tagTranssexuals & CrossdressersBirth of a New Sissy Ch. 01

Birth of a New Sissy Ch. 01


Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-)

This story contains male to male sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off!

This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself and locations I knew as a basis. I hope you enjoy it and feel free to send your thoughts, dirty as they no doubt are. It's always good to get feedback!


I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent shape. I wear my hair short with a mustache and goatee. I had been married for about 6 years and had been physically faithful to my wife. I say physically, as I did think about other partners on occasion, though probably no more than most men. What was a little unique was my "dark" sexual secret. Ever since my middle teens I had entertained occasional homosexual thoughts. Nothing really strong or insistent, but enough to inspire some guilty fantasies.

My Bi fantasies were helped along by a one-time encounter with a gay friend in college. It resulted in an exchange of oral sex that seemed to only fuel my Bi thoughts. I still feel I am predominantly attracted to women. I couldn't imagine anything romantic with a guy and my attraction to them was mostly evident when I was horny. Most of the time it was women that would grab my attention.

So here I was without a partner that fateful day, but I had just finished watching the Wimbeldon tennis tournament on TV and as usual had the urge to "smack felt". So it was that I found myself playing against the wall on some courts near our townhouse community. When I got there I was the only one around. So I was startled to hear some polite clapping after I had just finished a make-believe rally against the ever victorious wall.

I turned to regard a well built young man in snug shorts and t-shirt. He was clean shaven with sandy-blond hair. He was built like a quarterback, with a slim well muscled body. He couldn't have been more than 25 years old. There was something familiar about him, but didn't immediately know what.

"Nice rally. I thought you had the wall beat there for a minute." He said with a good natured smile.

"Almost." I agreed, catching my breath.

He walked over and offered his hand. "My name's Jeff, I live across the street from you and your wife."

I reached out and shook hands. He had a dry, firm grip that seemed to hold my hand a second or two longer than I expected leaving me feeling a little awkward. "Mine is Eric. I thought you looked familiar." I said, wiping some sweat with my towel.

"If you're not too tuckered from your match against the wall, we could rally for a bit?"

"Sure," I said. "Why not?"

We hit back and forth for a while and we seemed pretty well matched. He was in better shape and quicker, but I seemed to be a bit more consistent. We ended up playing for another hour or so before we finally stopped. He hardly seemed tired beyond a sheen of sweat. I was done, however.

He came over, hand outstreached. "Good game." He said as we shook again. He put his other hand on my shoulder and gave it a squeeze. " As I released and turned to walk to my bag for a towel I felt his hand slide down my shoulder to the small of my back. It came to rest at the top of my ass. He walked along beside me, his hand almost guiding me as he chatted about the high points of our play. When I reached down to grab my towel I could swear I felt his hand caress my ass as it slid from my waist. I was feeling flustered, even though nothing had really happened. But my heart began pounding and I felt my cock stir.

I just shook it off as me being overly sensitive and not having sex recently. We walked back down the hill towards the townhomes swapping small-talk. I learned he was only recently out of college and was working as a programmer. He worked out of his home most of the week. He was single and currently unattached having separated from his girlfriend after college.

As we approached home he patted me on the shoulder. "Why don't you come in for something to drink. I'm sure we're both dehydrated."

I glanced across the street at my place and considered letting Laura, know where I was, but decided it wasn't a big deal. Jeff noticed my glance and chuckled. "Guess I can see who wears the pants in your household."

I flushed a little. "Just wondering if I should let her know where I was in case something came up." I said a little too defensively. He just chuckled as I followed him inside.

The place seemed fairly spartan. There were a few family looking photos and a computer setup in the family room. He told me to make myself comfortable while he walked over to the computer.

"Need to check my email." After a few seconds he smiled and chuckled about something. "Hey, come over here and look at this." He said pointing to his PC. "I got a friend who likes to send me porn." He looked me in the eye as I came over. "Some of it is pretty hot and some is pretty twisted." He almost seemed to be gauging my reaction.

"I certainly can appreciate good porn." I told him. I looked over and my heart skipped a beat. On the screen was a young college-type stud leaning against a wall, legs spread completely nude. Hanging between his legs was a hard, fat cock of at least 8 inches. I couldn't be sure though since the head of it was lodged in the mouth of a sexy, lingerie clad shemale. She/he was squatting between his legs, arms tied together behind her back while she was impaling herself on a thick, black dildo.

