My Sissification

Chapter 1

Summer after High school

I was a sexual submissive with my very first girlfriend, Mary Jean.

Mary Jean had an aura of sexuality; sensual and seductive. All her summer clothes were tight and revealing, and I was drawn to her like a moth to flame. We hung out a lot, and sex was all I wanted to talk about. She implied that she wouldn't fuck me, but seemed to enjoy teasing and sex-talk as much as me. She wasn't particularly dominant, she simply responded to my ques. MJ was a knock-out, and used to the cat-calls crude and aggressive boys. I was just as horny, but respectful and safe; probably why we hung so much.

Eventually, I openly begged, if not for actual sex, at least some way for me to come. She was intrigued, seeing me squirm, asking questions, "Why do you need it so bad?" "Take it out; let me see it hard. Let me see you stroke it." So now I am naked, while she has removed no clothing. Still, she is nestled tightly against me. Laying on her bed, I feel her firm breasts pressed to my body, and she's snaked a leg over top of mine, so I can feel her pussy pressing against my thigh. Stroking while she watches, I blast cum all over my stomach and chest - all the way up to my chin, while she squeals in actually seeing something she'd only heard about, watching ropes of cum projecting from a teen aged penis.

Now I want to get dressed, but she insists I lay still while she dabs a finger in my semen, rubs it between her fingers, tastes it, and then brings it to my mouth, "Taste it." I feign resistance, but not enough, and for the first time, I taste my cum . As we softly converse, we take turns, she tastes a dollop, then I am fed a dollop, and we consume most of my load. I could have refused, but I didn't. We discussed the taste and texture, and by the time we were done, it didn't seem so un-natural. For the first time, at a visceral level, I reveled in my willing sexual submissiveness, at the hands of a woman.

She told our mutual friend, Beth, and now I am compromised. They both have power over me; they can tell everyone I was fed my own cum. Part of me wanted to run, but I found myself constantly masturbating, envisioning the two sexiest girls from our school, in varieties of sexual situations, where they teased, and I submitted, and then always rewarded with a mind-blowing orgasm; better than any previous orgasm.

One day we were at Beth's house, they decided we would go swimming in Beth's pool. They changed into tiny, sexy, thong bikinis. I normally wore speedo's, but didn't have them with me. Mary Jean tossed me a woman's bikini bottom, "Wear this." I started to resist, but Mary Jean said, "It's the same size as your Speedos," which we knew wasn't true, but I was game. I tried it on, and as I looked at myself in the mirror, a feeling flushed through me.

The sides were cut narrow and higher on my hips; the rear seemed custom cut to accentuate my butt, and the front barely contained my "junk", cut so close that bits of my pubic hair peeked out the sides. It was way smaller than my speedos, but I loved it, and I wanted the girls to see me like this. I walked out and both girls stopped their conversation, checking me out with quizzical smiles. "From the waist down, he has the best body here," said Beth. And it was true; I was an athlete, with muscular thighs and calves, and a tight, perfectly shaped butt. We all just laughed and frolicked in the pool, and nothing else was said, but Beth was clearly checking me out.

Both of us knew, a sexual door had been opened that would never again be closed. I was profoundly changed. So far, my sexual ambitions were limited to a masculine "fucking" women, but the seed had sprouted, and now a part of me identified with the idea of "being" feminine. I stared at the beautiful bodies of Mary Jean and Beth. I found myself envying their bodies, instead of just wanting to fuck these bodies. I went and bought a new speedo. It was smaller and tighter, with narrower sides. The girls playfully teased me about it, commenting it was smaller than many bikinis.

I spent every chance to be at the pool with Beth and Mary Jean. They laid on loungers on their stomachs and instructed me to untie their bra straps so they could get even tans. Since now they couldn't raise up, they had me "serve" them, setting up fans, refreshing their drinks, and my favorite, put lotion on their backs, which always got me hard, regardless of how I tried to restrain it. They were on loungers, and the optimal way to apply lotion was on my knees, where I had best access to apply the tanning cream, and not so secretly, drool.

They both allowed me spread cream under under the edge their thong bikini bottoms and along their sides. I was tantalizingly close to their beautiful breasts and pussies, and yet they were so completely out of reach. While trying to be subtle, I brought up the topic of sex at every chance, and they teasingly played along. Finally, as Summer was ending, Beth turned over, making no attempt to cover her breasts. I stared, mouth agape, while MJ watched, amused. "Go ahead, do my front. Start at my feet." I was already hard, and there was no way to hide it. Normally I tried to "tuck" my penis straight down to minimize the bump, but this time I freed it, and it grew prominently toward my hips.

