My Sissification

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation.

My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon my body, and it was fading much slower than I'd thought. We were 1000 miles apart, but I still was her "owned" sissy property. Beth's "brand" was burned into my mind as well as my bra tan. Whenever I took off my shirt, the bikini bra outline accentuated my budding sissy-boy breasts, with their unusually large areolas, and way too sensitive nipples.

I wanted to masturbate all the time, but for now, my sexuality had to be a closely guarded secret. I would now have a dorm mate whom I'd never met. Beth used to smile, enjoying her kinky power over me, that compelled me to sunbath in a bikini, both of us knowing, in mere weeks, I'd be at college. I'd have to carefully hide my sissy bikini tan. She'd made me promise, whenever I masturbated, I'd do it on my knees, kissing a pair of her panties. This meant risking getting caught. My roomy could walk in and I likely couldn't hide fast enough; I'd be standing there naked, with a woody, holding a pair of panties. I mused, perhaps the kinkier the sex, the higher the price. I sorely missed my kinky Dom Beth, but for now, I had to regress to the role of a freshman college boy.

Our first day on campus, during Freshman orientation, I found myself waiting in line with a girl who introduced herself as Melissa.

We exchanged pleasantries as we waited in various assignment lines.

She had a lithe 5'-10" body with long, thick brunette hair, and piercing green eyes. We exchanged numbers, and agreed to meet for coffee. I had no intentions of romance, because once again, she'd see my bikini tan, plus I couldn't get my mind off Beth.

Coffee with Melissa lasted for hours; we connected instantly.

Neither of us were interested in Freshman partying puke-fests. We were both socially comfortable, but preferred to keep to ourselves. Melissa's knowledge and ideas were deep, interesting, and insightful. She was mature beyond her 18 years, and yet, if you put her hair in pigtails, she could have passed as an eighth grader. Whether listening or speaking, she looked me in the eye, completely engaged.

I was surprised, and grateful, (and a tad guilty), at how my powerful longing for Beth was quickly displaced by new friendship with Mel. We met almost daily, and quickly we were sharing deep personal intimacies. Sharing about masturbation, I was shocked to hear she'd been enthusiastically masturbating since 12 yrs old, sometimes more than once a day. She'd had way more sex partners than me, (reminder: my total so far, was...1), and she spent hours on line regularly investigating varieties of kinky sex.

"What's your favorite kink?," I asked, and without hesitation she replied,

"Dominance & Submission."

"What is your preference, Dom or Sub?"

"Submission", she replied, and laughingly I replied, "Me too!"

By now, we were longing to have sex, and we playfully joked as to how we'd manage as two Subs.

Mel told me her fantasies were so far, unfulfilled.

She'd offered limited disclosure of her fantasies to her boyfriends. Some were naive, or not trustworthy, so they never even engaged in D & S role playing.

The few boys she did engage clumsily embraced their Dom roles, and the mood was lost before it'd even been found.

Mel's experience was that fantasy fulfillment was easier said than done.

I told her about Beth.

My experience had been the opposite, that reality actually exceeded my fantasies. Upon hearing I had a bikini tan, the sexual dye was cast. We had not yet had sex, but it was only a matter of time. Our conversations began to include intimate details such as, I'd licked up my own come a number of times, I'd had a dildo in my ass, and been out publicly in drag. Mel had once been spanked by a boyfriend while she masturbated. Many times she'd gone to sleep wearing a collar with nipple clamps, and years ago, while dressed in only bras and panties, a best friend tied Mel's hands behind her, and straddled her. Her panties were only inches from Mel's face. She lamented how she wished she had summoned the courage, pursed her lips, and kissed her friend's panty covered pussy. Our sexual energy was palpable; we couldn't wait to delve into our kinky new world.

That weekend Mel's dorm mate would be away, so we'd have her place.

I couldn't believe this was happening; only a few weeks into school, and Mel already knew my closely held secrets, and very soon, Mel would be seeing my bikini tan.

We had agreed I'd be Sub in our virgin sexual foray.

I'd brought to school my bikini, and my favorite pair of Beth's panties; the very panties I'd laid on the bed, kneeled, and worshipped the crotch while masturbating. Still smelling faintly of Beth, I put them on before heading over to Mel's. If she was to see my bikini tan, and I was to be her submissive, I wanted to spice the experience by wearing panties. I'd been yearning to wear these panties, and got hard immediately. Another reason I liked these panties was they were cut just wide enough to contain my hard penis. I was still hard when I entered Mel's room.

