I have always known that I had different urges than other males my age. When I was a teen, my best orgasms always came when I was wearing my sister's silky panties, bra, and nylons, and ramming whatever object I could find up my horny ass. I was especially excited by the transexuals in the tabloid magazines, and often fantasized about what it would be like to have sex with one.
Here it is, now many years later, happily married and a decent enough sex life. Some of my most powerful orgasms are still "solo" though, and happen while I'm dressed in black silky control top pantyhose, with a buttplug buried in my ass and a dildo in my mouth. My favorite position is kneeling in front of our computer, while looking at images of a shemale being sucked, and then ass-fucking a kneeling submissive male. I imagine myself submitting to my TS's desires, and being thoroughly fucked by her. A few minutes of good dildo sucking and ass-reaming and I'm blowing a big load in my hand. Sometimes I also imagine I'm the very womanly TS, having my way with a formerly straight male, blowing my load up his tight, willing ass.
Which brings me back to the present. I have frequent fantasies about a chance encounter with a TS while on an out of town trip. It usually goes something like this...
It's been awhile, but here I am back in Oklahoma City on an extended business trip. Had to fly in on a Friday, but don't have anything going on until Monday morning. I check into the Residence Inn, and unpack my things for my stay. As usual I've packed some of my special clothes and my "toys" to help relieve the "tension" while I'm on the road. I did some afternoon shopping to stock up the fridge and relaxed in the apartment until dinner. After a nice steak at the Outback I decided to head out for a few drinks and shoot some pool. Went back and took a quick shower to get the road grime off, and decided to be daring tonight and wear some of my accessories for my evening out.
I got out a pair of nude, crotchless pantyhose and slid them up my legs slowly, savoring the feel of the silkiness against my legs. I then took out my buttplug and greased it up thoroughly and slowly teased it past my tight sphincter. I didn't seat it right away, but slowly worked it in and out of my hole, getting used to the sensation. When I was thoroughly loosened up, I pushed it in the last couple of inches and it popped in, seating 5" of rubber cock in my ass. I squirmed around, making the plug move around and stimulate all the right places. I then pulled out my favorite pair of black silky panties and eased them up my legs, and tucked my hardening cock into the glorious fabric. I then strutted around the apartment and checked out my reflection in the mirror, excited at the prospect of going out in my hidden finery. I finished dressing in some comfortable Levi's and a sport shirt, with socks and shoes to hide my nylon clad feet. I then set out for an evening of fun.
During the drive I continually adjusted myself in the driver's seat, stirring around the plug around in my horny ass. I was already thinking about how good it would feel when I got back to the apartment and would jack off a big load. I had already decided to get out my 9" dildo and give myself a good reaming when I got back. For now though, I picked a small local bar, which I knew to be fairly dark and intimate for my evening's drinking. I checked the buttplug one last time before heading in, then took a set at a remote corner of the bar where I could watch everyone.
I had three bourbon and cokes before I got up the nerve to put 50 cents onto the pool table. It was a slow night due to a Sooners home game, so my game came up quickly. I wasn't paying attention to the table, and was startled when a good looking woman came up to me asked me if I wanted to play. I quickly regained my composure and followed her to the pool table. While I was racking the balls I had a chance to look her over a little more closely, and was impressed with what I saw. She had to be mid thirties, about 5' 8", shoulder length auburn hair, and the prettiest green eyes I had ever seen. She had nicely shaped boobs that peeked out of her low-cut top, a very sexy ass, and a body that was very trim and well proportioned. Her deep tan and gold jewelry completed the package. I was already forming a mental image of stripping her down to her own panties and hose, and rubbing my body against hers. I had to readjust my cock before I straightened up, as it was straining against the silky fabric.
I introduced myself to my opponent and she told me her name was Shawna. I was surprised when she asked if I wanted to play for anything. Being a fairly competent pool shooter, I agreed to play for a drink. Shawna broke the rack well, sending the balls scattering over the table. The game was close, but I ended up sinking the eight ball after she missed. She ordered us both another drink while I waited for the next player to challenge the table. Shawna and I talked for a couple of minutes, during which I found she was currently unattached. When no one else showed up to challenge the table, Shawna asked if I'd like to play another one. We again played a close one, with Shawna running her last two balls and then the eight. I bought her a margarita and another bourbon and coke for myself.