As I worked up her legs, to the edge for her bikini, my heart pounded and my sexual tension was palpable, while she was measured and calm. Once up to her stomach, she could reach me, and she nonchalantly stroked a single finger up and down my shaft. As I eased toward her breasts, she had better access, and applied a bit more pressure. My fantasy was coming true. Finally I was caressing her firm, beautiful breasts; white breasts that contrasted starkly against her deeply tanned body; and she was stroking my raging hard on. But her stroking not quite hard enough for me to come. I'm guessing it was her first edging tease, but she seemed to clearly understand what she was doing.

Finally, I said, "Please!" And she said "Please what?" And I said, "Please get me off," no longer caressing her breasts, but kneeling submissively with my hands at my sides. She said, "You do it." So in front of both her and MJ, kneeling between the lounge chairs, I tore down my speedo, gripped myself, and in seconds, a whole summer of sexual tension welled up in my body and burst out in ropes of semen.

I'd never come so hard in my life, not even close. Nothing had prepared me for this life-changing orgasm. I slumped, totally spent, leaving my speedos down, while my penis softened. Mary Jean had also turned over, watching the show. Beth had quietly watched, and finally said, "I think he should shave off that hair," to which they burst into laughter.

I knew I had never really been Mary Jean's boyfriend. I was just a friend, a boy she liked. To Beth, I was more like one of the girls. I was fine being one of the girls. Although I'd been a stellar athlete, I was not one of the "manly" boys, whom they actually were fucking on a regular basis. Actually, I was still a virgin. Whatever my role, I didn't care; every minute we spent together had an air of sexuality.

The phone rang, and I came running, in my tiny speedo, sporting shaved pubes. Upon telling them, Beth said, "Lets see," and I lowered my speedos. She said, "Take them all the way off," which I did, getting instantly hard. She stuck out her hand and I handed my speedos to her, and we all went skinny dipping. Their beautiful pussies were completely shaved; we were all completely shaved, as I also had shaved the sparse hair on my legs, and under my arms.

Soon, they lay on the loungers, all of us naked, me kneeling them between massaging lotion into their bodies. I reveled in massaging their naked bodies, their tan lines, the luscious white breasts tan-lined perfectly by their bikini tops, and the thong tan lines up their behinds, tiny string tan lines around their hips, and the enticing "V" shape molded tan line around the pussies of which I obsessed and yearned.

Mary Jean decided to leave, so Beth and I were alone. She put on a see-thru cover-up, and I was still naked. She said, "I've tossed those speedos. I never liked them. Did you think they were sexy?"

"I guess so. What would you think I should wear?"

"Well, she said, I like most boys in regular trunks, but you are so cute, with those sexy legs and ass. Lets go inside." Soon we were in Beth's room, where she lounged on the bed, lightly stroking her pussy, while I modeled various style panties from her voluminous pantie drawer. It was like we were in a whole new world. I was in Pantie heaven, trying on every style while she watched, placing the ones she liked in a separate pile. "I'll give you some of those, but first come up here and straddle me.

You have such a feminine side, are you gay?" I responded, "I've never thought about sex with boys, only girls." She replied, "You love panties and bras, and although you are super horny, you're not aggressive like most boys. I prefer you to those type boys." She talked about asshole boys, who could be so insensitive and hurtful, that they could take beautiful relationships, and mindlessly shit on them.

Here we were both naked, me straddling her waist, and instead of fucking her brains out, I'm completely soft, having a thoughtful conversation about relationships. "This summer, did you feel used by Mary Jean and me?"

"Yes, and no," I replied. "You were teasing me, but I liked it. I actually liked kneeling while massaging you with lotion; it excited me like nothing else. I was your Servant, but a willing Servant." She casually began stroking me, "So you like being submissive. Would you like to be my submissive?" Rock hard, I could only say, "YES"!