I felt myself flush and my cock hardened instantly at the sight. I'm sure I saw him glance briefly at my crotch out of the corner of my eye. He just said, "not sure which category this one falls into. I got a whole directory full of stuff like this," he continued, pointing at a directory on the desktop called, appropriately enough 'Hardcore'.

I just nodded, not knowing what else to do as he turned and walked to the kitchen to get some water. I found myself looking back at the image, but looked away when I noticed Jeff returning. He handed me a glass.

"I'm feeling real slimy." He gulped the last of the water. "I'm gonna go rinse off real quick. Make yourself at home." Without waiting he turned and headed to the bedroom, pulling off clothes as he went.

I was opening the 'Hardcore' directory as soon as he was out of sight. I was curious what other stuff he had! I was not disappointed. There was a good deal of light bondage and toy action. A disproportionate amount was shemale as well. As I flipped through the images my heart was pounding and my cock was like a rock. It was as if he he had a visual collection of all my deepest, darkest fantasies. I also noticed that in all of them there was a young, smooth stud being serviced in some way by either shemales or women in very submissive roles.

I had skimmed frantically through the entire directory and was going back through it a second time when I realized the shower had stopped! I was in the process of closing windows when I heard him chuckle.

"Hey, don't hurt yourself there!" He stood leaning against the door frame; a towel wrapped around an obviously toned body. "I wouldn't keep 'em if I didn't like 'em. So don't be embarrassed."

He strolled over and stopped just behind me. "Pretty hot, eh?" He said, looking at the last window that I had open. It showed a voluptuous redhead, lovingly nursing on an impressive tool. "It's the look on her face that really says it all, I think." I could feel him leaning over my left shoulder. His voice was low and breathy.

"Look at her full lips stretched around that hard cock." I found myself transfixed by the large photo as he described the scene "There is the sheen of cum and saliva all over her chin which shows that all she cares about is pleasing her man."

I never heard him move, but realized his right hand was resting on my hip. "Why don't you have a seat, it'd be more comfortable than hunching over like that." He nudged my hip with his hand and I found myself sliding down into the chair. He then reached over and zoomed the image full screen.

"The look in her eyes says it all" Jeff's left hand was now on my shoulder and his body was almost leaning against the back of the chair. "It's obvious she is doing what she's always wanted to do." His voice was almost reverent. "Using her body, her mouth like it was meant to be used."

I felt him shift, but kept looking at the picture. My body almost throbbed with each heart beat. My cock was making an obvious tent in my shorts and I didn't really care. "You can tell she was born for this task. Her mouth was created to suck cocks." He continued. "To nurse them to hardness." I could feel my face flush and my mouth dry as I stared at that delicious shaft stretching that lovely mouth. "To pay homage to a strong, virile body."

I felt pressure on my shoulder to turn. "I'm sure you can imagine what she must be feeling, Eric." I let his hand swivel the chair, as he continued. "The curiosity. The need to be submissive to a stronger man?"

I completed the turn in the chair. Jeff stood before me, completely nude. His body smooth, hairless and perfectly toned. Slight washboard stomach. Strong thighs and calves. And there at eye level, hung his cock. Extending from his clean-shaven crotch at least 8inches with a hefty thick shaft. It was the most amazing piece of male equipment I had ever seen.

"You can imagine why she would want to service her master's body, can't you Eric?" He stepped closer. His semi-hard cock only a few inches from my face. I could feel the heat radiating from it. "Finding your true vocation." It filled my vision. "Finally realizing where you belonged in the world." Thick, heavily veined and pulsing with life. His hips moved forward and the head pressed to my lips. "Worshiping the cock of your master."

He pressed forward and without hesitation my mouth opened, allowing his cock inside. My eyes closed and I heard myself let out a low moan as his hard shaft stretched lips. He chuckled at that. "Yes, it feels so good to give in and become the submissive you've always wanted to be." I reached up to his thighs, but he stopped me.

"No!" He said sharply. "You only have permission to touch me with your mouth. Pull down your sweats but leave them around your ankles."

