A sissy learns to dress up. The next step.
Even though my friend Cheryl was older, I felt very close to her and she became like a big sister to me. A free spirt, liberal and an extremely sexual creature, she didn’t hide her large assortment of sexy toys or her friendships with several Gay men. She would openly talk about sex and having sensed early on my special needs and desires, and even though I was very young, nurtured them instead of repressed them.
It all started out playful and fun. She started to dress me up. Putting make up on me and dressing me in pretty, feminine clothes and underwear, she never asked about me being gay or not. She just let me be me. Before long though, she began hinting, saying thinks like if you are every going to have a man inside you, you had better be ready. You had better open yourself up for him. Before I knew it, that lead to her having me bend over and her inserting vibrators and dildos into me. First small but progressively bigger. “If you ever decide you want to suck a man’s cock, you had better practice” She also had me licking and sucking realistic, cock like, dildos.
Cheryl even began taking me out in public dressed up. Usually shopping for make up or cute “girly” clothes and with each outing I became bolder, more comfortably with this new identity.
Cheryl even set up a “date” for me. She had a friend come over and take me to her bedroom. Not knowing if he knew I was really a boy, I was afraid he would discover the truth, but was thrilled and in exctasy to suck my first cock. Walking out of her bedroom that afternoon, lip stick smeared and the taste of his jizz in my mouth. I felt transformed.
The very next time I was at her place, eager for her to dress me up again, to have fun and be “girly” she asked if I like her friend to come back over. I felt my heart race and quickly answered “Yes!”
I got all dolled up, Cheryl gave me a tight, little mini skirt to wear but told me not to put on any panties. She put make up on me and soon her friend arrived. This time, I took him by the hand and lead him to her bedroom, eager to love his cock again. Cheryl laughed saying, “I guess she knew what she wants.”
Once inside, with the door closed. I moved to him. He was much bigger than I obviously, and my hands moved naturally to his crotch, rubbing his cock through his pants, I felt it harden and my excitement heighten. Undoing his fly, I felt felt his manhood and stroked him gently. As I began to move to my knees in front of him, he stopped me, turned me around and bent me over the bed. Nervous, but excited, I felt his hands slide the mini up and over my hips. I began to understand why Cheryl told me not to wear any panties.
Afraid he would see I was a boy, I was tense and clenched my ass together. When he said “relax baby” my nerves seemed to melt away and I gave myself to the moment. I felt his warm, lubed and fat cocks head against my opening, rubbing it gently. Then he pressed it inside me.
Even more wonderful than Cheryl’s toys, and although painful, it was pure pleasure having him sink deeply inside me. His hands on my hips, holding my waist as he slowly moved in and out. It was not only the full feeling of his cock in my ass that I found so amazing, it was the whole sense and act of being taken. Being used for his needs. A man’s baser, a****l needs. I felt my lower back naturally, instinctively arch, giving him total access, allowing him to go deeper. I didn’t even notice that my cock was now rock hard and leaking a silky, stream of pre cum. As his pace quickened, my cock began to dance up and down. When he started to pound me, my cock slapped against my stomach, edging me to orgasm. One long, slow almost achingly intense orgasm. “Yes, yes!” I cried out, surprising both of us with my passion and he gripped down hard into my waist and pounded into me deep and hard. I came without touching myself just as Cheryl had thought me, and cried out in exctasy just as he filled me with his seed.
Used and spent, I layed there for awhile, happy and satisfied.
”I think you are ready for the next step” Cheryl said to me the next time I saw her, only days later. “That was so hot, listening to you guys that afternoon!” she said, “I wanted to join in!” “Cheryl!” I said, almost giggling, somewhat surprised. “What!” she said, “”It sounded so hot, I played with myself outside the door!” She asked how long I could stay today, saying she had plans for us tonight. I made an excuse to stay out to my folks and told her I was all hers.
