Turned Into A Sissy Boi

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Turned Into A Sissy BoiIt started innocently enough. I was spending another weekend with my girlfriend and we were in bed late one Saturday night. She had just cum and I was rapidly on my way there. I was on top pumping in and out of her. She snaked her hand back and started lightly brushing her fingertips around my butt-hole. I let out one moan, then another, and on the third one, I shot my load inside her. It was one of the best orgasms of my life!“Oh, you liked when I played around with your backdoor, huh?” she said a moment later with a teasing smile.“I sure did! It was great!” I responded. Looking back on it, little did I realize exactly where this was going to lead!My girlfriend Jenny was about 5’ 10” tall (one inch shorter than me when she didn’t wear heels), shoulder length dark brown hair, B-cup boobs and a killer ass! She was very pretty, and I thought myself quite lucky to be dating her. She was also four years older than I was.I’m 5’ 11”, thin, not much facial or body hair, and have a 5” cock. I was a little worried about the size of my penis, as I really wanted to please Jenny in bed. She always told me not to worry about it, as she was satisfied. Each time we made love after that one night, she always diddled with my asshole. First it was only around the rim. Then, she started putting a finger inside my ass, and then two. And, we were making love more often. I was in heaven! I’d make sure she would cum, and then she’d reach back and start playing with my eager hole. Always within a minute of her fingers penetrating my pucker, I’d explode. It was great!Jenny started insisting on my having an enema before bedtime. I didn’t argue that much. Besides, as the warm soapy water flowed up my fanny, she would gently stroke my erection. She was great at keeping me on the edge. Between her hands and the nozzle up my butt, I came close to cumming a couple of time. She would also tease me by moving the nozzle in and out. I would be moaning by the time the bag was empty and literally did anything she told me too once the water was expelled and she led me by the dick into the bedroom. Little did I know what was in store.I got to her place one evening, and she opened the door wearing a push-up bra, garter-belt, stockings, and a wicked grin.“I have an interesting evening planned for us, baby” she said. I just stared at her with a stupid grin on my face.She gave me a passionate kiss, then brought me into the living room, and stripped me. Grabbing my throbbing member, she led me into the bathroom. I immediately dropped to my hands and knees, naked butt held high in the air.“My, but you’re such a good boy”, she said with a chuckle. She smacked my bottom a couple of times before she lubed my asshole. I arched my back and pressed back against her finger as she slid it up in me.“You really like it when I fuck your ass with my finger, don’t you?” she said with a smile.“Oh yeah” I sighed. “I love everything you do to me honey!”“Good. Let’s clean out this nasty ass of yours. I have a special treat for you tonight.”“I can’t wait!”During that enema, Jenny played with my cock and balls and I came dangerously close to having an orgasm several times. She knew just when to back off though. She also gave me several smacks on my presented posterior telling me what a cute ass I had. With a final smack, she told me to use the toilet. Afterwards, she wrapped her hand around my penis and led me into the bedroom.She had me get on my knees with my face on the bed. My ass was positioned towards her. She told me to spread my legs a bit, and she started to slide a lubricated finger in and out of ass. I started to moan, and she chuckled.“That feels good, doesn’t it?” she asked playfully.:”Mmmm Hmmm” I moaned in response.“Then this should really feel good,” she laughed. I felt something press up against my hole. In another second, I felt this large object being pushed into me.“What the hell are you doing”, I said as I started to get up?I got a sharp slap on my ass.“Lie back down!” Jenny ordered. I did as I was told, and felt more and more of something being shoved up my ass. “Tonight, I’m the one who’s going to do the fucking” Jenny announced. “I’m going to fuck your ass with a strap-on, so you may as well try and enjoy it.”“But….” “Exactly! Your butt! The butt I’m currently fucking! I want to see if I can make you shoot your load by butt-fucking you! Now just kneel there like a good boy and enjoy.”I did as I was told as Jenny slowly pushed the dildo into me. She then drew it out just as slowly. The next in and out motions were just a bit faster. It took her a minute or two before she got into a nice rhythm.When the strap-on first entered my butt, my canlı bahis şirketleri cock began to soften. However, as she started to fuck me, it grew stiff again, and I had to admit that I was really enjoying it. I began to push my ass back against her. I started to moan again.