I complied, without letting his cock leave the new home it had in my mouth. In fact at that moment the last thing I wanted was to lose my mouth-lock on his succulent meat. My own dick was almost painfully hard. "Now I see why you were so mesmerized by the cocks in those pictures. Your's is pretty unimpressive, isn't it." It was phrased as a statement, not a question. I had always thought of it as average at about 6 inches. Average or not, compared to his it was unimpressive. "Is Laura really satisfied with it?" He let that hang in the air as his hands grasped my head and began to use slow, deep strokes to fuck my mouth. "Or do you have to use your pretty mouth to make her cum?" I couldn't answer as he thrust deeply info my mouth again.

"You do have a good mouth. I'm going to really enjoy breaking it in." He sighed as his cock began to press into my throat. "So warm and wet. So eager!" He went a little deeper with each thrust. "It's just a waste not to use it. To train it." The air was filled with the wet slurping sounds of my mouth as he slowly worked to breach my gag reflex. I knew what he wanted. I wanted it too. I began to push forward on each thrust. 'Soon,' I thought, 'he will fill my throat.' That sent a shiver through me. Just thinking of this thick meaty shaft violating my virgin throat pulled another moan from me.

"If your little cockette is good enough for Laura, imagine what THIS could do for her hungry cunt!" His hips rocked forward and the head of his cock slipped into my throat for the first time. At the same time my mind was filled by a picture of Laura's voluptuous body on her knees gasping and whimpering as Jeff began feeding his cock inside her. I groaned at the combination of his cock going deeper in my throat and the unfolding scene in my minds eye. There was a whirlwind of emotions inside me. Lust at the images that filled my brain and humiliation at thinking of my wife's pussy fucked into submission under Jeff's pounding shaft. I could almost hear her crying out in ecstasy and begging for more of his wonderful meat.

"That's a good little cocksucker!" He grunted as his balls finally pressed against my chin. I had been so busy wrestling with my emotions that I hadn't realized he was almost fully inserted in my mouth. "I'm fucking your throat now. Warm and tight just like your pretty wife's pussy, I bet." I felt light headed as he would go balls-deep in my mouth and pause for a few seconds before pulling all the way out. "Just like a well fucked cunt. Your wife's well fucked cunt!"He punctuated this with another chocking thrust. "You love this don't you? Being used for my pleasure. Your throat just a willing recepticle for my enjoyment. The joy of submission to my cock." I shivered as I listened to him. It was true. He was fucking my mouth like some cheap sorority slut, and I loved it! I had always had some submissive fantasies, but I never thought I'd be so comfortable servicing a strangers cock.

"Imagine your wife screaming in lust as I stretch her cunt around this thick cock!" I couldn't help it. I was already imagining it. "Of course she'd have to get on her hands and knees and beg me for it." I could see it in my head. Laura on her knees, curvy ass raised high. Two fingers jammed inside her pussy as she begged Jeff to take her. It filled me with humiliation, guilt and raw lust.

My mind was pulled back to the present as Jeff pulled out of my mouth. I let out an involuntary whimper as his saliva and cum coated cock slid from my mouth leaving slimy juices dribbling down my chin and cheeks. Without warning he grabbed my shirt front and pulled me down onto my back. Jeff quickly stradled my head, facing my feet. Without pausing he leaned forward and slid his cock back into my mouth as if slipping back into a wet pussy. He was now truly fucking my face. He held himself up and just used his hips to fuck my mouth with short strokes.

"Suck on my cock with those pussy lips! Milk me good and I'll give you a treat!" He was groaning and I could tell he was close. "That's it! That's it! I knew what kind of person you were when we first met. I could see a weakness there. Someone who needed a strong hand to lead them to where they really wanted to go. To be just a cock sucking sissy!" He pulled out and left his shiny cock just out of reach. "Just think of poor Laura, stuck being poked by a little sissy-boy, when she really dreams of a man's cock filling her with buckets of cum. My cum, smeared all over and dribbling out of her stretched cunt as she shudders from an orgasm like she's never felt before."

I tried to recapture his cock with my mouth but he kept it bobbing just out of reach. "So tell me, how many pairs of panties to you have hidden away?! Tell me the truth, you do have some don't you?"