We sat and drank and talked for awhile until suddenly she jumps up and grabs my hand and leads me to the small dance floor, "this is my favorite song" she squeals. We dance slowly, not too close at first, then gradually our hands start to roam over each others' bodies, and our tongues explore each others' mouth. In a moment of panic I feel Shawn's fingers probe my asscheeks and nudge against the probe buried between them. I start to push away from her but she holds me tight and says "don't worry baby, I really enjoy having my butt filled sometimes, it's not a problem with me". I look at her closely and decide "what the hell", she already knows and it doesn't bother her. So I relax back into her arms and we continue fondling each other as we dance. She definitely enjoys wiggling the probe around in my butt causing my dick to swell in its silken prison. We finish our dance and head back to the bar, holding hands as we walk.
Shawna orders us both a shooter of Cuervo Gold and we both down them quickly. By now I'm pretty hammered, and really into kissing and fondling Shawna's body. She looks at me coyly and asks if I'd like to play one more game of pool for different stakes. I am definitely interested and ask her what the terms are. "If you win, I'll give you the best blowjob of your life, and if I win, you have to let me ream you out good". I couldn't see a losing side to this proposition so I quickly agreed to her terms. This game turned out to be no contest. I let Shawna break and watched as she ran the table out on me. I smiled at the implications of my loss, thinking how much of a turn on it would be to have Shawna playing with my ass.
As we sat back down she handed me two little blue pills and took two herself. "What are these" I asked suspiciously, and was surprised when she replied "Viagra, great for an all night hardon and it even helps the female libido". I immediately popped them in my mouth and took a chug from my drink. I was amazed at my good fortune this evening, and could only imagine the awesome sex that was waiting for us.
As the Viagra started taking effect I started noticing blue halos around the bar lights. I asked Shawna about this and she told me it was a good way to tell that the drug was taking effect. That and the rock hard boner she was stroking through my jeans and panties. We finished our drinks and headed for the door, with Shawna playing with the buttplug as we walked. "We'll go back to your place if that's okay with you" she asked, which I quickly agreed to. She followed me back in her car and we quickly made it up to my apartment.
"Remember our bet" she said with a smile and asked me to strip for her. I hesitated briefly but then thought "what the hell, she already knows and is cool with it" so I kicked off my shoes, peeled off my socks, and pulled off my jeans and shirt. I stood in front of her and blushed and she told me "you have such a nice butt, I can see why it really turns you on to have something in it". With that she drew me to her and we kissed very passionately while she worked the rubber cock around in my ass and caressed my steely rod. I was so turned on I almost came on the spot. "I usually like to use a dildo on my ass when I'm really horny" she smiled, "you wouldn't happen to have one of those handy would you?" she asked. My immediate blush gave her all of the answer she needed. I reached into the bottom of my drawer and pulled out the stiff 9" dildo and showed it to her.
"I have one just like it at home" she laughed, putting me at ease.
Shawna took the dildo from my hand and slowly worked it around in her mouth, until she was ultimately taking the whole thing down her throat. She removed it sensuously, licking it repeatedly before placing the tip against my lips. "Show me how you suck on it" she said, "I know you've done it before". I eased my mouth onto it and started bobbing up and down on it, trying to imitate what Shawna had done. She started ramming the dildo into my mouth while working the buttplug furiously around in my ass. I had never been as hard or turned on before in my life as with Shawna. I was humping back against the plug and plunging my head as far as I could onto the dildo.
I was delirious with pleasure and very close to cumming. Shawna slowed things down and told me I had earned the best blowjob in the world even though I had lost the pool game.
Shawn told me to take off my panties, which I immediately did, and was surprised, when she popped out the buttplug and pushed me back on to the bed. "You need something bigger in there" she smiled and pushed my legs up and slowly started working the big dildo into my already stretched ass. I pulled my legs back toward my chest to give her better access to my chute, and she definitely knew what to do. She purposefully slid the whole length in, twisting and making me writhe with pleasure. Once she had it seated firmly she took hold of my rigid cock and started working her magic on it. Her tongue danced over the head of my cock, which was already straining from the Viagra and her extremely pleasurable action in my rear. Her mouth slowly descended the length of my shaft, while her tongue massaged the sensitive underside. She began to pump the dildo in and out of my ass very deliberately, while bobbing her head up and down, taking my whole length down her throat.
