Sissy Cheerleader James Gives Blowjobs
- 2 years ago
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Sissy Gives First Blowjob free porn video
I finally decided to take my crossdressing to the next level. I have been dressing for a while now at home, playing with my toys and I felt like it was time to make a move. I made a Squirt ad about meeting a guy for drinks and fun then posted it. After filtering through the responses, I found the man I would service for the first time. He read my response back to him, and said he wanted to meet ASAP. I left the computer to go get myself ready. I did my makeup with blushed cheeks, dark brown eye shadow, pink lips with lip gloss and my nails in a bright girly pink. I had a long black hair piece that fit me perfectly. I put on some sexy satin panties, and a frilly black short skirt with a tight pink spaghetti strap top. I also put on my favorite thigh high pink stockings with a little bow on the tops and my heels that made me feel SO girly.
OMG I felt so naughty, and when I when back to my laptop, I was surprised to see that I had about 7 or 8 more guys asking to meet me! So, this is what it's like to be a girl... lol. One of them really stood out to me. But I had already selected James. He was 6'5” with green eyes and thick black hair, also a short scruffy beard. I really loved his masculine features and I wanted a man that would dwarf me in size so I would really feel feminine.
He seemed like a normal, cool, laid back guy, and was a few years older than me. We agreed to meet at my apartment. The entire time I waited for him to arrive, I was so nervous I had to take a couple of shots. Hearing the buzzer ring, I steadied myself and buzzed him up. After I opened the door slowly, and sure enough, there he was, the hunk of a man was standing in my doorway. I could tell he was giving me the quick once-over and was satisfied. Welcoming him in, he gave me a huge hug and God, did he smell great. We continued to sit on the sofa, have a few drinks and have random small talk for a little while.
"Hey, can you sit a little closer?" he said as he patted the space next to him. As we kept talking, I felt him put his hand on my leg. I was still a bit nervous, but I liked it; and eventually put my hand on his leg as well. We just kept talking casually and softly but subtly caressed each other. I could tell the tension was building and he finally told "You are really cute, you know that right?" If I were lighter-skinned, he would have seen me blush. "I love your outfit, it looks so sexy" he told me, smiling as he grabbed my hand, placed it on his crotch. Before I could react, he pressed his lips against mine. My nerves were racing as we started to make out. I felt so slutty and feminine kissing a man, his scruff felt so hot against my soft make-up covered face.
He ran his hands along my smooth thighs and up and down my tight lacy nylons. At this point we had been making out intensely for 5 or 10 minutes, and I couldn't take it anymore. My little sissy cock was twitching, but my poor little clitty was nothing compared to what was under his pants. Poor little thing lol.
I could only think about pleasing him and getting him off. As we were still making out as I ran my hand up from his crotch to underneath his shirt and caressed his abs. I could tell that turned him on because he started kissing me more forcefully. He grabbed both sides of my head and pulled me in, stuffing his tongue into my mouth. I kept letting out soft girly moans as he did this, and I continued to rub his lower abs underneath his pants, just above his cock. He pulled away briefly and whispered "You're such a bad girl" I gave him the submissive puppy eyes and a nod, before he replied "Just the way I like it" and grabbed my hand, pushing it further down his pants and onto his semi-erect cock. I gave him a smile and lightly started stroking it. His eyes rolled back a little bit and he let out a sexy grunt of approval. "That's better" he said as he moved back in to kiss me. We continued to passionately make out while I stroked him, alternating between gentle and firm strokes. It was so exciting feeling his cock grow in my hands.
After a couple more minutes, I decided it was time. I broke the makeout and slowly kissed up his cheeks and neck until I reached his ear. I gently tongued it and whispered, "you are so fucking sexy", and he let out one of those sexy manly grunts again. I finally pulled my hand off his cock so I could take his shirt off. I straddled him on the couch as I pulled off his shirt and then began to slowly kiss my way down his body, being sure to tongue and suck his nipples a little bit on the way.
My heart was beating so fast as got off his lap and knelt between his legs. I was on my knees in front of him I unbuttoned and removed his pants and pulled off his boxers, watching his cock spring out right in front of my face. I grabbed it again - God I loved watching my painted nails around his thick cock. Moving my lips up to the head and planted a gentle kiss, looking up at him submissively the whole time. I continued to kiss his cock up and down as I stared into his eyes. I wanted to give him a slow, sensual blowjob that he would never forget. I kissed my way down to his balls and then slowly ran my tongue back up to the tip of his cock, and back down. I gently sucked his balls a little bit and then repeated this for several minutes, ensuring to keep eye contact when I could. "God you're such a good little slut" he told me as my tongue ran up his shaft. I nodded and moaned. I finally took his head into my mouth and started to suck. I ran my tongue in full circles around the head in between strokes.
