Terry Gets It In The End

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Tem 12, 2022 // By:analsex // No Comment

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The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and some faceless guy was fucking the shit out of me. I learned to dance and I loved the way my skirt flew up and exposed my panties but dancing like that wasn’t the way I had to dance at the school mixers. I had to dance like a boy, which was easier because all you had to do was move a little and shuffle you’re feet while the girl did all the fun stuff. There was one girl that asked me to dance after seeing that I wasn’t really into this whole “mixer” scene. She was a very good dancer and very pretty and I was astonished that she didn’t have a dozen guys wanting to dance with her. We danced to a few songs and then sat together and talked when we finished. I didn’t have much experience with girls but she was very easy to talk to. “You’re a good dancer, Cheryl,” I said. “You’re not so bad but you need to relax and feel the music. I think that you could really dance if you let yourself go.” “But it’s kind of embarrassing,” I told her. “I’ll tell you what. You dance the next song, and I mean really let go and I’ll tell you something embarrassing about me.” “Really? What could you have that’s embarrassing?” “Dance with me and I’ll tell you. You’re a nice guy, not like the others. All they want to do is get in your panties,” she said and laughed. “What makes you think I don’t want the same thing? “You’re different. I can feel it.” “Oh?” “Yes. Now come on and dance with me.” We danced and I let myself go, using all the girlie moves I’d been doing in my room. Well, a lot of them anyway. “I knew you had it in you,” she laughed as we sat down again. “But doesn’t it make me look gay?” “So what if it does? You had more fun this time. Right?” “Yea, I guess I did. So now tell me something embarrassing about you.” “Okay,” she replied and leaned closer to me. “I’m not wearing anything under my dress. No bra, no panties, just me.” “Really? Cool,” I replied and laughed. We danced to a few more songs before leaving. I’d somehow worked up enough courage to ask her out for something to eat after the dance. Later, when I drove her back to her car we kissed, and I mean we really kissed -tongue and everything. We dated the entire senior year, going to movies, dances, dinner, and whatever. Then one night, sitting in my car at the local make out spot, we were kissing and I let my hands do some roaming. I found her breasts and gently began teasing her nipples. Soon enough my hand was inside her blouse and directly on her nipples, “That feels so good,” she moaned and ran her hand across the slight bulge in my pants. Before I even realized it my lips had moved to her nipples and I was sucking and running my tongue all across them. While I was busy with her nipples she unbuckled my belt and open my pants. She had me so worked up that I had forgotten I was wearing panties until she brought it to my attention. “Nice panties,” she said as her hand slid beneath the satin. “Huh? Oh damn,” I exclaimed just as her hand found my throbbing cock. “I like it,” she grinned and leaned down to take my cock in her mouth. I couldn’t believe how good it felt. Her mouth was so hot and wet and her tongue was giving me fits. It didn’t take long before I blasted my load. “Oh damn, Cheryl. I’m so sorry! I couldn’t help myself!” She smiled at me and said, “That’s okay, Terry. I wanted it to happen. And when I found that you were wearing panties, I just had to do it.” Then she kissed me. I could taste my cum on her mouth and it was very exciting. Of course, I’d tasted my own cum many times but this was more exciting. After some maneuvering I had her laying back on the seat and her legs spread wide. I lifted her skirt and saw her bare pussy. I knew I couldn’t fuck her, not that I really wanted to do that sort of thing but I could give her pleasure in the same manner in which she’d serviced me, so I bent down and kissed her, gently licking her. “Oooo, Terry!” she moaned. Her moans told me I was doing something right so I continued. I’d read where girls really liked the way other girls ate pussy because the were slow and gentle, so that the way I did it as well. While I licked her pussy and teased her clit my hands tormented her titties, twisting and pinching her hard nipples. “Oh! Oh! Oooohhh, baby! Yyyesss! Damn you can eat pussy!” Then she raised her hips and shook herself at me, cumming hard against my mouth and screaming loudly. At that moment a copious amount of her fluids blasted out, surprising me and her. I thought at first that she had pissed in my mouth but it didn’t taste like piss. Yes, I had tasted piss after seeing images of others drinking it. I decided that since she had just cum, it must be the female equivalent of semen. “Wow! I certainly wasn’t expecting that!” “So now we’re even,” I laughed. “Well you feel free to do it again whenever you like,” Cheryl giggled. “But promise me one thing. Promise me you’ll keep on wearing panties.” güvenilir bahis “Don’t worry, I will. I promise.” For the duration of the school year Cheryl and I continued our oral sexual assaults on one