MY SISSYFICATION EVOLUTION ( II )
MY SISSYFICATION EVOLUTION ( II )
Isabella sent the video and all the photos to me. I cherished these photos. For the rest of my life, I'd find myself masturbating, engrossed and cherishing the photos of a newly minted, willing, femmy slave.
The next day found me sitting at her vanity in only the pantie and bra, while Isabella put make-up on me, but very light, barely perceptible. Next were girls shorts that fit nicely, with a colorful belt. Since we'd "bikini-tanned" at the pool, my legs were tanned all the way to my "bikini" line, and in these shorts, looked long and sexy. Next, (over a dainty little bra), was a "metro-sexual" tank top that barely came past the colorful belt. Last, were a pair of flat sandals with thin straps, that adjusted easily to fit my feet. She wore high heeled type sandals making her as tall as me.
Standing together in front of her mirror, we could easily pass as girl friends. The rest of her outfit was tight fitting, and I wished I could have breasts like hers, (and also wished she would fuck me right now!) For the first time, I was going to the world as a girl. There was a biking trail in a town about 30 miles away. We loaded the bikes and headed out. As we drove, I was full of trepidation. "On bikes, men will only get a good glimpse, but you'll be able to see how they look at us."
My fears quickly melted. I loved how they ogled us; how their eyes followed us from the moment we came into sight, until we were out of sight. Some made flirty comments, "Hello girls!" Some seemed sinister, like given a chance, they'd **** us on the spot. None seemed to notice I was a guy. On the way back, we stopped at an ice cream stand and had chili dogs at a pick-nick table, where younger teen boys also ogled us. They were shy, stealing glimpses when they thought we weren't looking. Enlightening as this all was, I was playing a girl, but a very excited boy, and I was dying for sex. We raced back to her place, dove into bed, and for the first time, had sex with me on top. Again, we fell asleep and awakened after dark, and we could hear Isabella's mom downstairs.
Scared of getting caught, Isabella enlightened me. On our first night, when we'd fallen asleep with me in the pink bra, panties, and dog collar, her Mom had opened Isabella's bedroom door, just to check on her, and saw us. I was mortified, but she assured me her mom was ok with everything. So we showered, and went down, and visited with her mom, who was so charming and non-threatening, I was completely disarmed. We discussed college, world affairs, and such, all the while, both of us knowing how she'd seen me.
It turned out to be very liberating. On my way home, I pondered the paradox, the transformation of my abject fear of an adult woman knowing my secret, now relishing the idea that Isabella and her mom could share any and all details about me. What if Isabella and her mom exploited with my sissy slave persona in front of both of them? How far would they go? What if her mom decided she wanted a collage-aged slave boy. Undoubtedly, I'd submit.
That night, I stood naked in front of my mirror, looking at my bikini tan lines. The bikini bottom triangle tan line in front, string tan lines at the sides, and the tramp-stampish little triangle at the top of my butt crack. But the bikini bra tan lines were scandalous! Little girl bikini bra triangles outlined with my nipples perfectly centered. Never had my nipples been anything sexual, and now I stroked them all the time.
I placed a pair of panties on my bed where I could kneel and kiss the crotch, and masturbate. I imagined Isabella sitting on the edge of the bed, legs spread as I kissed the crotch of her panties, saying "I am your sissy slave". Lotion in hand, I stroked, and it occurred to me; Isabella and I mostly "played" sub/dom, but I sensed her 40ish mom could up the ante. Such a taboo! My mind saw her worldly, sexy mom at the edge of my bed as I kissed the crotch of the panties, and blew my load into my free hand, her saying, "Lick," as I tongued my load, swallowing every drop, as I looked into her Femdom eyes.
At 14 years old I'd started a lawn care business, which quickly grew to a million dollar business; with seemingly little effort. I used my football buddies as labor, my mom ran the office; it just came easily to me. I had planned time off for a few weeks before college. But the biz need some attention, so I couldn't see Isabella for a few days. I dared myself, and wore panties every day, a constant titillating reminder that I was now a willing cross-dressing, submissive, sissy. Suddenly I had become a vastly different person; it felt like the world might notice, but I was able to function in my new double-identity.
I had arranged so the Business could operate while I was away at school, with minimal input from me, and still, my income was enough to pay for school and live comfortably. I didn't know what my collegiate future held, but I was ready get away, but first, I was to spend a few more (unbelievable!) days with Isabella.