"Strip!", were her only words, as she sat down.

First I removed my pants, and she squealed at the sight of my panties. Next went my shirt, and I stood with my hands behind my neck and she took in the sight of a boy in panties, with a bra tan, and a straining hard-on. In seconds she was on her knees pulling down my panties while pushing me toward her bed. I laid on my back and when I looked up, she was already naked and scrambling on top of me. With cat-like movement, she pounced, resting her naked pussy on my penis, hands on my breasts. Just a mere second of grinding on my hard penis, and then she moved up for a kiss. Her tiny body seemed weightless, as she glided over me, then slid up and placed her pussy to my mouth.

I started gently and grew more vigorous upon her ques. Knowing her masturbation history, I knew I'd be licking until she came, and focused completely on her gratification. She'd grunt, and grind into my face, then she'd ease off and I'd slow my tongue motion. The room was silent except for her grunts and sighs. In a few moments, she stiffened, twitched, and then shuttered, coming on my face and into my mouth. She deeply exhaled, then eased away, and laid by my side. Her orgasm had been quick and sweet. I knew there was much more to come.

She nuzzled against me in contented after-glow, but in a few moments, her hand slid down to my penis. I had not shaved since my last day with Beth, and my pubes had not yet grown out. She withdrew her hand with a startle, "You have pube stubble! I'm not fucking a porcupine!", and we both started laughing. Out came the razor, and off came my pubes. It was very erotic and intimate to have Mel shave me;

and it didn't stop at my pubes.

"Yes Mistress," I said, following her instructions, raising each leg, then underarms, and lastly, on my knees, with my ass in the air, both my hands spreading my ass cheeks while she shaved the few stray hairs around my anus. Next I felt a lubed finger stroking my little hole, and soon I was pushing back, beckoning.

"What a slut you are," as her finger slid in deeper and deeper, while I softly whimpered and allowed her tiny finger total control over my entire body. With her finger deeply lodged, she'd move her hand in any direction, and my ass followed.

"Listen to you whimper. You sound just like a girl being fucked by a big cock," which only induced even higher pitched whimpers."

Would you like a nice dildo in your little girl-hole?" And where the dildo came from I never saw, but the head slipped in, and I drew a sharp breath.

"On your back, slut," and as I turned over, she simultaneously worked the dildo deeper. The rubbery texture was fantastic. Even though I'd never felt a real cock, this had to be close. The back end was widened, (for a harness), and rested against the bed, allowing me to move freely against it. Melissa sat between my spread legs watching me rock my hips up and down, back and forth, in and out, and side to side. With smooth and effortless dexterity, her body was upon me. Her hand was guiding my penis into her pussy. "Don't you dare Come," as she worked her pussy onto my shaft. She was incredibly tight! She stopped for a moment, allowing her vagina to adjust to my size, and then eased me in further. This was exquisite torture! I concentrated on NOT COMING! The exquisite torture seemed to go on forever, but finally, I was completely inside her. Her eyes rolled back; she was perfectly still, allowing her body to adjust, which was fine, because just the slightest twitch, and I would have come.

How I wanted to thrust on the dildo in my ass, and blast my cum in her tight little pussy, but I lay still, while she moved almost imperceptibly. Finally I said, "You're going to make me come," and she sensually looked me in the eyes, increased her movement, and I experienced, yet again, the best orgasm of my young life.

Moments later, the sensual dildo inside me, which had induced anal ecstasy, now felt like an anal invader. Melissa seemed to know this, but insisted I keep it fully inside me. It interrupted my after-glow and heightened my sensitivity.

I had previously told her how erotic it had been to be forced lick my cum out of Beth's pussy. Still inside her pussy, my penis had softened, and Melissa eased upon my face and said, "Lick me clean.", the exact words I'd told her Beth had said. As before, I was repulsed, but I was also entranced by being "forced", so my mouth opened, and I licked her beautiful, tight, pussy, as my sweet and salty cum passed over my tongue and down my throat.