another whenever we could find the opportunity. She really liked me in panties, which, of course, I still wore every day. And it was one afternoon in her bed when we were both naked that she saw my toe nails were painted. “Mmm, panties and painted toe nails,” she smiled, “very sexy. What else do you do that’s feminine?” “I, um, I sometimes like to dress like a girl. You know, skirt, blouse, stockings, bra, the whole nine yards,” I blushed and awkwardly confessed. “Really? Cool! I guess that explains why you haven’t tried to fuck me, not that I’m complaining about what you are doing to me,” she laughed and kissed me deeply. We talked on and on, and I eventually told her about some of the erotic fantasies I had when I was all dressed up. Cheryl seemed to be extremely interested in them and then confessed to me that she also had some fantasies going on when I was eating her, like me really being a girl going down on her. One thing lead to another and I was soon promising to dress up like a girl for her when we could find the time. One week before graduation she drove to my house and I was waiting for her arrival in a pastel blue mini-skirt, white satin blouse, black stockings, garter belt, red satin panties, bra and heels. Not only was I dressed but I also had on makeup and wore painted finger and toe nails. “Holy cow! You look great, Terry,” she said immediately upon seeing me. “You make a very pretty girl!” She took out her phone and took several pictures of me. She had me posing for her everywhere, living room, bedroom, kitchen, even outside in the back yard, and took pictures of me in all sorts of positions from nice to risque to even some that left no doubt that I was born male. “This is really making me hot, Terry,” she gasped. “Yeah, me too,” I laughed. After that it wasn’t long before we were in my bed and I was extremely busy licking her flooding pussy. Cheryl was completely naked and I was still mostly dressed. But being dressed made me act more like a girl, which drove her wild. I was persistent in my activities, eating her slowly but with more passion than I thought I possessed. “Yes! Yyyesss! I’m cumming again. Oooohhh, Terry, I’m cumming! I’m cumming!” Cheryl screamed, driving her pussy harder and harder against my lips. After about a million orgasms, she pushed me away and then pulled me up to lay beside her while she caught her breath. “Oh damn, baby, you’ve got to dress up when you eat me next time. That was absolutely wonderful! Will you? Will you be my lesbian lover?” “I can do that,” I replied. “You’re a real keeper, baby,” she mumbled as she drifted to sleep in my arms. We slept like this for an hour or so and when we awoke it was almost time for my mother to arrive. Cheryl quickly pulled on her skirt and top and then began brushing her king brunette hair. “Put your jeans and shoes on over your stockings, babe,” she said urgently. “I’ll brush your hair while you wash off your makeup and take off your fingernail polish.” As quickly as I could I did as she said and then slipped on a black t-shirt without even thinking about my bra. When Cheryl mentioned it I put on a leather vest to hide the telltale signs of my bra. We barely had enough time to get to the den and switch on the television before Mom arrived home from work. “Hi kids,” she said as she swept through the room on her way to her own room to change. “I think we could have been sitting here stark naked and she wouldn’t have noticed,” Cheryl laughed and ran her hand over my crotch as she leaned in to give me a kiss. Since Cheryl was staying for dinner we got up and began preparing the meal, something I had been doing quite often. After she had the table set Cheryl said, “You’ll make someone a good wife someday.” “Wife? Do you think I’m gay or something?” I asked, trying to sound serious. “You may not be gay, babe, but you’re pretty damn close,” she replied with a laugh. “Not that it matters a whole hell of a lot to me whether you are or not. I love you just the way you are.” “And I love you, too, Cheryl. By definition, doesn’t that mean I’m not gay?” “I believe the correct term is latent homosexual,” she replied. “You’ve got to be kidding. Right?” “No, I’m not. But even if you’re as queer as a three dollar bill, I don’t care, baby. You’re kind, definitely gentle, sweet, romantic, considerate. In short, Terry, you’re wonderful.” Her compliments lessened the the impact of her earlier words, but in my heart, I knew she was right. Mom appeared in her usual attire, which wasn’t much, just a t-shirt and panties. We say and ate and talked for quite a while until it was time for Cheryl to go home. I walked her to her car and we kissed for quite a while. “After what you did this afternoon I can’t just leave you high and dry,” she whispered and opened my jeans. After a short time she had my dick out and was sitting in her car sucking me while I stood beside the car. The open door shielded what she was doing from any car passing by. She was very good at what she was doing and had me moaning and groaning in no time. güvenilir bahis siteleri “Oh Cheryl, that feels so damn good! Oh baby, you’re gonna make me cum! Oh! Oh! Oh! Here it cums baby, I’m there! Oh fuck! Oh fuck!” The last few words were unintelligible