Isabella had never even untied the bondage scarves from her bed, but merely tucked them out of sight, so I quickly found myself naked and bound at wrists and ankles. Then she added a new bondage twist, and looped belts around my knees, and as she tightened the belts, my knees were drawn toward the sides of the bed.
This was completely immobilizing! I'd never felt so "open" and vulnerable! My eyes bugging, I started to speak and she said, "Shush. Be a good girl, or I'll gag you,"
and then out came not one, but two (matching) dildos. They were molded after real cocks, maybe 8" long, with a texture similar to the real thing. Next she dabbed a finger of lube, and as she touched my defenseless little hole, I jerked and squealed like a girl.
"That's a good girl. Have you been fucked before, or is this your first time? Is this a little virgin pussy?"
She massaged and lightly probed my "boy-pussy", which responded, and I found myself working my hips, silently urging her to go deeper. Then she placed a pillow between my legs and positioned a lubed dildo with the head at my hole, and the rear against the pillow, which provided gentle pressure. Then she simply watched, as my male instincts surrendered, and the dildo eased into my "sissy pussy".
I'd offered no resistance; instead I worked my hips as best I could, trying to get it deeper inside. Isabella obliged and pushed the pillow more, and it was soon 8" deep, and I was a sissy slut in ecstasy, grinding my hips on the cock. The sounds I uttered were not (male) grunts, but girlish high pitched whimpers, working my hips on the cock, up/down, left/right, faster and faster.
My cock was rock hard, with precum just barely easing out. She lightly circled my cock and gave single tantalizing stroke and the precum gushed onto her finger, which she brought to my mouth. I simply opened and welcomed the sweet taste of my precum, sucking on her finger like it was a cock. This was repeated a few times, and I offered no resistance, sucking her finger and rocking my hips like an unabashed slut. Then she straddled me; not to fuck me, up closer to my face, and she brought the other dildo to my mouth.
Now I was sucking a "real" cock, working my tongue on the underside, as if to "pleasure" the dildo in my mouth. The head of my cock barely touched her ass crack, and I worked my hips, trying to increase friction for my own cock, as well as the dildo in my "boy-pussy".
"That's a good girl. That's right; good girl, suck like a good little girl."
And for the first time, with no direct stimulus, my penis blasted ropes of cum, but it was more; my entire body orgasmed. The orgasm originated from deep inside. It was a "full-body" orgasm! Restrained to the bed, I contorted wildly against my bonds, and the orgasm seemed to go on and on.
This was the orgasm of a lifetime, and I'd chase it for the rest of my life.
And then I was limp. She removed the cock from my mouth, but not the one in my rear, and with the pillow still tight between my legs, I could not get it out. I was ultra-sensitive, and Isabella (mercifully) quietly snuggled against me while I recovered. After a few minutes, she touched my nipple, which made me jump. I was not yet ready to be touched, which was erotic torture. Amused, she continued teasing my nipples, so prominent within my bikini bra tan.
"For a boy, your nipples are unusually large, as are your areolas." And they are so hard!" Again, I found myself whimpering; high pitched girly mewing. At that moment, I was all woman/girl, except of course, my "clit" was growing into a 7" hard-on. And then, to make it better, Isabella straddled me, and eased my cock into her soaking, tight, shaved, magnificent pussy. It was the best of both worlds; a nice big cock deep in my ass, and my own cock deep inside her. Having just come, I knew I would last longer, and revel in exquisite servitude, as a nice fuck-toy for Isabella.
I was in heaven. So many discoveries in just a few weeks. From a naive teen boy, my latent sexuality had exploded. I love being submissive, and all things feminine. I loved this 8" dildo/cock in my little "boy pussy". I loved my shaved body. I loved my bikini tan, wearing make-up, and lingerie. I loved having gone in public and easily passed as a girl. I loved that Isabella's mom knew about me, and not only accepted it, but embraced and applauded my sexual courage. I looked up at Isabella. Her eyes were closed, and her face read of pure ecstasy. Her hands on my chest, directly on my breasts, lightly digging her nails in, as she rocked her body on my cock. I loved that we could share this pleasure.
Young and relatively inexperienced, we knew these weeks had been special. This connection, this intimacy, was powerful and unforgettable. Where ever life lead us, we'd be forever connected; we had created an unbreakable bond.
