold her as she became erect. I began kissing her, licking her cock; I rubbed it on my bra. Then put her back in my mouth my lips on her helmet my hand reaching between her legs. She spread them eagerly as I slipped a finger over her panties and into her ass crack. She rotated her hips and rose up arching her back. “Oh yeah, that feels so good. I want you so bad.”I pushed her pantie leg aside and put my finger in her ass. I still had her cock in my mouth I pushed down until I thought I might gag. Then I pulled back and gently enjoyed her some more.“Honey I want you. I want you now. I want you in my ass.”I released her and she rolled over and got up on her knees. I got on the couch behind her and rubbed my face over her ass. I felt the nylon covering those two delicious mounds on my face. “I want you too baby; I want to be in you. We need some lube though don’t we?”“Well this is a sex store I think we can come up with something.” She reached into the cushion a pulled out a white tube.“Do you always keep that there?”“I stashed it when I went to lock the door.”“This was planned?”“I told you I had no idea. Besides I wanted you.”I took it from her. I pulled her panties down. I reached between her legs and masturbated her for a minute. I kissed her exposed butt cheeks then took some of the lube on my finger and started rimming her ass. I inserted the tip of my middle finger. “Oh yes.” she sighed and wiggled her as from side to side. I added more lube and pushed in a little further. Joy gave a gasp of pleasure and rocked back to take my finger for a little deeper penetration. I removed my finger added more lube to her ass and massaged her anus with two fingers. I inserted them both this time and again she gave a gasp of pleasure followed by a low moan.“Do you have protection?”“I’m clean and if you are I don’t want it.”“We’re on the same page then. Do you like it when I put a lot of lube in your ass?”“Yes, I love how you are playing with my ass.”“I’m going to put more lube in you now and I’m going to put my fingers in your ass. I’m pushing them into you now. Yeah baby I like to see you wiggle your ass while put my fingers inside you.” I began stroking in and out faster and faster. Joy cried out in ecstasy. I pulled my fingers out of her ass. I put lube on Harry and some more on her ass. “I’m going to fuck you in the ass now Joy. Do you want me to fuck you in the ass?”“Yes!”I slid Harry into her welcoming anus. It was ecstasy. It was so tight, so warm. I began to slowly move inside her. I rocked back and forth, moving slowly enjoying her ass. I reached forward and grabbed what I had thought was a leather necklace. I had just realized the ring was for a leash. I pulled back on the collar, not too hard. Joy moaned with pleasure. She eased herself forward and I followed her lead. I was now astride her ass, rolling on her beautiful butt cheeks. “Oh God Joy, I want to come.”“Yes come in me, I want you to come in me.”I released my orgasm in a spasm of Joy. (Okay you know I had to say that.) “Oh! Oh! Oh my God!” I was shuddering I was weak; I gasped for breath and nearly fell on top of her. I lay there, Harry in her ass, my fake tits pressed on her, my own breasts aroused by the pressure. I reached around and gipped her breast. I kissed the back of her neck.“Hmmm. That was good. Are you sure you haven’t down this before?”“You’re my first Joy.” I pulled harry from her ass, she rolled over, reached between my legs and pushed her finger into my ass.“Do you like that?”“Yes.”“Then come here.”Joy guided me as I rolled over. She pulled my pantyhose down over my butt. I felt the cool lube in between my ass cheeks and I spread my legs to better accommodate her efforts. Then I felt the insertion.“Hmm you are tight Honey, just relax. I won’t hurt you, don’t worry.”I felt my anus opening, accepting her finger deeper and deeper I felt her knuckle between my cheeks. She removed her finger and mounted me.“Are you okay?”“Oh.”“I’ll take that as a yes.”Then I felt her cock as it slip into my awaiting ass. I rotated my hips up; I wanted her deep inside me. “Oh yeah.”She was fucking my ass. I felt so good. I kept thinking “Please don’t come, I don’t want you to stop.” In and out, in and out; I was rolling my hips in time with her tender thrusts. “Is this what you want?”“Yes. I want you to fuck me. ”“Oh, I’m going to come.” I felt her stroke increase faster and deeper than before. My ass was impatiently awaiting her orgasm. Then it came. I felt so fulfilled, I had given her satisfaction. She started making all sorts of happy noises and I joined her. We formed a duet singing the sounds of pleasure. She took her penis out of my ass. Then she slid down beside me guiding me into her awaiting embrace.My mood suddenly changed from bliss to shame. She kissed me, but I couldn’t respond. I felt deeply ashamed of what I had just done.“Uh-oh. I know what you’re thinking, it’s okay, everyone feels that way the first time. The question is did it feel good?””You know it did.”“Then tell me, if Mother Nature hadn’t intended you to experience it, she would have made it hurt. Did it hurt?”“Yes but in a good way.” She was right. Her words had put me at ease again.Joy laughed and kissed me. This time I reciprocated. We lay there together for a while. Kissing occasionally and caressing one an others bodies. I loved the way my stockings felt when our legs shifted.Then it was over. I got up and changed back into my straight clothes. She put my new clothes in a bag, and opened the door. We kissed one last time and she bade me good-by. “Thank you Joy, I’ll never forget this. You were a wonderful guide.”“Are you sure you’d never done that before?” She said with a grin. I got into my rental car and drove back to my hotel. The next afternoon I was flying back home. I could still feel her cock in my ass. I took a drink from the flight attendant and eased my first class seat back. I closed my eyes, sipped my brandy and relived the night before in exquisite detail smiling at the thought of Joy. Knowing she would be the inspiration for many masturbatory fantasies to come. “Enjoying the flight Sir?”“Yes in a way. I was really just remembering last night, I had a wonderful evening.”“I’m glad. Would you care for another brandy?“Yes, I think I would. Thank-you.”
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