“That’s it baby. It feels good when I fuck your ass, huh? You like it when I fuck your ass, don’t you?” I really did! The soft plastic cock moving in and out of my bottom felt strange yet wonderful. Jenny was plowing my butt harder and faster now. My dick was hard as a rock. “Cum for me baby! Cum for me baby! Shoot like a good boy!” Jenny repeated this over and over and started smack my ass cheeks while thrusting the strap-on in and out of my willing butt. I finally reached the point of no return and let out a load groan as I came all over the bed. Jenny buried the strap-on deep in my ass and held it there while I shuddered in orgasm. She briefly pulled out and unbuckled it, then shoved it back into my ass. She told me to stay where I was. She grabbed a paper towel and wiped up my sperm. Then since I was at the bottom of the bed, she lay down in front of me, legs spread wide. I didn’t need to be told what to do. I started eating her out with my dildo-filled butt sticking up in the air.Sex for the next few weeks consisted of me getting my rump reamed in all sorts of positions around her apartment with different sized strap-ons and dildos. I started wearing rubbers so that I wouldn’t get any of my sperm on furniture or rugs. Occasionally, Jenny would play with my cock a bit, but the more she screwed me, the less she touched me. Having something shoved in and out of my ass was enough to get me off. I then brought her off orally.We were out at the mall one day, and she took me into Frederick’s. Jenny had a lot of stuff from them, and looked fantastic in everything. She picked out a lacey red garter belt, a pair of black stockings, and some lacey crotchless panties. “You’ll look great in that outfit,” I told her. She just smiled.When we got back to her place, she told me to strip which I gladly did. After my enema, Jenny stripped also and took me into the shower. I thought we were going to make love in there, but Jenny had other ideas. After washing me, she took a razor and shaving cream, and announced that she was going to shave my pubic hair off. At first, I weakly protested but then gave in to her demand. She however insisted, so I spread my legs as she removed all the hair from my cock and balls. She then told me to turn around and bend over. What little hair on my ass also departed. We then out of the shower, dried off, and she led me into the bedroom. On the bed were the items she bought earlier in the day.“This outfit is for you. Put it on.”At first, I was too shocked to say anything. I couldn’t believe it! She actually wanted me to wear panties and stockings?“Jenny! I’m not going to wear that!”“Oh yes you are” she said quietly. Her hand, which had been around my cock as it usually was now moved to my hairless balls. “But Jenny…” She smiled at me, said nothing, and she started to squeeze my nuts. “Okay! Okay! I’ll put it on! Please stop squeezing!”“I’ll help you dress this time. I want you to get it right.”I put on the garter belt then the stockings. Jenny helped me get them straight and showed me how to clip them. The panties went on last.“You look so cute!” Jenny said, as she looked me over.“I feel ridiculous!” “You’ll learn to like it. I enjoy fucking you and you like getting fucked. I just thought you should look the part. Now, come over here.”Jenny sat down on the edge of the bed. I stood beside her.“Lie down across my lap.”I did as I was told. She had get into this position about a week ago in order to grease up my butt hole. She reached down and grabbed my right arm and twisted it on my back. I suddenly knew that she wasn’t about to do any greasing of any holes.SMACK! Her hand came down on my panty-covered bottom. Crack! Her hand came down sharply again, this time on the other cheek.“Jenny, please stop! You don’t need to do this!”“I think I do. When I tell you do something, I expect you to do it without arguing or whining about it. Maybe if I heat up your pansy ass, you’ll learn to do what I say when I say and how I say.”I knew that pleading was useless, so I resigned myself to getting a spanking dressed like a sissy. Jenny did not disappoint. Her hand came down hard and fast on both cheeks. I felt my bottom starting to heat up. I also felt my cock getting hard. The more she spanked, the harder it got.