Richard the Sissy Learns Community Service
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A Young Sissy Learns To Dress Up. free porn video
When I was very young a found my mothers friends Playgirl magazine. Curious, I nervously looked through the pages. Although, I didn’t know what my feelings meant or how to act on them, I knew I was drawn to the photos. I stared at them, finding the images of the naked men incredibly appealing. I remember the centerfold, he was tan, perhaps arab or hispanic. He had a hairy chest, hairy legs and a thick dark pubic mound over his hanging, dark skinned cock. Laying on his side, his thick, vein covered member dangled over his full, firm ball sack. I thought he was beautiful, and like that my horizons were broadened.
Before too long, I began exploring. Playful, seemingly innocent games with friends, like seeing who’s dick was bigger, or one looks this way what does yours look like. But for me, I knew and felt a deeper urge. I wanted to touch their cocks, I wanted to stroke their cocks. In later years, my lust and desires only became stronger. My desires to pleasure, love and worship cock, so strong, my urges and needs to feel submissive and used overwhelming. Even if I didn’t fully know or understand it. I had a few encounters with other boys, mostly pretending to be clumsy and drunk, afraid to show my true desire to just fall to my knees and make them cum.
It was at my my first job that I met a co worker named Cheryl. Older, Cheryl was nice looking but not beautiful. Thin framed, with long, dark hair, usually in a pony tail and bangs cut straight across her forehead. Almost from the start, she recognized something in me. She would make little comments and questions about if I found a certain boy attractive or if I wanted to see that guys cock. But she was never judging, never condensending. I began to spend a lot of time with Cheryl she was easy to like and easy to talk to.
It started out just for fun. Her putting make up on me, trying on a wig or a dress. I liked her dressing me up, it was fun and made me feel sexy. She would tell me how beautiful I looked on how, if I wanted, I could get any guy I wanted. She told me she knew a lot of gay guys and would be happy to introduce us. I would try and laugh it off but she knew better, she knew me better than I would let on. I began to love her, not like a man loves a woman, but like how a younger brother would love his older sister. Our talks grew more sexual, and although I still had not admitted my desires to her, she suggested that a “girl” should be ready for her “man.”
Cheryl always had sex toys out in full sight. Shiny pointed tubes and cock shaped dildos, my eyes always drawn to the real looking ones. She said here, picking up a red, realistic looking rubber cock and held it up to my mouth. “Show me how you would suck it” she said, calmly and matter of factory. I said, “I’m not going to do that” even as I sat there wearing lip stick and a pair of her bra and panties. My cock swelled at the idea though, I it was impossible to hide my excitement. “Here” she said, “I’ll show you” and slowly licked around the head of her dildo before wrapping her lips around it and taking it deep into her mouth. “Now your turn” she held it to my lips and I closed my eyes as I let it slide in, clearly turned on. The full feeling in my mouth was amazing, and I instantly knew what was missing from my life.
“Here, let’s try it in your ass” I didn’t even try to stop her or protest. I just let her bend me over and after she lubed up a smaller vibrator, pulled down my panties and rubbed it against my asshole. “You have a nice little hole” she said, “very tight” then slid it inside me, I gasped but my throbbing hard cock told her I loved it. Over time she would start to use bigger and bigger toys and started to jerk me off as she moved them on and out of my ass. She was training me, it seemed, to cum while I was being fucked.
Cherly was very sexual, she always seemed horny. I knew boys were always horny but she was just as bad, and loved to talk about it. It wasn’t more than a few times together when she asked me to go down on her. Thin and shaved, She looked odd to me, just a slit where a cock and balls should be. Though strongly drawn to her, I was not sexually attracted to her, but I would still tend to her needs. Often times I would lick at the top of her vagina on her hard little nub until my tongue was sore and strained. Almost always while I was dressed up and girly.
It wasn’t long until she was taking me out dressed and in make up. Always in a feminine dress or skirt and always with a wig and thick lipstick. Usually to a department store, looking at make up and lingerie, just so girls shopping. Sometimes I would get strange looks, but no one every said anything and I became bolder. “Look at this dress, Jennifer” or “You would look so cute in this thong, Emma.” She would always call me different girly, girl names. Nervous, but I felt amazing, so sexy and free.
The he first time she introduced me to a male friend of hers, I was made up as usual. We were at her place and after a couple beers, he would make comments about how hot I looked. I thought he might even think I was a real girl. When he took my hand and led me to the bedroom I was so afraid he would learn the truth. I should have know Cheryl had set the whole thing up for me.
Behind the closed door of the bedroom, He ran his manly hands all over my body, his touch felt amazing and electrically charged! With his hands on my shoulders, I naturally slid to my knees and began to undo his belt and pants. My heart raced, anticipating seeing my first real cock up close. I was immediately struck by his manly, musky scent, then instinct and desire took over. Licking his shaft and feeling it swell under my lips, I rubbed his cock on my face then licked and sucked softly on his sensitive balls. Returning my mouth to his now rock hard cock, I sucked him.
Loving his moans, encouraged by his grunts, I wanted every inch of him and forced my mouth further down his hard, veiny shaft until I felt him hit the back of my throat, giving me that wondeful gagging feeling. Soon I sensed his orgasm building, his body became tense, his breathing quicken. “Aaaaaaa” was all I heard then felt his warm, salty semen flood into my mouth. The strong taste quickly overwhelmed me, coating my mouth and tongue, making me swallow. I felt so girly, so submissive, so wonderfully used.