I was finally sucking his cock, I couldn't believe it. I just felt so girly and submissive, I've never experienced a feeling like this in my life. I could feel his cock twitch and pulse in my mouth. It was amazing being able to give someone so much pleasure. I continued to take him in my mouth, working my lips and tongue slowly and sensually around his cock, but deeper each time. I couldn't quite get it all the way in, but I took him as far as I could go and gagged a little as he pressed my head down. He told me he was getting close so I kept working him. I found a good rhythm and started using one of my hands to jerk him as I twisted my mouth up and down his cock. "Ohhhh that's it, don’t stop, don’t stop, suck daddy’s cock" he mumbled and I knew I had him. "It’s okay, you can cum in my mouth baby" I whispered as I increased the pace. I was so excited that James was actually going to cum in my mouth. I continued this pattern and kept making little whimpering noises into his cock as I sucked him off. I think that finally put him over the edge, as he blurted out "Ahhh fuck baby I'm cumming!” as he thrusted his cock further down my throat. With a loud grunt I felt his cock start twitching into my mouth. I moaned as he began to release, jet after hot jet of cum flooded my mouth. I struggled to keep it all in as some of it spilled out of the sides of my mouth and dripped down his cock. I kept lightly stroking and sucking until his cock twitches slowly subsided.
I carefully pulled my mouth off trying not to spill any of his load. As my lips slowly pulled away from his cock, I looked up into his eyes again. I felt like such a submissive whore after what I had just done, sitting there on my knees, between his legs and my mouth filled with his hot cum. He gazed into my eyes for a few moments before smiling and telling me "God you are quite the little cocksucker. Don't you dare swallow yet. Open your mouth." I obeyed and showed him my mouth full of warm sticky cum, trying to get as much as I could of it on my tongue, unfortunately some escaped down my chin. He smiled, clearly proud of what he had done. "Now swallow." I did just that, then caught the bit rolling down my chin, and opened my mouth to prove I swallowed every drop.
"Good girl. Now clean off my cock like a good little slut" he ordered. "Yes, sir" I answered. I slowly and seductively cleaned up all the missed cum with my tongue as his cock slowly started to soften. I gave him a few more playful tongue strokes and sucks to show my submissiveness. He got dressed again and we chilled on the couch and talked for a while. I asked if I he enjoyed himself and if he would ever want to do it again sometime. I was so nervous about my performance, but he said I did a good job.
We cuddled on the couch for a little while more before, then he said he wanted to explore my body more later tonight. “Is that alright?” like I little girl, I just nodded my head yes. I walked him to the door and had to stand on my tippy-toes to kiss him goodbye, and felt so girly as he groped my huge ass. “See you tonight.”
I'm was so happy I decided to take that extra step. Nothing has ever made me feel so feminine, submissive and girly.
OMG I felt so naughty, and when I when back to my laptop, I was surprised to see that I had about 7 or 8 more guys asking to meet me! So, this is what it's like to be a girl... lol. One of them really stood out to me. But I had already selected James. He was 6'5” with green eyes and thick black hair, also a short scruffy beard. I really loved his masculine features and I wanted a man that would dwarf me in size so I would really feel feminine.
He seemed like a normal, cool, laid back guy, and was a few years older than me. We agreed to meet at my apartment. The entire time I waited for him to arrive, I was so nervous I had to take a couple of shots. Hearing the buzzer ring, I steadied myself and buzzed him up. After I opened the door slowly, and sure enough, there he was, the hunk of a man was standing in my doorway. I could tell he was giving me the quick once-over and was satisfied. Welcoming him in, he gave me a huge hug and God, did he smell great. We continued to sit on the sofa, have a few drinks and have random small talk for a little while.
"Hey, can you sit a little closer?" he said as he patted the space next to him. As we kept talking, I felt him put his hand on my leg. I was still a bit nervous, but I liked it; and eventually put my hand on his leg as well. We just kept talking casually and softly but subtly caressed each other. I could tell the tension was building and he finally told "You are really cute, you know that right?" If I were lighter-skinned, he would have seen me blush. "I love your outfit, it looks so sexy" he told me, smiling as he grabbed my hand, placed it on his crotch. Before I could react, he pressed his lips against mine. My nerves were racing as we started to make out. I felt so slutty and feminine kissing a man, his scruff felt so hot against my soft make-up covered face.
He ran his hands along my smooth thighs and up and down my tight lacy nylons. At this point we had been making out intensely for 5 or 10 minutes, and I couldn't take it anymore. My little sissy cock was twitching, but my poor little clitty was nothing compared to what was under his pants. Poor little thing lol.