because I was draining my balls into her greedy mouth. When I was finished she stood and kissed me deeply, give me all the cum she had in her mouth, which I accepted and swallowed. “I bet you wish that was another man’s cum you just swallowed. You dream about that. Don’t you, Terry.” “Sometimes, yes,” I admitted. “We’ll work on that,” she giggled. ”Work on what?” “We’ll work on finding you a cock to suck.” “Yeah? How about we work on finding a girl to eat your pussy?” “After we find a man for you.” “A man?” “Of course. Now I can sort of break you in, you know, with a strap on dildo, but I really think you’d prefer a real man with a cock that cums in you.” “You really want me to suck a man’s cock?” “You’ll love it, baby. And then when you get fucked, well, you’ll really accept your gay side more than ever.” “Whatever you say,” I agreed dubiously. Truthfully, what she said got me to thinking. I knew my fantasies were of a gay nature, so maybe that’s what I really wanted. And there was also my obsession with crossdressing and my desire to look and act as feminine as I possibly could. There was also the fact that when I had the perfect opportunities to fuck Cheryl my cock had mysteriously lost all interest and went limp. “Tomorrow we’re going to put some things to the test. From what I’ve seen of you all dressed up, I think you can easily pass as a girl, that being said we’re going to spend the entire day as girls. We’ll do some shopping, eat lunch and maybe do some people watching. It’ll be great!” “Go out? In public? As a girl? I don’t know about that.” “Oh come on. It’ll be so exciting!” I had to admit that it would be very exciting, and it was something I’d secretly wanted to do for a long time. “What if someone figures out I’m not a girl?” “So what if they do? It’s very doubtful anyone would, and if they did they wouldn’t care one way or another. Most people are too busy with their own business to worry about whether or not that pretty girl is a guy.” “Okay, I’ll do it.” “Cool! I’ve got a pair of silicon falsies at home. They’re not real big but they have a little bit of weight to them so they’ll move and feel like real boobs. I’ll bring them over in the morning. So you just be dressed and ready to go around nine.” “Don’t worry, I’ll be ready. Those falsies sound very nice. Thank you.” Before going to bed I took a long bath, shaving my legs closely, before taking care of my pubic hair and my arm pits. Slipping into a pair of yellow bikini panties and my bathrobe, I left the bathroom and nearly bumped into my mother. “Watch out, Terry,” she laughed. “Oops! Sorry, Mom.” I knew if I just rushed around her and went up to my room she’d wonder what was wrong and question me all night. So instead I told a little of tomorrow’s plans. “Cheryl and I are going to the mall tomorrow. She’s picking me up around nine so I thought I’d get a jump on getting ready.” “To the mall, huh? Well don’t get too carried away,” she laughed. “Oh no, just a couple of things,” I giggled, not telling her those things would probably be a skirt and blouse and maybe another pair of heels. “Oh, be on the lookout for a new swimsuit. That old one of yours looks horrendous. You’ve had it for how many years? Four? Five? Anyway, get a new one. Here, take my credit card and use it for the swimsuit. And for Pete’s sake, get a good looking one this time; something with some color to it.” “Okay, okay,” I answered, “How about if I look for hot pink?” I was wondering how I could pick out a male swimsuit while all dressed up. This was something, I decided, I’d have to talk to Cheryl about. “Hot pink would look good on you,” she smiled. “It goes nice with your pink toenails.” “Huh?” I looked down at my toes and realized they were still painted and I wasn’t wearing anything to hide them. “Honey,” Mom laughed, “did you honestly think I didn’t know about you dressing like a girl when I’m not here? I’ve known for years. I knew when you were a little boy that you weren’t like the rest. So you see, crossdressing isn’t a surprise to me. The only thing I’m not sure about is whether or not you’re gay.” “Mom! I’ve never been with a guy!” “Ah, but I’d be willing to bet that you would be with a man if the opportunity arose. And when you finally do it, and mark my words, you’ll be dressed up like a girl.” The blush in my face was enough answer for her. There was really nothing I could say. “With all this being said, I’d like to see you dressed up. I think you’d make a prettier girl than you are as a nice looking boy. What I mean is, as a boy you look kind of fragile but I think that as a girl you’d be cute and petite.” “Do you really think so, Mom. I mean Cheryl has said the same thing.” “Has she seen you dressed?” “Well, yes, she has.” “And what did she say?” “She really liked it,” I replied, excitement in my voice, “She took lots of pictures of me with her phone.” “Oh? Phone pictures, huh? I’ll tell you what. You have my credit card so go ahead and get a decent digital iddaa siteleri camera while you’re out shopping.” When I got up the next morning I was as nervous as a cat on a hot tin roof. Somehow I got my makeup on and my nails painted to match my toes. After slipping on a pair of white satin bikini panties and a