Sitting in a very feminine pair of bra and panties, we listened to music as she put make up on me, thick lip stick and a wig. I felt so girly and sexy. “You are going to need to hide yourself better” and took out a pair of thin, sheer, legggings. I slipped them on and tucked my cock and balls as best I could, the tight material holding them in place. In a slim fitting dress and low heels, she took me out in her car and drove to an adult bookstore miles away. “You’re ready to get a man on your own” she told me and with instructions on how to act and what to say, she had me step out and stand near the dimly lit entrance to wait for a man to hit on me, or for me to hit on a man. Cheryl parked off to the side. I felt better knowing she was near by.
Soon a man pulled up in a car near me and mentioned me over. Although I was expecting someone to walk up to me, I walked over to him, my slim young frame surprisingly girl like, he called me sweety. He asked if I would like to take a drive and in the most girly like voice I could muster, said, “Why don’t you just park over there and I’ll come sit with you” He smiled and parked in the back of the dimly lit lot. Knowing Cheryl could still see me, I met him there and got in. He was much older, around 40 or so I guess, balding and alittle bit of a tummy. He looked very much like a typical family man. I was so nervous, I didn’t want to talk for fear of him finding out I was a boy, maybe he knew already, maybe he didn’t, but I wasted no time and leaned over into his lap. Kissing the pant material at his crotch, my hands shook as I fumbled to undo his belt. He helped and I freed his swelling cock. Listening to Cheryl’s advice, I moaned softly as I licked his limp cock, watching it move as it harden, I was so turned on. I felt my own cock swell. It was uncomfortably and painfully hard, held up so tightly between my legs, but I did not dare to adjust it.
“Ohhh, that’s nice, sweety. That feels so good.” Hearing his encouragment, I lowered my wet, eager mouth onto him and he put his hand gently on my back and the back of my neck. His cock tasted familiar and wonderful, easily making me feel lusty and lost in the moment. Everything wonderfully and excitingly heightened, hearing and feeling his hot breath, feeling his chest rise and fall as my attention made his manly body tense, his cock twitch and throb, all for me. He eased himself back in his seat and his hand began to gently guide my mouth down onto him even further. “Mmm, baby, you’re going to make me cum” what wonderful words to hear a man say. Then, his release! He came so much! I struggled to accept it all. Swallowing as much of his wonderful seed as I could, and yet still some poured out the sides of my mouth. Feeling so much of his cum slid down my throat and fill my stomach, I really felt slutty and used. He needed this, obviously and I felt incredible to be able to do it for him.
Wiping cum from my lips and chin, I simply said, “Bye, baby” as girly as I could and got out. I felt intoxicated, high from the experience, I walked to Cheryl’s car and got in. I couldn’t help but have a huge smile. “Girl, that was so hot!” Cheryl said excitedly. “I could see the silhouette of your head going up and down on him!” “I played with myself the whole time!” she said then stuck her smelly pussy juice covered fingers in my face. So gross, I said laughing, slapping her hand away. “My cock was so hard the whole time” I told her. “Mmmm, I got so horny, I need to get fucked so bad!” she said, then looked at me and said, “Take your cock out” I needed to cum so bad too that I pulled down my leggings, letting my soft pre cum covered cock out. Cheryl moved over onto me, sitting on my lap. “I need a cock inside me” she said, grabbed my soft dick and rubbed it on her wet slit. The musky scent of her pussy filled the car.
Sensing it wasn’t going to happen, she asked “Do you want to pretend that I’m a boy” and squirmed her way to her knees and bent over. “Here put it in my ass” she said and all of a sudden I felt the urge take over. Her thin frame, her boyish body in the dim light. I thought about it being a classmates ass, a boy from gym class. I was rock hard when she reached behind her and guided my dick at her asshole and nature took over. I pushed my cock inside her, ran my hands over her ass and back and while imagining it was that boy, held her hips and moved my cock in and out of her tight hole. Somewhat secretly, picturing my cock entering that sexy boy, I felt my blood boil and my orgasm build. Cheryl had reached between her legs and rubbed herself to an orgasm while I fucked her ass, then filled her with my cum, my legs shaking and my body tingling.