She squeezed my hard penis forward and I groaned as a giant dollop of pre-cum pooled between her breasts, which we both looked at, and without a word, I bent down and licked it up. "I want to hear all your fantasies, but for now, put on the pink panties. Now look at yourself in the mirror." While I surveyed myself in the mirror, she said, "I've read about S&M on line. How about from now on, you address me as Mistress?" "Yes Mistress," I said. "Now, as she spread her legs, I do not want you lick. I want you to lightly kiss my pussy, look me in the eyes, and say, "I AM YOUR SLAVE." Each kiss, I repeated, "I AM YOUR SLAVE", while grinding my pink pantie covered penis against the mattress.

"How often do you jack-off?"

"If it's possible, three or four times a day; but at least once every day," I said, still staring at her gorgeous face, still lightly kissing her beautiful, hairless pussy, softly humping her bed.

"Lets have some fun," she said, and she had me sit at her vanity. First she brushed back my shoulder length hair, then eye liner & shadow, and application of a litany of make-up products, and my face was as gorgeous as Beth's. I stood in front of the full length mirror, wearing only the sexy pink panties, shocked, (and thrilled), that I could look so feminine. Beth took photos, and I posed, the world's newest fem-boy; she added various outfits, a school girl, cheer leader, a mini skirt with high heels, and a spaghetti strap top, and my favorite, Beth's skimpy little thong bikini, the very one she'd teased me in all summer. Even though I had no breasts, I found wearing the bikini top incredibly exciting.

Finally, modeling one of her old (pink) starter bras and matching panties, it didn't seem to matter that I had no breasts; I made a great looking girl, except of course, for the prominent hard-on barely contained by the pink panties. I sashayed in front of the full length mirror while she took photos. I had no fear if the photos wound up on the internet, in this make-up, no one could ever tell it was me. Beth's family once owned a Labor-doodle dog. Beth went and found the old (pink) dog collar, put it on me; the photo session continued. Seeing myself in the mirror, wearing three (forbidden) items, pink panties, bra, and dog collar; chills ran up and down my body. I was transformed to another realm of existence.

Beth had me lay on my back on the bed. Saying nothing, she pulled down the front of my panties, and mounted me. I was no longer a virgin. It felt like I was watching a movie of myself, being fucked by Beth. One would think I'd come in seconds, like a typical teen boy, but I lasted quite a while, savoring every second. I lay still, while Beth slowly eased herself down. Her knees on either side of me, bore most of her weight. She leaned way forward, to where she could kiss me, her hands on my bra-covered breasts, bearing the rest of her weight. In this position, she could lower her delicate pussy onto my penis at a comfortable pace.

First the head, and then she'd stop, and let her pussy adjust. I knew not to thrust. I experienced exquisite torture, remaining still until she eased herself onto me completely. We were perfectly still, and then she gently gyrated. Her eyes were closed, and I simply observed, making no sound or movement. In moments, her gyration became more animated, and soon she was sensually rocking herself on my body. "You're going to make me come," I whispered. And only then did she open her eyes, so she could see my face as I had my first orgasm ever inside a woman.

She stayed on top of me until while I softened, then lay beside me. The panties were biting into me, and I pulled them up, so they'd be more comfortable,

and we soon dozed off. It was dark when we awoke, Beth naked, and me wearing the pink bra, panties, and collar.

She reached and pulled down my panties, and began stroking me. Again she straddled me, eased down onto me. After a few minutes, she crawled up to my face, and I licked. She positioned her clit and whispered instructions, "More tongue", grinding on my lips and tongue, until she orgasmed on my mouth, then she eased, and whispered for me to slow, less and less, and then slid off of me, and again, lay by my side. I asked her to continue, to fuck me, so I could come. She said she was too sensitive, and besides,

"Was I forgetting I was her slave?" I smiled and said, "No Mistress."

Moments later, we were in her shower, soaping each other's bodies, she washed off my make-up, and I was in love. My speedos were gone; so I put on panties to wear under my shorts, and my pockets stuffed with a few more panties, which I'd wear for the rest of that summer, in lieu of my boxers.

Beth and I were together every day for the next few weeks. We'd soon be leaving for separate colleges, and we were compelled to try and squeeze a lifetime of sexual scenarios into a couple of weeks. The next day, she put make-up on my face including bright red lipstick, and the pink bra, panties, and collar. Then she instructed me to tie scarves to the four corners of her bed, with slip knots for my arms and legs, and then put my ankles in the slip knots, then each wrist, and pull them tight. I was wildly excited with the prospect of bondage, a distant sexual fantasy exploding into my reality.