bra, I looked in my closet for something to wear and decided on a baby blue sleeveless A-line dress with a scalloped hem. Before the dress I put on a pair of nude pantyhose and then slipped the dress over my head. I chose a pair of white sandals with ankle straps and three inch heels and strapped them onto my dainty feet. Finally I pulled out a greyish purse and loaded it with everything I might need during the day, extra lipstick, a compact with powder, my wallet with Mom’s credit card, my debit card, driver’s license, cash, keys, cell phone, and even a tampon. Now I was as ready as I’d ever be to go out and face the world. Cheryl arrived and handed me two boxes which held the falsies she had bragged about. Taking them from their boxes, she helped me slide them into the cups of my bra. She was right, their weight did feel good and natural. Twenty minutes after she arrived we were driving across town to a very nice mall. I had to admit that the walk from the house to her car had felt exhilarating. On the way I told her about my conversation with my mother the night before. “So your Mom knows about your crossdressing and thinks you’re probably gay, huh? Cool! Well that changes everything. I think we should get the camera first and I’ll use it to document your first day out.” She pulled into a huge electronics discount store and parked. “Ready, lover?” “As ready as I’ll ever be,” I grinned and opened the door. We walked into the store and I felt like every eye was on me but I kept my head up high and walked as though nothing was out of the ordinary. “Just walk like you own the place, Terry. No one is going to say a word,” Cheryl said encouragingly as we entered the store and walked down the main aisle. By the time we reached the camera department I was feeling more at ease. No one had said or done anything out of the ordinary. In fact, I felt as though I’d been accepted as a real woman. The camera we chose was pretty neat. You could set it to take any number of pictures automatically as well as taking videos. The memory card was huge but Cheryl insisted on buying a spare. We picked out the camera, a docking unit for downloading to a computer, spare memory card, a car charging unit, as well as a tripod. I gave the salesman the credit card and then signed the receipt. He took it all in stride and thanked us for shopping. My first venture into the real world as a girl had gone off without a hitch and my confidence soared. It had been lots of fun and I decided that even if they knew I was a guy in a dress they weren’t going to say anything for fear of losing a sale. Before leaving the parking lot Cheryl plugged in the camera to charge. “So how do you feel about getting out, now that you’ve conquered the first time?” Cheryl asked as she began driving. “I liked it,” I replied, “and it wasn’t as awful as I thought it would be.” “Then you’re going to love going to the mall. In fact, I may have a surprise for you.” “Oh? Well just keep it safe and sane,” I laughed. Once we arrived at the mall and made our way inside, Cheryl began taking picture as we did some window shopping. She even had me stop and do some posing for her right in the middle of the mall. But as we moved along I became more and more comfortable to the point where I didn’t even think about the way I was dressed. Everything seemed quite natural to me. We went into one of the stores and Cheryl insisted that I try on a few dresses as well as some skirts and blouses. I did and modeled them for her and she took pictures. She even came into the dressing area and took pictures of me changing.I was trying on swimsuits and she was still taking pictures of me changing and then modeling. I tried on several one piece suits and then she started handing me two piece ones. When I tried on a skimpy little bikini I fell in love with it, especially since it was hot pink. I decided that this is one I had to have. I looked forward to getting a tan in it and seeing the tan lines it would leave behind. When we left that store I had three bags of goodies. We made our way to the food court where we ate lunch and did some people watching. At first I watched the girls and women walking past to learn more about how to carry myself. Then my eyes started wandering to the guys and was impressed be a few of the nice asses I saw walking by. I couldn’t help but wonder about the size of their manhood and found myself getting a slight erection. “Okay, girlfriend, let’s get going. I need to go into ‘Les Femme’ and check on something with the boss.” We had to go to the other end of the mall to get to the store she worked in. While she went and talked with her boss I was left in the lingerie department. Looking around I found the prettiest nighties and, of course I just had to have one. I picked one that had sheer black panels on the sides, back, and tummy with blue satin insets covering all the important places. Cheryl returned and she was smiling. “Now for your surprise. The store needs another girl to help out in the shoe department. All you have to do is fill out an application and the job is yours. Well, after you interview with the boss. Of course, that means coming to work all dressed up.

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