And then, as Isabella began to come, I had another exquisite orgasm.
Isabella sent the video and all the photos to me. I cherished these photos. For the rest of my life, I'd find myself masturbating, engrossed and cherishing the photos of a newly minted, willing, femmy slave.
The next day found me sitting at her vanity in only the pantie and bra, while Isabella put make-up on me, but very light, barely perceptible. Next were girls shorts that fit nicely, with a colorful belt. Since we'd "bikini-tanned" at the pool, my legs were tanned all the way to my "bikini" line, and in these shorts, looked long and sexy. Next, (over a dainty little bra), was a "metro-sexual" tank top that barely came past the colorful belt. Last, were a pair of flat sandals with thin straps, that adjusted easily to fit my feet. She wore high heeled type sandals making her as tall as me.
Standing together in front of her mirror, we could easily pass as girl friends. The rest of her outfit was tight fitting, and I wished I could have breasts like hers, (and also wished she would fuck me right now!) For the first time, I was going to the world as a girl. There was a biking trail in a town about 30 miles away. We loaded the bikes and headed out. As we drove, I was full of trepidation. "On bikes, men will only get a good glimpse, but you'll be able to see how they look at us."
My fears quickly melted. I loved how they ogled us; how their eyes followed us from the moment we came into sight, until we were out of sight. Some made flirty comments, "Hello girls!" Some seemed sinister, like given a chance, they'd **** us on the spot. None seemed to notice I was a guy. On the way back, we stopped at an ice cream stand and had chili dogs at a pick-nick table, where younger teen boys also ogled us. They were shy, stealing glimpses when they thought we weren't looking. Enlightening as this all was, I was playing a girl, but a very excited boy, and I was dying for sex. We raced back to her place, dove into bed, and for the first time, had sex with me on top. Again, we fell asleep and awakened after dark, and we could hear Isabella's mom downstairs.
Scared of getting caught, Isabella enlightened me. On our first night, when we'd fallen asleep with me in the pink bra, panties, and dog collar, her Mom had opened Isabella's bedroom door, just to check on her, and saw us. I was mortified, but she assured me her mom was ok with everything. So we showered, and went down, and visited with her mom, who was so charming and non-threatening, I was completely disarmed. We discussed college, world affairs, and such, all the while, both of us knowing how she'd seen me.
It turned out to be very liberating. On my way home, I pondered the paradox, the transformation of my abject fear of an adult woman knowing my secret, now relishing the idea that Isabella and her mom could share any and all details about me. What if Isabella and her mom exploited with my sissy slave persona in front of both of them? How far would they go? What if her mom decided she wanted a collage-aged slave boy. Undoubtedly, I'd submit.
That night, I stood naked in front of my mirror, looking at my bikini tan lines. The bikini bottom triangle tan line in front, string tan lines at the sides, and the tramp-stampish little triangle at the top of my butt crack. But the bikini bra tan lines were scandalous! Little girl bikini bra triangles outlined with my nipples perfectly centered. Never had my nipples been anything sexual, and now I stroked them all the time.
I placed a pair of panties on my bed where I could kneel and kiss the crotch, and masturbate. I imagined Isabella sitting on the edge of the bed, legs spread as I kissed the crotch of her panties, saying "I am your sissy slave". Lotion in hand, I stroked, and it occurred to me; Isabella and I mostly "played" sub/dom, but I sensed her 40ish mom could up the ante. Such a taboo! My mind saw her worldly, sexy mom at the edge of my bed as I kissed the crotch of the panties, and blew my load into my free hand, her saying, "Lick," as I tongued my load, swallowing every drop, as I looked into her Femdom eyes.
At 14 years old I'd started a lawn care business, which quickly grew to a million dollar business; with seemingly little effort. I used my football buddies as labor, my mom ran the office; it just came easily to me. I had planned time off for a few weeks before college. But the biz need some attention, so I couldn't see Isabella for a few days. I dared myself, and wore panties every day, a constant titillating reminder that I was now a willing cross-dressing, submissive, sissy. Suddenly I had become a vastly different person; it felt like the world might notice, but I was able to function in my new double-identity.
I had arranged so the Business could operate while I was away at school, with minimal input from me, and still, my income was enough to pay for school and live comfortably. I didn't know what my collegiate future held, but I was ready get away, but first, I was to spend a few more (unbelievable!) days with Isabella.