When we walked out of the bedroom, Cheryl was right there and asked how it was. “Judging by your huge smile and smeared lipstick, I guess it was better good!” she said to me, I could only smile, shy and girly.
Before too long, I began exploring. Playful, seemingly innocent games with friends, like seeing who’s dick was bigger, or one looks this way what does yours look like. But for me, I knew and felt a deeper urge. I wanted to touch their cocks, I wanted to stroke their cocks. In later years, my lust and desires only became stronger. My desires to pleasure, love and worship cock, so strong, my urges and needs to feel submissive and used overwhelming. Even if I didn’t fully know or understand it. I had a few encounters with other boys, mostly pretending to be clumsy and drunk, afraid to show my true desire to just fall to my knees and make them cum.
It was at my my first job that I met a co worker named Cheryl. Older, Cheryl was nice looking but not beautiful. Thin framed, with long, dark hair, usually in a pony tail and bangs cut straight across her forehead. Almost from the start, she recognized something in me. She would make little comments and questions about if I found a certain boy attractive or if I wanted to see that guys cock. But she was never judging, never condensending. I began to spend a lot of time with Cheryl she was easy to like and easy to talk to.
It started out just for fun. Her putting make up on me, trying on a wig or a dress. I liked her dressing me up, it was fun and made me feel sexy. She would tell me how beautiful I looked on how, if I wanted, I could get any guy I wanted. She told me she knew a lot of gay guys and would be happy to introduce us. I would try and laugh it off but she knew better, she knew me better than I would let on. I began to love her, not like a man loves a woman, but like how a younger brother would love his older sister. Our talks grew more sexual, and although I still had not admitted my desires to her, she suggested that a “girl” should be ready for her “man.”
Cheryl always had sex toys out in full sight. Shiny pointed tubes and cock shaped dildos, my eyes always drawn to the real looking ones. She said here, picking up a red, realistic looking rubber cock and held it up to my mouth. “Show me how you would suck it” she said, calmly and matter of factory. I said, “I’m not going to do that” even as I sat there wearing lip stick and a pair of her bra and panties. My cock swelled at the idea though, I it was impossible to hide my excitement. “Here” she said, “I’ll show you” and slowly licked around the head of her dildo before wrapping her lips around it and taking it deep into her mouth. “Now your turn” she held it to my lips and I closed my eyes as I let it slide in, clearly turned on. The full feeling in my mouth was amazing, and I instantly knew what was missing from my life.
“Here, let’s try it in your ass” I didn’t even try to stop her or protest. I just let her bend me over and after she lubed up a smaller vibrator, pulled down my panties and rubbed it against my asshole. “You have a nice little hole” she said, “very tight” then slid it inside me, I gasped but my throbbing hard cock told her I loved it. Over time she would start to use bigger and bigger toys and started to jerk me off as she moved them on and out of my ass. She was training me, it seemed, to cum while I was being fucked.
Cherly was very sexual, she always seemed horny. I knew boys were always horny but she was just as bad, and loved to talk about it. It wasn’t more than a few times together when she asked me to go down on her. Thin and shaved, She looked odd to me, just a slit where a cock and balls should be. Though strongly drawn to her, I was not sexually attracted to her, but I would still tend to her needs. Often times I would lick at the top of her vagina on her hard little nub until my tongue was sore and strained. Almost always while I was dressed up and girly.
It wasn’t long until she was taking me out dressed and in make up. Always in a feminine dress or skirt and always with a wig and thick lipstick. Usually to a department store, looking at make up and lingerie, just so girls shopping. Sometimes I would get strange looks, but no one every said anything and I became bolder. “Look at this dress, Jennifer” or “You would look so cute in this thong, Emma.” She would always call me different girly, girl names. Nervous, but I felt amazing, so sexy and free.
The he first time she introduced me to a male friend of hers, I was made up as usual. We were at her place and after a couple beers, he would make comments about how hot I looked. I thought he might even think I was a real girl. When he took my hand and led me to the bedroom I was so afraid he would learn the truth. I should have know Cheryl had set the whole thing up for me.
Behind the closed door of the bedroom, He ran his manly hands all over my body, his touch felt amazing and electrically charged! With his hands on my shoulders, I naturally slid to my knees and began to undo his belt and pants. My heart raced, anticipating seeing my first real cock up close. I was immediately struck by his manly, musky scent, then instinct and desire took over. Licking his shaft and feeling it swell under my lips, I rubbed his cock on my face then licked and sucked softly on his sensitive balls. Returning my mouth to his now rock hard cock, I sucked him.
Loving his moans, encouraged by his grunts, I wanted every inch of him and forced my mouth further down his hard, veiny shaft until I felt him hit the back of my throat, giving me that wondeful gagging feeling. Soon I sensed his orgasm building, his body became tense, his breathing quicken. “Aaaaaaa” was all I heard then felt his warm, salty semen flood into my mouth. The strong taste quickly overwhelmed me, coating my mouth and tongue, making me swallow. I felt so girly, so submissive, so wonderfully used.
When we walked out of the bedroom, Cheryl was right there and asked how it was. “Judging by your huge smile and smeared lipstick, I guess it was better good!” she said to me, I could only smile, shy and girly.
Cathalina
- 21.05.2021
- 9
- 0