The pleasure I felt was indescribable. Shawna had me so turned on I knew it was going to be the best orgasm of my life. Sensing my impending climax, she started jacking me real hard, while ramming the dildo in as far as it would go. "Give it to me baby" she commanded and I responded immediately. The cum seemed to start in the depths of my ass, coursing up through my straining cock, and exploded into her warm waiting mouth. I was moaning loudly as the jism boiled out of my body, gush after gush of love juice, all greedily lapped up by Shawna.
She smiled at the intensity of my experience, and moved her body alongside me on the bed. She placed her hands on either side of my head and locked me in a passionate kiss. I realized with a start that she had kept most of my huge load in her mouth, and was now forcing it into mine. I struggled briefly, but she maintained her grip and continued passing my slimy ooze onto my now curious tongue. I had tasted a little of my own come before, but this time I was being forced to take a whole load. The taste was somewhat salty, with a slightly bitter aftertaste. Not gourmet fare, but definitely not the worst thing I had ever tasted. When she had emptied the contents of her mouth into mine, she drew back and stared into my eyes "was it everything I promised?" she asked with a grin. ""That is the most intense orgasm I have ever had in my life" I exclaimed, still trying to catch my breath from the very pleasurable workout. "Remember our bet though" she replied impishly, "now you have to do what I want!" My cock spasmed at the thought of what else she had planned for me.
Shawna stood up from the bed and slowly started to undress, first removing her top, and revealing very nice breasts, barely contained by a black see-through bra. She then slid her form fitting jeans down, revealing a pair of black slimming panties, much like a pair I had. "First I want you to worship my breasts" she revealed, and unhooked her bra and let it drop to the floor. I sat up on the edge of the bed, and she immediately thrust her horny nipples at my face. My tongue traced circles around each nipple, teasing each to rock hard firmness. I massaged and kneaded each breast, causing Shawna to moan with delight. I was pleased to know she was really getting off on my tonguing. "You need to move that mouth lower" Shawna moaned lustily", and reached down to slip off her panties and show me my treat.
As I moved in towards her mound I was startled by the sudden appearance of a very swollen and purple cock staring me in the face. "You don't know how good it feels to finally let it free" Shawna said suddenly and grabbed my head before I could react. She rammed her cock into my startled face and pushed me back on the bed, straddling my chest and forcing her cock deeper into my mouth. I struggled to repel the invader but her grip was strong, and her thighs had my arms pinned to the bed. "Come on baby, you know you really wanted this" Shawna said teasingly as she worked her very large cock in and out of my mouth. "If you do a good job I'll even let you taste my come" she said with a laugh as she pounded away at my face.
Having overcome my initial shock, and somewhat inebriated state, my mind struggled to comprehend what was happening to me. I obviously had a very large cock pumping in and out of my mouth, and it was attached to what was otherwise a very beautiful woman. My mind struggled with how to deal with this situation, but it was my "other" head that ultimately made the decision for us. My somewhat deflating cock had sprung to life and was throbbing almost painfully while my face was being fucked. This same fact had not escaped Shawna, and she reached down and grabbed hold of my steely rod. "That's it baby, get with the program, you know you've wanted this for a long time", she observed quite correctly. With the matter finally settled, I decided to make the best of an unusual situation.
I had practiced giving head to my dildo many times but this was my first attempt on the real thing. I tightened my mouth into a ring around her cock and moved my tongue around the glans underneath, stimulating her in the same way she had just brought me such pleasure. Shawna eased up off the bed allowing me to slide my arms out and wrap them around her waist, pulling her hips and cock closer to my face. She immediately responded to my change in attitude by stroking my cock harder, increasing the urgency of my sucking.
"Here baby, work this into my ass" Shawna said, handing me the big dildo that until recently had been buried in my own chute. She must have greased her ass up earlier, because the dildo slipped in without resistance, until almost the full length was buried in her. "OOOOOH YEAH!!" Shawna moaned as she increased the vigor of her mouth fucking, causing my throat to stretch and accept the very head of her cock. "Oh fuck that feels good!" Shawna exclaimed as I hoped I was giving as good a blowjob as I had received only a short time ago.