I spoke with Beth, telling her about Melissa. Beth told me she and some girlfriends were systematically fucking the entire football team, comparing notes and keeping score. The one rule was they use a condom. She said most of them were just "faceless fucks," with whom she had no further interest. She looked forward to meeting Melissa. The thought of being submissive to both Beth and Melissa sent my head swirling.

Mel and I visited the local adult store. If a man is at the sex shop with a woman, he is automatically validated as alpha to everyone in the place, but not this time. Earlier, she seduced me into my submissive role, but would not let me fuck her, so I was sexually excited. While Mel wore a frumpy sweatshirt and jeans, she had me wearing skin-tight pants and top, and subtle makeup, eyes, face, and lips. With my now shoulder-length hair, I was a "pretty boy". Everyone leered. I was on display; in a sex shop! Gross looking men were undressing me with their eyes, making no attempt at discretion. They had a many varieties of dildos, which Mel and I were drawn to. Mel drifted away, so I was momentarily alone. Unshaven, horny men watched me handling dildos! Again, I was experiencing what many women must feel regularly. One part of me was mortified, and another part of me was holding a dildo that I couldn't wait to fuck.

Mel reappeared holding a plastic "cock lock", making sure all the leering men saw what my fate was to be. We exited with the cock-lock, a long, thick, double headed dildo, a rather intimidating butt plug, a couple different types of dildos, and lastly, a see-thru bra and panty set that was made for sissies. The package had a photo of a femmy male model wearing the bra and panty. His penis bump was just right; not too much, not too little. I hoped I'd look just as good as that sissy model when I wore the set. Moments earlier, I'd been disgusted by nasty, horny men, but I was turned on by the teenaged, hairless model in the photo. I'd fuck that male model in a second.

Back at Mel's, out came the two-headed dildo. We were so horny. Not a word was said. Naked, we laid on our backs, legs spread, butt to butt, and placed each head to our anal openings. We could feel each other's movements, as our sphincters relaxed and the heads eased in. We worked the dildo in deeper and deeper; our unspoken goal was to work it in until our butt cheeks touched. Our heads were propped up with pillows, so we could see the dildo imbedded in each other's ass, and the ecstasy on our faces. Her hand stroked her shaved pussy, from bottom to top, softly massaging around her clit. My hand on my lubed cock; I knew to watch her ques, so we could come at the same time. "Don't you come yet," as she had a mini-orgasm. I backed off, prolonging the experience, letting her set the pace, only slightly moving my ass, not touching my cock. I was entranced, looking at her shaved, sexy, swollen, pussy. Soon her hand was moving with more intensity. I was so enthralled, I was barely touching my cock. And then she came! So loud; anyone nearby would have heard her!

I had not yet come. Now she was super-sensitive, and told me to be perfectly still. Nothing on my body moved except a finger very lightly stroking the underside of my cock, not enough to come. Eventually I spoke, "I liked the male model on the bra and panty package." "I saw you looking at him," she said. You'd suck him, wouldn't you."

"It's the first time I've wanted sex with another man," I said.

She eased off the dildo, leaving it inside me. There was a towel beneath us, and she wrapped it around her end of the dildo, and then propped a pillow against it so I had resistance, and I could grind on the dildo. Next she retrieved her other dildo, and straddled my stomach, placing the dildo to my lips.

"Kiss it," she said, and chills went through my body as I kissed the dildo.

"Now make your mouth into a little "O", and work your tongue in and out. Whenever you suck cock, you will first do this, so your darting tongue will let your partner know you welcome his cock in your little cock-sucking mouth. The man fucking your sissy little mouth will know you intend to give him maximum pleasure."

With her body on me, I could no longer reach my penis, hence, not able to come.

"You like having a nice big cock in your little boy-pussy while you're sucking this cock, don't you? Answer me!", she commanded. "Mmmffff", I groaned as she worked the cock in and out of my mouth, while I wantonly fucked myself in my rear.

Finally she slid back and began easing my penis into her beautiful, tight, pussy. As usual, I had to allow her to ease my cock inside at her pace. "Keep that tongue working," she commanded. She never let up fucking my mouth with the dildo, and I continued working my tongue on the underside of the dildo like a good cock sucker. "You're going to be trained. From now on, whenever your little pee pee gets sexual pleasure, you will have a cock in your mouth. You will be trained to associate your pleasure as a reward for being a good sissy cock-sucker", at which point, while working my tongue feverishly on the dildo, I blew my load into her tight sexy pussy. I was not even finished when she placed her pussy on my mouth and I submissively began licking as she squeezed her pussy and the cum jetted into my mouth. It was only a matter of time before I'd be sucking a real cock, swallowing another man's cum.