“Stand up” she ordered after a few minutes. I stood there with my bobbing erection inches from her face. “Hmmm. Looks like we found mobilbahis something else that you like” she said as she fondled my dick. I moaned slightly as pre-cum oozed out.She pulled my panties down and had me step out of them. Then she placed me back over her lap with my cock firmly between her legs. She reached over to the nightstand and grabbed her plastic hairbrush. CRACK!!! CRACK!!! CRRACKKKK!!!!The brush stung a lot more than her hand did, but I did nothing but yelp at first. Jenny covered my whole ass with redness and soreness. The spanks were hard and steady and it felt as though my butt was on fire. But at the same time, I was ready to explode as my cock was rubbing against her bare legs. After five minutes, I was half crying in pain and half moaning in pleasure. Then it happened. I arched my back and exploded all over her legs.“I knew it! I just knew it!” Jenny exclaimed as she saw my back arch and felt my cum on her thighs. She paused spanking me while I shuddered in orgasm. After a minute, she had me get off her lap. My ass felt hot, swollen, and very, very sore. She spread her legs and ordered me to lick my cum off her legs. After that, she lay back on the bed and ordered me to eat her. She had an orgasm in a few short minutes.Sex changed for me after that night. I no longer fucked Jenny. I used my tongue and got her off orally. She kept me dressed as a sissy slut in garter belts, stockings, and all types of panties. I was required to keep my bum very clean, and to keep my body hairless. I wore the frilly lingerie under my “outside” clothes, and immediately stripped down to them when I entered Jenny’s apartment. Spankings became more and more frequent but with rare exceptions, I came each time she reddened my rump. In addition, she used several dildos and other objects to fuck my willing bottom, and I squirted each time that happened also. She began to “expose” me to different people. Once, wearing red stockings, red and white crotchless panties, and having a pink ribbon tied in a bow around my hairless balls, she made me answer the door when she ordered pizza. The pizza delivery boy just stared in shock at my outfit, and my face matched the color of my stockings. Jenny saw the whole thing and could hardly keep from laughing. I wore the same outfit a week later when she again ordered pizza. This time, an older woman delivered it. She started to laugh immediately.“Nice bow, sissy ” she said.Jenny appeared at the doorway and the delivery woman congratulated her on my outfit. As I was paying her, embarrassed as anything, I dropped one of the bills. Jenny ordered me to turn around and pick it up, which gave the woman a bird’s eye view of my recently spanked ass. “Glad to see you keep him in line” she laughed.“I’ll need to give him a few more whacks since he was clumsy” Jenny remarked, “Unless of course you want to. After all, he was handing you the money.”“Sure. Why not? I’ll beat his ass a little” the woman chuckled. I could hardly believe my ears! Jenny was inviting a total stranger into her apartment to spank me!The woman had me bend over and grab my ankles in the middle of the living room. Jenny showed her a few of the things she normally used on my fanny. The woman chose the wooden hairbrush and gave me about a dozen hard smacks with it. Both women laughed as I turned around after the spanking with my dick sticking straight out at them. Jenny explained that I enjoyed getting spanked as well as having my butt hole explored. My face turned redder than my behind.“Honey, some advice” said the woman after hearing all about my quirks. “Keep this one around for laughs but get yourself a real man with a real cock.” She pointed right at my little stiffy and said, “This one can’t be enough for you.” After a few weeks, Jenny announced that were going to have company for dinner one evening. During this time, I had answered the door numerous times dressed in slutty outfits. A few people were surprised, a few laughed. A lot of them looked at me in disgust and made loud insulting remarks. One or two guys thought I looked sexy in my outfit! Jenny took great pains not only with her appearance that evening but with mine as well. She made sure I was completely hairless and smooth, super clean inside and out, and that my outfit was perfect. I was dressed in red fishnet stockings that left my ass and crotch areas completely bare and accessible. I had a black thong, the front of which had tiny bows on it. A pair of black high heels and a small white lacey apron completed my outfit.Jenny had on a long low-cut dark blue dress with a small gold necklace and earrings. Her hair had a slight wave to it, and she mobilbahis giriş also wore high heels. She looked lovely and I told her so. She smiled. “This is a big night for both of us” was all she would say.The doorbell rang, and I went to answer it. When I opened it, there stood a tall well-built handsome blond man. He looked to be in excellent shape without being muscle-bound. “Hi. Jenny told me all about you. Nice outfit.” He said with a smile.I really didn’t know what to say. He sounded sincere!