I lost my virginity in her smelly, musky, pussy scented car that night. Right there in a seedy adult book store parking lot. A wonderful night of firsts for me and I would never be the same. It was the first time I had fucked someone, or more specifically, I first time I had done the fucking.
It all started out playful and fun. She started to dress me up. Putting make up on me and dressing me in pretty, feminine clothes and underwear, she never asked about me being gay or not. She just let me be me. Before long though, she began hinting, saying thinks like if you are every going to have a man inside you, you had better be ready. You had better open yourself up for him. Before I knew it, that lead to her having me bend over and her inserting vibrators and dildos into me. First small but progressively bigger. “If you ever decide you want to suck a man’s cock, you had better practice” She also had me licking and sucking realistic, cock like, dildos.
Cheryl even began taking me out in public dressed up. Usually shopping for make up or cute “girly” clothes and with each outing I became bolder, more comfortably with this new identity.
Cheryl even set up a “date” for me. She had a friend come over and take me to her bedroom. Not knowing if he knew I was really a boy, I was afraid he would discover the truth, but was thrilled and in exctasy to suck my first cock. Walking out of her bedroom that afternoon, lip stick smeared and the taste of his jizz in my mouth. I felt transformed.
The very next time I was at her place, eager for her to dress me up again, to have fun and be “girly” she asked if I like her friend to come back over. I felt my heart race and quickly answered “Yes!”
I got all dolled up, Cheryl gave me a tight, little mini skirt to wear but told me not to put on any panties. She put make up on me and soon her friend arrived. This time, I took him by the hand and lead him to her bedroom, eager to love his cock again. Cheryl laughed saying, “I guess she knew what she wants.”
Once inside, with the door closed. I moved to him. He was much bigger than I obviously, and my hands moved naturally to his crotch, rubbing his cock through his pants, I felt it harden and my excitement heighten. Undoing his fly, I felt felt his manhood and stroked him gently. As I began to move to my knees in front of him, he stopped me, turned me around and bent me over the bed. Nervous, but excited, I felt his hands slide the mini up and over my hips. I began to understand why Cheryl told me not to wear any panties.
Afraid he would see I was a boy, I was tense and clenched my ass together. When he said “relax baby” my nerves seemed to melt away and I gave myself to the moment. I felt his warm, lubed and fat cocks head against my opening, rubbing it gently. Then he pressed it inside me.
Even more wonderful than Cheryl’s toys, and although painful, it was pure pleasure having him sink deeply inside me. His hands on my hips, holding my waist as he slowly moved in and out. It was not only the full feeling of his cock in my ass that I found so amazing, it was the whole sense and act of being taken. Being used for his needs. A man’s baser, a****l needs. I felt my lower back naturally, instinctively arch, giving him total access, allowing him to go deeper. I didn’t even notice that my cock was now rock hard and leaking a silky, stream of pre cum. As his pace quickened, my cock began to dance up and down. When he started to pound me, my cock slapped against my stomach, edging me to orgasm. One long, slow almost achingly intense orgasm. “Yes, yes!” I cried out, surprising both of us with my passion and he gripped down hard into my waist and pounded into me deep and hard. I came without touching myself just as Cheryl had thought me, and cried out in exctasy just as he filled me with his seed.
Used and spent, I layed there for awhile, happy and satisfied.
”I think you are ready for the next step” Cheryl said to me the next time I saw her, only days later. “That was so hot, listening to you guys that afternoon!” she said, “I wanted to join in!” “Cheryl!” I said, almost giggling, somewhat surprised. “What!” she said, “”It sounded so hot, I played with myself outside the door!” She asked how long I could stay today, saying she had plans for us tonight. I made an excuse to stay out to my folks and told her I was all hers.
Sitting in a very feminine pair of bra and panties, we listened to music as she put make up on me, thick lip stick and a wig. I felt so girly and sexy. “You are going to need to hide yourself better” and took out a pair of thin, sheer, legggings. I slipped them on and tucked my cock and balls as best I could, the tight material holding them in place. In a slim fitting dress and low heels, she took me out in her car and drove to an adult bookstore miles away. “You’re ready to get a man on your own” she told me and with instructions on how to act and what to say, she had me step out and stand near the dimly lit entrance to wait for a man to hit on me, or for me to hit on a man. Cheryl parked off to the side. I felt better knowing she was near by.