I worked the dildo around mercilessly in her ass, making her squirm and pump my face with wild abandon. "Get ready baby" she moaned, "you're about to receive your reward for being such a good cocksucker". With that encouragement, I plunged the dildo as deep as I could, and suctioned her cock as deep as I could down my throat. A deep guttural moan escaped her lips as I felt her swell menacingly in my mouth and the first shot of a very large load gushed into my waiting mouth. Shawna pounded my face brutally as she pumped what seemed like gallons of come into my already full mouth. Each successive spurt bubbled out down my chin and onto my chest where it pooled in globs. I gasped at the volume of come I was swallowing, and the amount that I just could not gulp down.
Shawna fucked my face for what seemed like hours, as her body drained it's love juice into my face and down onto my chest. Shawna gave one final gasp and collapsed down onto my body, with her cock slipping out with an audible pop as her come drooled out of my thoroughly fucked mouth. "Oh yeah baby!" she sighed, "it's been a long time since I had a blowjob that good, you may have just earned the right to experience a good ass-fucking tonight". I squirmed under her, anticipating what I knew would be a very new and exciting experience for me.
Shawna made me clean up all of the come smeared all over our bodies, either by licking it off of her, or scooping it up with her fingers and feeding it to my lips. "That's it baby, get us all nice and clean so we can have even more fun!" she playfully said as I finished cleaning up the last of her voluminous load. Shawna slid the dildo out of her ass and grinned at me "we better get you loosened back up for your initiation" she smiled, as I noted her own cock favorably compared with the dimensions of my favorite toy.
The Viagra was continuing its effect, as both of us were rock hard, even after our intense orgasms. My cock twitched as Shawna worked the dildo in and out of my already greasy hole, while her other hand stroked slowly up and down my manhood. The feeling was utterly incredible, especially with the knowledge that her "womanhood" would be replacing the imitation cock now filling my ass. "Ooh, you're good and loose now" Shawna cooed, "I'll bet you can't wait for me to fuck your virgin ass". She had me nailed both figuratively and for real.
I reached up and began stroking her throbbing cock, knowing it would soon fill the need in my horny ass. "That's it baby, get it good and hard for your ass" she encouraged, as she continued plunging the dildo deeply into me. "I want you on your knees when I shoot my load into you" she explained, "but first I want you on your back so I can watch your face when I pop your cherry" she ordered. She suddenly popped the dildo out of me, threw it on the bed, and positioned her body between my thighs, with her cock pointing menacingly at my gaping hole. "Get ready baby, here it comes" she cooed as she eased herself into my comfortably stretched ass. There wasn't any pain as the head popped past my sphincter, the good reaming I had already received made sure of that. Then her length thoroughly filled me as she seated her cock deeply in my gut.
Shawna stared intently at me, her eyes peering deeply into my soul. "I wish you could see yourself right now" she said seriously, "the look on your face is one of pure joy". It was then I knew what I had been missing all of those years, denying what was truly a part of me, hiding it away and ignoring it's existence. With that realization, I began to really enjoy what I was experiencing, grinding my ass back against Shawna's cock, driving it as deep as possible into me. Shawna grunted pleasurably as my ass gripped her cock and squeezed it as she pumped it in and out of me. "Put your legs up over my shoulders" Shawna moaned as she continued pounding deep into me. Rolling my hips back seemed to open me up even more as her cock explored ever deeper into me. She crushed her body down on mine, mashing her tits into my chest and dove her tongue deep into my mouth.
The feeling was almost overwhelming, my cock was iron hard, rubbing between our sweaty bodies as she continued my initiation into womanhood. My hands were all over her body, twisting her nipples, squeezing her ass cheeks, and pulling her deeply into me. Shawna humped me like this for close to a half-hour, easing off each time she got close to cumming. "It's about time you experienced your first load up your ass" Shawna commanded, "get on your knees so I can really fuck you!". With that she popped her dick out, and I quickly rolled over to comply and allow her to fill my emptiness.
I was now kneeling face down on my bed, my ass filled to the brim with her cock, when she wiped off the dildo on the sheets and handed it to me. "It'll feel even better if both holes are filled" she urged as she continued filling my ass with her hot cock. The dildo tasted funky, but I eagerly sucked it in, imitating the technique I had used earlier to coax a huge load from her. My other hand sneaked down to my own throbbing cock and began stroking it quickly. "That's it baby , suck it!" Shawna urged as her pounding increased in intensity. Each thrust of her hips drove me down on the imitation manhood, making me feel as if I was being fucked by two cocks at once. Shawna was rapidly approaching orgasm as I felt her cock grow to ever larger dimensions. "Stroke your little clitty" Shawna urged as I pounded my own cock as hard as I could in time to her plunging deep into my ass.