“My name is Richard. May I come in?”“Yes. Please” I stammered.As the door closed, he put his arm around my waist and we walked into the living room. Jenny was there with a smile on her face. Richard smiled back and held out his other arm. Jenny sided up next to him, and they kissed deeply. I was going to untangle myself and quite simply leave and not return. Jenny had found someone else and I wasn’t needed anymore. Before I could move, Richard ended his kiss with Jenny and turned towards me. His mouth found mine and he began to passionately kiss me! I was too surprised at first to do anything. But, that lasted only about two seconds. I started kissing him back. Jenny’s hand started stroking the front on my panties and I was rock hard in seconds.“Why don’t you get all of us dinner and Richard and I will explain while we eat,” Jenny suggested. Richard sent me into the kitchen with a playful slap on my ass.Over dinner, Jenny explained that she was never really satisfied with my small penis during sex. The past couple of months were spent in her exploring what sexual practices she did enjoy with me. She found out that she was a basically dominant person, while I was a true submissive. “I honestly enjoy dressing you up like a sissy, fucking your little bald butt, and spanking you,” she admitted. “And, I know you like it too. You cum each time I fuck or spank you.”“Richard is bi-sexual in case you didn’t know, and he has a beautiful 8 inch cock! Big and thick and very satisfying! He likes to fuck girls and boys, and get his cock sucked by both. He’s not a true submissive like yourself, but he does take orders from me very well.”“I thought the three of us would be very happy together. Richard takes care of fucking me, you take of both of our oral needs, and we take care of your submissive needs.”I couldn’t say anything for a minute. I looked into both of their faces. Jenny had it all planned out, and the more I thought about it, the more I realized that she was right! I still didn’t say anything, but I didn’t have to. Jenny saw the look on my face and gave me a big smile and a kiss.“Clear the table and meet us in the living room afterwards”, she ordered.When I came into the living room, they were both naked sitting on the couch and kissing each other passionately. Without breaking the kiss, Jenny spread her legs and pointed at her pussy. I immediately ran over, dropped to my knees and started licking her juicy cunt. After several minutes, she told me to stop and start sucking on Richard’s cock. And what a cock it was! Long, thick, and pointed at the ceiling, Richard was well endowed indeed! I had never sucked on another man’s dick before, but I suppose I was a quick learner, because after a few minutes, Richard started to moan.“Along with everything else, you’re s natural-born cock-sucker!” chuckled Jenny. I just kept bobbing my mouth up and down on Richard’s shaft.Jenny told Richard to start fucking her, and warned me not to cum. I was to get behind them and use my tongue on Richard’s cock, balls, and ass. It was difficult for me to even get close as his cock thrust in and out of Jenny’s pussy. She moaned in sheer delight and finally had a long shuddering orgasm. Richard thrust even faster in and out of Jenny until he groaned and shot his load deep inside her.They both lay still for a minute or two, and then Jenny asked Richard how well I licked his balls. Richard replied that I didn’t do a very good job at all. I remained kneeling where I was. They both sat up and Richard pulled me across his knees. “What a sweet, smooth little round ass you have”, he said softly as his hand rubbed over every inch of my upturned bottom.CRACK! The first smack was a hard one. The second one was just a bit harder. By the fifth spank, Jenny had positioned her freshly fucked pussy in front of my face. I moaned and started licking and sucking her. Richard did not have to spank me too long before my stiff little dick exploded all over his legs. Of course, I used my mouth to clean them up.These days, I wear lingerie exclusively and take care of all the housework and cooking. Jenny and Richard both work, and I wait on them hand and foot when they get home. I don’t get to fuck Jenny anymore, but I service them both orally, and love the feeling of Richard’s cock pounding in and out of my well-spanked ass whenever Jenny has her period. Everyone concerned likes the arrangements, and I am a happy little sissy boi!

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