Although we both got straight A's, school was uninspiring. We did take an amusing satisfaction in what we considered straight A's in sexuality, in which we studied with commitment and enthusiasm.

For the second semester, Melissa continued school, but I was done. Mel switched her major from Pre-med to Bio-chemical Engineering. I focused on expanding my business, which came with relative ease and obscene profits.

I found us an off-campus luxury apartment on the top of an old warehouse. It offered total privacy and beautiful views.

Despite having some submissive notions, Melissa had completely assumed the Dom role. I embraced my Femmy/Sub identity in totality. My hair was down to my shoulder blades. We put me in various hair-do's, ponytail, pigtails, whatever, and with a little make-up, my face easily was that of an attractive girl. I spent most days in our apartment office, working my business. When at home, I usually dressed only in panties, a bra, a camisole, and heals. In the bra, I wore water-filled, realistic breasts, which I wore 99% of the time. They were removed only when showering, and went back on before I exited the bathroom. When sleeping, the bra and breasts stayed on, and I wore a dainty girly nighty with tiny matching panties. Sometimes Mel picked out what I was to wear. She taught me all about make-up, and I was expected to wear it every day. It was hard not to masturbate during the day, but that was forbidden.

Mel and I had played with the cock-lock, and we both knew I could escape it easily. She showed me a photo of a real anti-masturbation method. It was a ring piercing in the pee-hole, thru the cock head, and another ring piercing in the scrotum. The rings would be soldered, so they were permanent, (unless cut off). Then simply run a lock thru the two rings. The slave's penis head would be pulled down toward the scrotum all the time, until Mistress saw fit to remove the lock. The mere thought of such a torture enforced my resolve to be a very good slave.

I could hear the elevator when Mel was returning home. As became our ritual, I would always be waiting in the entry hall, sitting on my knees, spread open wide, palms up, resting on my thighs. Upon entering, there was no kiss on the cheek. She looked down at me, and approached placing her feet on either side of me, with her (clothed) pussy right at mouth level. While looking into her eyes, I lightly kissed her pussy, and said, "I am your slave." Some days she'd fuck me right there, but most days she would put her slave to task.

On this day, as I kissed her clothes covered pussy, she said, "That's a good girl. I need a massage."

On the spot, I removed her clothes, except for her heels, and panties. She stood with legs apart, and hands on her hips. Again, on my knees, I kissed her panty cover pussy, each kiss, repeating, "I am your slave," my brain-washing mantra, which sent chills every time I said it. Her micro-thin panties were a tiny degree of separation between my lips and her beautiful, sexy, pussy.

We went to the private patio off our bedroom. I laid a large towel on the lounger and retrieved the massage oil. "Start at my feet," was all she said, and I began getting hard at once. This beautiful Goddess had such power over me. As with Beth, I was on my knees for best access. I worked and kneaded each beautiful muscle; up her legs, across her gluts, the small of her back, her shoulders, neck, and then back down. She turned over, and I massaged the front of her body, taking detail with her hands and arms, her forehead, scalp, temples, and neck. I wanted to massage her breasts, but they were off limits for the time being. I had removed her panties, and as I massaged her thighs, I lightly grazed her pussy, but instead of responding as I wished, she simply turned back over.

I was hard, soaking my panties with pre-cum, and wished she'd let me fuck her, but I went through my ministrations. Eventually, I worked on her gluts, and began working the massage oil up and down the crack of her ass, applying sensual touches along and around her tiny little hole. She moaned, queuing me to increase the motions, until I was massaging nothing but her anus. The muscle relaxed and my finger slid a bit deeper. "Tongue," she said, and I kneeled between her legs, held open her cheeks, and probed my tongue. "Deeper," she commanded, and I hardened my tongue and probed deep as I could, over and over.

Finally she turned over and had me sit on the lounger next to her. She had me place one hand under her ass, and keep massaging her anus, and my other hand, she had me stroke up and down her pussy, slightly into her hole, and back up to her clit. She was so orgasmic, in minutes, my fingers moved with her rhythm, and she came hard and loud.