I tried once more to catch his glistening shaft. I didn't want to answer. I wanted desperately to swallow his cock and lose myself in pleasuring it.

"I asked you a question you little slut!" He barked.

"Yes, I . . . I have some panties."

A chuckle. "How many pairs and what kind?"

"Two pairs of . . . purple french cut panties." I mumbled. "I'm not a sissy or a slut." I protested weakly.

"What would you call a man who willingly gives his mouth and throat for another man's pleasure? Who gets turned on at the thought of his wife being fucked by another man? Hmm? Sounds like a sissy-slut to me." As he said this he rubbed the slippery head of his cock over my cheeks and chin. Never quite letting me get it back in my mouth. "I bet when Laura's out of town you dress in pantyhose, panties and jerk off dreaming of hard cocks, don't you?"

"Sometimes." I said softly. How did he know all this about me? I had always felt that this part of my life was kept closely guarded. I only played occasionally, but I did like the feel of tight pantyhose hugging my thighs, hips and ass. One pair of hose had the crotch cut out so my cock and balls hung free and I could play with my asshole while I masterbated.

"That's a good girl. Accept your destiny." Jeff said and slid his meat back into my mouth. He returned to stroking deep into my throat as he spoke. "That wasn't so hard was it? I'm sure Laura has no idea about your slutty, cocksucking desires, does she? Do you think she'd like to watch you nursing on my cock?" I tried to answer that I didn't want her to know, but couldn't manage more than a hum around his shaft. "She might finally understand why you can't truly satisfy her."

He pulled all the way out then pushed it back between my lips. "Oh, yesss!" He hissed, filling my mouth again. "Work those cunt-lips for me! Show me how much you need my cock in your mouth." He began thrusting with more urgency then suddenly his hips spasmed and he plunged inside me to the hilt. "Oooh you hungry little slut! I'm gonna fill your sissy tummy with hot cum! This is what you've always wanted. Swallow little cum-slut, swallow it all!!" His pelvis was mashed against my face. Balls on my nose.

His hips and thighs trembled as he ground his crotch against my mouth and began pumping warm semen directly into my stomach. After the first couple spurts he abruptly pulled out and began using his hand to drain the rest of his load all over my face. Some landed into my open mouth, but the rest dribbled down my cheeks. I couldn't believe how turned on that made me. I felt so dirty, so used . . . and so horny. I almost wished he could keep cumming. I loved the feel of his stringy spunk splashing across my face.

"Oooh, yeah!" He groaned, still pumping his shaft. "You like it dirty, don't you? Look at your little clitty, so hard and throbbing. You love being covered in a man's cream, don't you?"

I felt myself nod. It was true and my cock (clitty?) was pulsing with each heartbeat. I realized I was rotating my hips like I was a dog in heat. I reached down to stroke it. I needed to cum so bad! But he grabbed my wrists and pulled them over my head.

"No playing with your clitty! I want you just the way you are."

"Oh please let me cum." I whimpered. A part of my mind was appalled at what I was saying. How could I have let myself get into this position. An hour ago I was playing tennis with some guy I've never met. Now I'm on my back in his apartment, pants around my ankles with his fresh cum drying on my face. And I loved it! I was actually kind of glad that he wouldn't let me cum! It meant this warm feeling of lust would continue. I felt so tingly; so alive. I knew at that moment I would do just about anything he asked. His flacid cock was hanging there, still wet from his cum and my mouth. I hoped he'd make me suck it again.

"You will stay right there and not move." He ordered. "Is that clear?"

"Yes." I nodded. Then I flushed as I added, "Sir."

He smiled as he stood over me. "Very good, Erica." I felt an odd rush at the name.

He was gone for a few minutes. When he returned he had some clothing in his hands. He put the small bundle down and pulled out what looked like a single knee-high stocking. He walked over and looped it around my cock and balls, making a soft make-shift cock ring. My sagging shaft got hard immediately as he snugged the stocking down. It seemed to intensify the feelings of lust as it made my cock and balls jut out almost obcenely. I found myself focusing on my clitty-cock as it throbbed within the silky restraint. He produced some scissors and snipped the ends off so there was just a skin colored ring tied around my equipment. It was barely even visible.

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byAltErik© 16 comments/ 244961 views/ 177 favorites

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