Heather s Sissy
- 1 year ago
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The Sissy Trainer Part 1 free porn video
This is my fantasy on being broken in by an older gentleman that is a sissy trainer…
I was finally ready to meet my first real guy. After talking to him for over a week on Squirt, I knew he was the right guy to break me in. Ken was in his mid-50’s, had a nice body over 6 foot. He knew I was new to crossdressing. The agreement was I would follow his instructions and never question him. He told me what to wear before his arrival. Black wig, black & pink high heels, black tube dress that tightly covers my butt and black thigh-high nylons. I was to be fully shaven, not a speck of hair, full make-up, and red nails. He said he picked me because he likes chubby gurls, skinny gurls were not his type. He liked the way we squealed.
Before Ken arrived I checked myself in the mirror; everything was per his orders, I even hiked up my tight dress a bit so it was right under my butt cheeks. The door rang and I answered it. Ken looked me up and down with a smile. In person he was much more rugged than is pictures but his voice was calming. I welcomed him in my home and offered a seat. We sat and talked a while then he just asked me “Are you a virgin?” I told him I practiced with dildos, but nothing real. “Now you remember our agreement correct?” “Yes, I will not question you” Ken went on to say he has broken in many sissies, some took more time than others but he is 100%. Ken looked at the small lump growing under my dress and chuckled “Okay it looks like it time to get start.” He stood up, removed his denim shirt, wow; a nice hairy chest. He told me to gently suck his nipples. I licked and sucked one then the other, “Good gurl.” I continued to lick his chest as he dropped his pants. “I want you to understand and love a real man’s dick” Ken sat on the couch and spread his legs wide. His penis was different in person and it was right in front of me. It moved as he moved and it has a slight bend up like a rhino horn. It was thick and about 8-9 inches long. The mushroom head was beautiful. Ken’s pubic hair was salt and pepper like the hair on his head. It was not as tan as the rest of his body but it was beautiful no the less.
“I want you to lick the tip, then suck the head. Nice and slow to get use to how it feels in your mouth.” Resting my hands on both sides of his thighs, I lowered to my knees and did as told. Licking the tip of his cock, flicking my tongue back and forth, then sucking the head. It felt great in my mouth, the dildos were fine but the real thing was a totally new experience. I sucked his mushroom like it was candy and when I would look up he would give me a smile of acknowledgement that I was doing a good job. “When slowly work your way down the shaft, and watch your teeth” “What is your gurl name?” Stopping for a second, I looked up and said “Lisa.” “Lisa I want you to spit on my cock to get it nice and wet, it will help my cock go down your throat much easier.” I let a nice stream of spit drool on to Ken’s cock and slurped the tip, then worked my way down. My head bobbed as he started to grind my face. I gagged and pulled back to catch my breath; then went down on him again. “Now lay next to me, put your head in my lap and pick your ass in the air.” Ever obedient, I rose up, adjusted my dress to uncover my butt, returned my head to Ken’s lap and went down on him again. Ken for his part leaned back, reached over my back and rubbed my ass. “You like that Lisa?” With his cock in my mouth I sounded yes. His hand felt so soothing rubbing my ass, I was in heaven. I was serving a real man, no more pretending. What was more delightful was Ken started rubbing his finger up and down my ass-crack. I wanted to squirt right then and there!
“It feels like virgin territory back here” I wiggled my butt for him and he slowly eased I finger in my hole. “Okay just lean your head over my lay now and let me know how this feels.” He worked his finger on and out my asshole several times. “Relax Lisa” I did my best, but the excitement of being so turned on and knowing Ken was going to bust my cherry made it difficult.
To be continued…
I was finally ready to meet my first real guy. After talking to him for over a week on Squirt, I knew he was the right guy to break me in. Ken was in his mid-50’s, had a nice body over 6 foot. He knew I was new to crossdressing. The agreement was I would follow his instructions and never question him. He told me what to wear before his arrival. Black wig, black & pink high heels, black tube dress that tightly covers my butt and black thigh-high nylons. I was to be fully shaven, not a speck of hair, full make-up, and red nails. He said he picked me because he likes chubby gurls, skinny gurls were not his type. He liked the way we squealed.
Before Ken arrived I checked myself in the mirror; everything was per his orders, I even hiked up my tight dress a bit so it was right under my butt cheeks. The door rang and I answered it. Ken looked me up and down with a smile. In person he was much more rugged than is pictures but his voice was calming. I welcomed him in my home and offered a seat. We sat and talked a while then he just asked me “Are you a virgin?” I told him I practiced with dildos, but nothing real. “Now you remember our agreement correct?” “Yes, I will not question you” Ken went on to say he has broken in many sissies, some took more time than others but he is 100%. Ken looked at the small lump growing under my dress and chuckled “Okay it looks like it time to get start.” He stood up, removed his denim shirt, wow; a nice hairy chest. He told me to gently suck his nipples. I licked and sucked one then the other, “Good gurl.” I continued to lick his chest as he dropped his pants. “I want you to understand and love a real man’s dick” Ken sat on the couch and spread his legs wide. His penis was different in person and it was right in front of me. It moved as he moved and it has a slight bend up like a rhino horn. It was thick and about 8-9 inches long. The mushroom head was beautiful. Ken’s pubic hair was salt and pepper like the hair on his head. It was not as tan as the rest of his body but it was beautiful no the less.
“I want you to lick the tip, then suck the head. Nice and slow to get use to how it feels in your mouth.” Resting my hands on both sides of his thighs, I lowered to my knees and did as told. Licking the tip of his cock, flicking my tongue back and forth, then sucking the head. It felt great in my mouth, the dildos were fine but the real thing was a totally new experience. I sucked his mushroom like it was candy and when I would look up he would give me a smile of acknowledgement that I was doing a good job. “When slowly work your way down the shaft, and watch your teeth” “What is your gurl name?” Stopping for a second, I looked up and said “Lisa.” “Lisa I want you to spit on my cock to get it nice and wet, it will help my cock go down your throat much easier.” I let a nice stream of spit drool on to Ken’s cock and slurped the tip, then worked my way down. My head bobbed as he started to grind my face. I gagged and pulled back to catch my breath; then went down on him again. “Now lay next to me, put your head in my lap and pick your ass in the air.” Ever obedient, I rose up, adjusted my dress to uncover my butt, returned my head to Ken’s lap and went down on him again. Ken for his part leaned back, reached over my back and rubbed my ass. “You like that Lisa?” With his cock in my mouth I sounded yes. His hand felt so soothing rubbing my ass, I was in heaven. I was serving a real man, no more pretending. What was more delightful was Ken started rubbing his finger up and down my ass-crack. I wanted to squirt right then and there!
“It feels like virgin territory back here” I wiggled my butt for him and he slowly eased I finger in my hole. “Okay just lean your head over my lay now and let me know how this feels.” He worked his finger on and out my asshole several times. “Relax Lisa” I did my best, but the excitement of being so turned on and knowing Ken was going to bust my cherry made it difficult.
To be continued…
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