Soon a man pulled up in a car near me and mentioned me over. Although I was expecting someone to walk up to me, I walked over to him, my slim young frame surprisingly girl like, he called me sweety. He asked if I would like to take a drive and in the most girly like voice I could muster, said, “Why don’t you just park over there and I’ll come sit with you” He smiled and parked in the back of the dimly lit lot. Knowing Cheryl could still see me, I met him there and got in. He was much older, around 40 or so I guess, balding and alittle bit of a tummy. He looked very much like a typical family man. I was so nervous, I didn’t want to talk for fear of him finding out I was a boy, maybe he knew already, maybe he didn’t, but I wasted no time and leaned over into his lap. Kissing the pant material at his crotch, my hands shook as I fumbled to undo his belt. He helped and I freed his swelling cock. Listening to Cheryl’s advice, I moaned softly as I licked his limp cock, watching it move as it harden, I was so turned on. I felt my own cock swell. It was uncomfortably and painfully hard, held up so tightly between my legs, but I did not dare to adjust it.
“Ohhh, that’s nice, sweety. That feels so good.” Hearing his encouragment, I lowered my wet, eager mouth onto him and he put his hand gently on my back and the back of my neck. His cock tasted familiar and wonderful, easily making me feel lusty and lost in the moment. Everything wonderfully and excitingly heightened, hearing and feeling his hot breath, feeling his chest rise and fall as my attention made his manly body tense, his cock twitch and throb, all for me. He eased himself back in his seat and his hand began to gently guide my mouth down onto him even further. “Mmm, baby, you’re going to make me cum” what wonderful words to hear a man say. Then, his release! He came so much! I struggled to accept it all. Swallowing as much of his wonderful seed as I could, and yet still some poured out the sides of my mouth. Feeling so much of his cum slid down my throat and fill my stomach, I really felt slutty and used. He needed this, obviously and I felt incredible to be able to do it for him.
Wiping cum from my lips and chin, I simply said, “Bye, baby” as girly as I could and got out. I felt intoxicated, high from the experience, I walked to Cheryl’s car and got in. I couldn’t help but have a huge smile. “Girl, that was so hot!” Cheryl said excitedly. “I could see the silhouette of your head going up and down on him!” “I played with myself the whole time!” she said then stuck her smelly pussy juice covered fingers in my face. So gross, I said laughing, slapping her hand away. “My cock was so hard the whole time” I told her. “Mmmm, I got so horny, I need to get fucked so bad!” she said, then looked at me and said, “Take your cock out” I needed to cum so bad too that I pulled down my leggings, letting my soft pre cum covered cock out. Cheryl moved over onto me, sitting on my lap. “I need a cock inside me” she said, grabbed my soft dick and rubbed it on her wet slit. The musky scent of her pussy filled the car.
Sensing it wasn’t going to happen, she asked “Do you want to pretend that I’m a boy” and squirmed her way to her knees and bent over. “Here put it in my ass” she said and all of a sudden I felt the urge take over. Her thin frame, her boyish body in the dim light. I thought about it being a classmates ass, a boy from gym class. I was rock hard when she reached behind her and guided my dick at her asshole and nature took over. I pushed my cock inside her, ran my hands over her ass and back and while imagining it was that boy, held her hips and moved my cock in and out of her tight hole. Somewhat secretly, picturing my cock entering that sexy boy, I felt my blood boil and my orgasm build. Cheryl had reached between her legs and rubbed herself to an orgasm while I fucked her ass, then filled her with my cum, my legs shaking and my body tingling.
I lost my virginity in her smelly, musky, pussy scented car that night. Right there in a seedy adult book store parking lot. A wonderful night of firsts for me and I would never be the same. It was the first time I had fucked someone, or more specifically, I first time I had done the fucking.
5 ani în urmă