Isabella had never even untied the bondage scarves from her bed, but merely tucked them out of sight, so I quickly found myself naked and bound at wrists and ankles. Then she added a new bondage twist, and looped belts around my knees, and as she tightened the belts, my knees were drawn toward the sides of the bed.
This was completely immobilizing! I'd never felt so "open" and vulnerable! My eyes bugging, I started to speak and she said, "Shush. Be a good girl, or I'll gag you,"
and then out came not one, but two (matching) dildos. They were molded after real cocks, maybe 8" long, with a texture similar to the real thing. Next she dabbed a finger of lube, and as she touched my defenseless little hole, I jerked and squealed like a girl.
"That's a good girl. Have you been fucked before, or is this your first time? Is this a little virgin pussy?"
She massaged and lightly probed my "boy-pussy", which responded, and I found myself working my hips, silently urging her to go deeper. Then she placed a pillow between my legs and positioned a lubed dildo with the head at my hole, and the rear against the pillow, which provided gentle pressure. Then she simply watched, as my male instincts surrendered, and the dildo eased into my "sissy pussy".
I'd offered no resistance; instead I worked my hips as best I could, trying to get it deeper inside. Isabella obliged and pushed the pillow more, and it was soon 8" deep, and I was a sissy slut in ecstasy, grinding my hips on the cock. The sounds I uttered were not (male) grunts, but girlish high pitched whimpers, working my hips on the cock, up/down, left/right, faster and faster.
My cock was rock hard, with precum just barely easing out. She lightly circled my cock and gave single tantalizing stroke and the precum gushed onto her finger, which she brought to my mouth. I simply opened and welcomed the sweet taste of my precum, sucking on her finger like it was a cock. This was repeated a few times, and I offered no resistance, sucking her finger and rocking my hips like an unabashed slut. Then she straddled me; not to fuck me, up closer to my face, and she brought the other dildo to my mouth.
Now I was sucking a "real" cock, working my tongue on the underside, as if to "pleasure" the dildo in my mouth. The head of my cock barely touched her ass crack, and I worked my hips, trying to increase friction for my own cock, as well as the dildo in my "boy-pussy".
"That's a good girl. That's right; good girl, suck like a good little girl."
And for the first time, with no direct stimulus, my penis blasted ropes of cum, but it was more; my entire body orgasmed. The orgasm originated from deep inside. It was a "full-body" orgasm! Restrained to the bed, I contorted wildly against my bonds, and the orgasm seemed to go on and on.
This was the orgasm of a lifetime, and I'd chase it for the rest of my life.
And then I was limp. She removed the cock from my mouth, but not the one in my rear, and with the pillow still tight between my legs, I could not get it out. I was ultra-sensitive, and Isabella (mercifully) quietly snuggled against me while I recovered. After a few minutes, she touched my nipple, which made me jump. I was not yet ready to be touched, which was erotic torture. Amused, she continued teasing my nipples, so prominent within my bikini bra tan.
"For a boy, your nipples are unusually large, as are your areolas." And they are so hard!" Again, I found myself whimpering; high pitched girly mewing. At that moment, I was all woman/girl, except of course, my "clit" was growing into a 7" hard-on. And then, to make it better, Isabella straddled me, and eased my cock into her soaking, tight, shaved, magnificent pussy. It was the best of both worlds; a nice big cock deep in my ass, and my own cock deep inside her. Having just come, I knew I would last longer, and revel in exquisite servitude, as a nice fuck-toy for Isabella.
I was in heaven. So many discoveries in just a few weeks. From a naive teen boy, my latent sexuality had exploded. I love being submissive, and all things feminine. I loved this 8" dildo/cock in my little "boy pussy". I loved my shaved body. I loved my bikini tan, wearing make-up, and lingerie. I loved having gone in public and easily passed as a girl. I loved that Isabella's mom knew about me, and not only accepted it, but embraced and applauded my sexual courage. I looked up at Isabella. Her eyes were closed, and her face read of pure ecstasy. Her hands on my chest, directly on my breasts, lightly digging her nails in, as she rocked her body on my cock. I loved that we could share this pleasure.
Young and relatively inexperienced, we knew these weeks had been special. This connection, this intimacy, was powerful and unforgettable. Where ever life lead us, we'd be forever connected; we had created an unbreakable bond.
And then, as Isabella began to come, I had another exquisite orgasm.
1 year ago