I could only think about pleasing him and getting him off. As we were still making out as I ran my hand up from his crotch to underneath his shirt and caressed his abs. I could tell that turned him on because he started kissing me more forcefully. He grabbed both sides of my head and pulled me in, stuffing his tongue into my mouth. I kept letting out soft girly moans as he did this, and I continued to rub his lower abs underneath his pants, just above his cock. He pulled away briefly and whispered "You're such a bad girl" I gave him the submissive puppy eyes and a nod, before he replied "Just the way I like it" and grabbed my hand, pushing it further down his pants and onto his semi-erect cock. I gave him a smile and lightly started stroking it. His eyes rolled back a little bit and he let out a sexy grunt of approval. "That's better" he said as he moved back in to kiss me. We continued to passionately make out while I stroked him, alternating between gentle and firm strokes. It was so exciting feeling his cock grow in my hands.
After a couple more minutes, I decided it was time. I broke the makeout and slowly kissed up his cheeks and neck until I reached his ear. I gently tongued it and whispered, "you are so fucking sexy", and he let out one of those sexy manly grunts again. I finally pulled my hand off his cock so I could take his shirt off. I straddled him on the couch as I pulled off his shirt and then began to slowly kiss my way down his body, being sure to tongue and suck his nipples a little bit on the way.
My heart was beating so fast as got off his lap and knelt between his legs. I was on my knees in front of him I unbuttoned and removed his pants and pulled off his boxers, watching his cock spring out right in front of my face. I grabbed it again - God I loved watching my painted nails around his thick cock. Moving my lips up to the head and planted a gentle kiss, looking up at him submissively the whole time. I continued to kiss his cock up and down as I stared into his eyes. I wanted to give him a slow, sensual blowjob that he would never forget. I kissed my way down to his balls and then slowly ran my tongue back up to the tip of his cock, and back down. I gently sucked his balls a little bit and then repeated this for several minutes, ensuring to keep eye contact when I could. "God you're such a good little slut" he told me as my tongue ran up his shaft. I nodded and moaned. I finally took his head into my mouth and started to suck. I ran my tongue in full circles around the head in between strokes.
I was finally sucking his cock, I couldn't believe it. I just felt so girly and submissive, I've never experienced a feeling like this in my life. I could feel his cock twitch and pulse in my mouth. It was amazing being able to give someone so much pleasure. I continued to take him in my mouth, working my lips and tongue slowly and sensually around his cock, but deeper each time. I couldn't quite get it all the way in, but I took him as far as I could go and gagged a little as he pressed my head down. He told me he was getting close so I kept working him. I found a good rhythm and started using one of my hands to jerk him as I twisted my mouth up and down his cock. "Ohhhh that's it, don’t stop, don’t stop, suck daddy’s cock" he mumbled and I knew I had him. "It’s okay, you can cum in my mouth baby" I whispered as I increased the pace. I was so excited that James was actually going to cum in my mouth. I continued this pattern and kept making little whimpering noises into his cock as I sucked him off. I think that finally put him over the edge, as he blurted out "Ahhh fuck baby I'm cumming!” as he thrusted his cock further down my throat. With a loud grunt I felt his cock start twitching into my mouth. I moaned as he began to release, jet after hot jet of cum flooded my mouth. I struggled to keep it all in as some of it spilled out of the sides of my mouth and dripped down his cock. I kept lightly stroking and sucking until his cock twitches slowly subsided.
I carefully pulled my mouth off trying not to spill any of his load. As my lips slowly pulled away from his cock, I looked up into his eyes again. I felt like such a submissive whore after what I had just done, sitting there on my knees, between his legs and my mouth filled with his hot cum. He gazed into my eyes for a few moments before smiling and telling me "God you are quite the little cocksucker. Don't you dare swallow yet. Open your mouth." I obeyed and showed him my mouth full of warm sticky cum, trying to get as much as I could of it on my tongue, unfortunately some escaped down my chin. He smiled, clearly proud of what he had done. "Now swallow." I did just that, then caught the bit rolling down my chin, and opened my mouth to prove I swallowed every drop.
"Good girl. Now clean off my cock like a good little slut" he ordered. "Yes, sir" I answered. I slowly and seductively cleaned up all the missed cum with my tongue as his cock slowly started to soften. I gave him a few more playful tongue strokes and sucks to show my submissiveness. He got dressed again and we chilled on the couch and talked for a while. I asked if I he enjoyed himself and if he would ever want to do it again sometime. I was so nervous about my performance, but he said I did a good job.
We cuddled on the couch for a little while more before, then he said he wanted to explore my body more later tonight. “Is that alright?” like I little girl, I just nodded my head yes. I walked him to the door and had to stand on my tippy-toes to kiss him goodbye, and felt so girly as he groped my huge ass. “See you tonight.”
I'm was so happy I decided to take that extra step. Nothing has ever made me feel so feminine, submissive and girly.
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