Shawna had me to the edge of reality, I was no longer in control of myself, it was not my voice telling her "fuck my ass mistress, fill me with your cock, come in my ass!" Not that she needed any encouragement, but it had the desired effect. She was slamming me hard with each thrust, driving her cock deeper than I could believe possible. . With a strained groan, Shawna began pumping her hot seed deep into me. The first hot blast triggered a response from my overstimulated prostate, and my come boiled out with such heat and force I thought I would surely pass out. Each shot from Shawna brought forth a new surge from my own cock, as if her come was passing directly through me.
We both climaxed continuously for what seemed like several minutes, as my ass milked every last drop from her, and my hand coaxed every last drop of come from my body. We both must have actually passed out, as the next thing I remember is waking up flat on the bed, Shawna sprawled across my back, and her still firm cock planted solidly in my ass. It was a good thing as I could feel the huge load of jism filling me and dribbling down my ass cheeks. Shawna moaned into my back and spoke between deep breaths "that was one of the most intense orgasms of my life" she wheezed still out of breath.
I could only groan in agreement, as my own breath was coming in gasps.
Once we had both recovered sufficiently, Shawna rolled over and smiled mischievously at me, "I'm not finished with you yet baby" as she reached for my painfully erect cock. "I need a good fucking tonight too, and you have the right tool for the job." With that she rolled me onto my back and positioned herself over me. She squatted slowly, easing my cock into her ass inch by inch until she was fully impaled on me. Next she picked up the lonely dildo, and plugged the gushing torrent from my hole. She then began a slow up and down motion, while fondling her breasts very sensuously. My hand found her cock and began stroking up and down, squeezing her balls, and pinching her piss slit, making her increase her tempo on my cock. She responded by working the dildo ever deeper into my thoroughly stretched ass.
It was truly an incredible sight, her incredible femininity bouncing up and down on me, her fingers roaming her nipples, and her 8" cock pointed directly at my face. "Cmon baby hit my mouth" I playfully teased as she groaned and squeezed my cock tightly in her chute. I could only groan in reply as my load worked it's way from deep inside me. We were deeply in tune as her cock began to pulsate menacingly, my own cock getting ready to deposit it's own load. It was as if we both climaxed as one, our cocks spurting hot juice together, with mine spurting into her guts, and hers not surprisingly landing on my outstretched tongue. "Give me all of your come baby, right on my face" I urged her, as my own boiled up out of my body and filled her to overflowing. My come was running down her thighs and onto the bed, while hers landed on my hair, face, tongue, and chest. I could not believe the amount of come she was able to produce, even after her very large load earlier. I greedily licked up all I could find, and milked the remainder out of her, causing her to moan and shudder.
Shawna sprawled across me, our tongues intertwined as we enjoyed the afterglow of our experience. While the Viagra had worked for quite awhile, its effect was beginning to finally diminish, allowing my cock to soften up.
With a pop it pulled free from her and immediately my warm come began gushing out of her gaping ass. I caught as much as I could and rubbed it all over her ass, making it sticky with my juice. Shawna laughed playfully and told me "you know you're going to have clean that up don't you?" I smiled and told her "with pleasure ma'am".
We laid in bed and talked for awhile, and Shawna told me of her transformation, and her problems with finding open-minded men in Oklahoma. "My last boyfriend didn't mind fucking me" she explained, but would never suck her cock or allow himself to be fucked. I held my breath for what I hoped was next, "would you be my boyfriend?" Shawna asked tentatively, making my heart leap with joy. "I don't know what it is, but I feel so wonderful with you". I could only reply in kind, "Shawna, you have opened a whole new world to me, and I sure don't intend to turn my back on it now!" I replied, finally accepting what I knew to be true my whole life. "I'd be proud to have you as my girlfriend and make all of the other guys jealous!". Shawna and I embraced passionately, tears streaking down our faces as we held each other for a long time. "Why don't you pack your things?" Shawna told me, "I have a very large house with plenty of room. "And don't forget your special clothes and your toys" she added coyly. I could see that I was in for the experience of my life, and I knew I was finally ready for it...