She simply sat on a chair and watched as I bound myself to her bed, with a raging hard-on sculpted by the tight panties. She lay next to me and teased my bra covered nipples, which sent shivers through my entire body, shocked that my (male) nipples could be so sexually sensitive. Then she teased my penis thru the ultra thin panties, and said, "How would you like it if I brought a boy in here and made you suck him off?" My eyes bugged and my mouth went dry. Would she really do this? "Have you ever had a dick in your mouth...tasted cum? Maybe I could straddle you and fuck your cock while he straddles your face fucks your pretty little lipstick mouth." All the while, rubbing my hard-on thru the thin panties; "You're awfully hard. Do you like that idea?" I only groaned, torn between the repulsion of sucking cock, and the ecstasy of her rubbing my cock thru the panties.

Beth grabbed a pair of scissors, and before I knew it, she cut the panties off me. It was indescribably sexy, bound to the bed and powerless as to what was next. She undressed; me marveling at her perfect feminine beauty, and then she mounted me, and eased my cock up inside her. "I'll spare you the cock sucking, but you will be swallowing cum today." Bound as I was, I could move only my hips, which I did in unison, as she rocked forward and back, and in a few moments I exhaled, "I'm coming," experiencing yet another moment of life-changing ecstasy.

As I softened, she smiled down at me, "You will remain bound to this bed until you lick me clean; every drop." Repulsed and freshly fucked, I seriously didn't want to, and the subsequent seconds seemed an eternity as I weighed my options. I'd sort of done this already with Mary Jean and survived. I realized I'd do anything to keep this adventure alive, and coyly said, "I am your slave," which made her smile, and she raised off me and moved up. I saw a white glob of cum at the opening of her pussy, as she lowered her pussy onto my waiting mouth. As I licked, tasting ample cum and pussy, I softly pumped my hips into thin air, relishing my submissive afterglow.

While showering, I watched her shave her legs and pussy, then she shaved my legs and genitals, and nary a stubble remained. She gave me a pantie to wear, and she put on panties herself. Then we sat on the couch and looked over the photos she'd taken the day before. For me, the excitement was palpable, in only panties, like a couple of girl friends, casually sitting on the couch, looking at photos of (feminized) me, wearing a pink dog collar. I told her I loved the photos, and wished to expand and explore both my femininity, and submission.

I told her that I found female bikini tan lines wildly sexy, especially the bikini top tan lines, how they were so exclusively female. I was so excited, my tiny pantie was too small to contain my hard-on. "Take them off," she said, and began laying out various old bikinis. I tried them on, both bottoms and tops. "That's perfect," she said, of a pinkish red one. The bikini bottom perfectly contained my genitals, and the sides quickly narrowed, and at the center of the sides, were girly little string bows. The bra triangles fit snugly over my breasts, with no excess material, and tapered up to strings that tied in the back of my neck. The sides tapered to a strap that hooked in the middle of my back.

Out we went to sunbathe by the pool. I was so excited I couldn't contain myself, and now erect, my hard-on peeked out the side.

Upon seeing, Beth smirked, "That won't do."

"Please," I panted, "If you'll let me come, it'll go back down."

"Ok, she said, but after, you will still do as I say, or I swear, I'll let all my girlfriends see your photos".

"I'll do as you say. I'll be your slave," I said.

She sat in a chair, legs stretched out, and had me kneel and straddle her legs. I eased up until my balls touched her shins. She took out her phone and started a video, clearly showing my face, still wearing the bikini top. She squirted suntan lotion in my hand, and I began stroking. I had never used lotion before, and it felt unbelievable! I looked up at her, mouth agape, knowing I'd come in less than a minute.

She said, "You're going to lick it up after you come," and she eased one foot right under my penis, glided the other along my ass crack, until her toe found my anal opening, and that did it. I blasted my load all over her shin and foot, and continued stroking, slower and slower, until I could take no more. Then, still with our eyes locked, she raised her foot to my mouth, and I started licking. All caught on video.

Now she could use it for blackmail, but instead of being afraid, I was wildly excited. In a couple hours of sunbathing I had a "bra" tan, along with a thong bottom tan. You could wash off make-up, but not a tan. The idea of getting "caught" with a bra tan was constant. Now I had to always be careful, which kept sexy thoughts in the forefront of my mind.