Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for a drink; for whatever reason, he’d chosen not to show.
His mistake was my gain. I felt her hard nipples pressing against me through the satin top she wore and she felt something equally stiff poking her ribcage; I wondered if she’d been checking me out as much as I’d been drooling over the shape of her bubbled butt and not long after we were heading to her car. Words were few on the way to her apartment, as we both knew what we wanted; the two of us finding heaven atop her queen bed shortly after arriving there.
As she rode my cock by way of a reverse cow-girl style, her jugs jiggling to and froe, I know she believed it was her that kept me hard for a full three rounds, but I couldn’t tell her the truth. It was the wicked thoughts of utter depravity about my friend Jason that I held within my cranium, which kept the lead in my pencil as we climbed towards orgasm number four. I reached forward to fondle her delightfully firm cheeks as my prick vanished and reappeared intermittently; she groaned as I explored her sphincter.
Before the next sun rose, I awoke to Kym sucking my limp snake until it stiffened nicely into the python from the previous session; then she lead me to the bathroom, the hot water cascading over our bodies as we fucked once again. In between the gentle thrusts, we spoke a little but said a lot; exchanging important information that confirmed we were each childless, unattached and looking for someone who could rock our worlds.
The unmistakable glint of hope reflected in her eyes and I couldn’t help but wonder if she was recognizing it in mine as the water swirled about the drain at our feet. It was confirmation of the thoughts that we shared, feelings that fate had brought us together for a reason greater that just physical satisfaction.
With her hair dripping onto the towel that was wrapped about her petite body, she handed me my cell phone and said, “I programmed my number in; it’s up to you to call, but I hope you will.”
As we kissed goodbye I loved the way she had to stand on her tiptoes and stretch to reach my mouth with hers. I realized I could easily fall for her; besides the fact that she was an incredible lover, my heart jumped when she showed me her leather jacket and how she genuinely got excited when she found out I had a Harley. I more or less promised to show it to her and smiled when she begged me to take her for a ride, but it was more than that. It was her no bullshit attitude, her maturity and outlook on life, one that I’d recognize as being similar to my own.
A couple of days later I realized that I’d not yet begun to forget her face, but perhaps she was the one, and I shouldn’t. With that thought in mind I made a silent promise to myself; I’d call her and ask her out…soon.
* * *
Another week crept by and Jason and I chatted about every other day online; each time was beginning to sound like the last, ‘When can we get together,’ and ‘I can’t wait to feel you pound my ass some more.’
I’m not saying it wasn’t a turn-on for me, but it was a huge personal conflict within me. You can see how excited I got by the submissive way Jason acted towards me and the way he allowed me to be so controlling and dominant over him. The idea of dating Kym and seeing Jason on the side even appealed to me in some ways, and yet, I wasn’t so sure how either of them would react if they found out about the other.
I put Jason off that weekend, telling him I had a weekend ride planned that I wasn’t about to miss. He sounded disappointed, but understanding and I couldn’t help but feel as though he was becoming attached to me emotionally. I wondered if he was beginning to look at our relationship as more than just a friendship with benefits and quite frankly the thought sent a shiver up my spine. I was enjoying the opportunity to explore my dominant side while also learning why the thoughts of having sex with a she-male or submissive male turned me on so much.
On the other hand I knew deep down in my heart that I wasn’t gay; perhaps bi-sexual, but not completely homosexual. I knew this because of the way my heart was pulling me back towards the short blond kitten named Kym; after talking with her on the telephone for an hour each day for the past two weeks, I not only couldn’t get her out of my mind, I realized that I didn’t want to. After spending one night in bed and having a dozen conversations with her, I was hooked.
The next Saturday I picked her up on my bike midmorning and we spent the day riding through the Kettle Moraine area, occasionally stopping at quaint shops along the way. We had no particular destination and that seemed to be okay for us: I was just happy to have her near me and by every sign she felt the same about me. We stopped at an out of the way watering hole for lunch and were surprised to find a few people I knew there. When Kym went to the ladies room as I paid the tab, one of my friend’s wives leaned over and said, “She’s nice; don’t let this one get away.”
Later that night as the sun touched the place where the trees met the sky, our lips pressed hungrily against each other as our tongues practiced the tango to the soft music playing in our hearts. Compressing our bodies into one mass, I rubbed her pointy knobs with my thumbs as she became aware of my massive arousal. The she looked up and whispered, “I’d invite you in but, well…I have this friend who visits once a month, if you know what I mean.” I did and because I didn’t want to push her to do something about my hard-on, she kissed me goodnight, whispered a promise and sent me off towards home. As I roared off on my Harley, I remembered how she’d rubbed my crotch and said, “Take me out next Friday and we’ll take care of this for you.”
At the last minute, I figured I’d stop for a nightcap, but never made it inside the bar. When I shut off the bike I felt my cell phone buzzing, telling me I had a message waiting. I saw Jason’s number and thought sarcastically, ‘No big surprise,’ as I listened to the voicemail. It said his father was going out drinking and wanted to know if I could stop by. With my dick still hard for Kym, I thought of the duffle bag I’d left last week and headed off towards his house.
I shut down the engine as I coasted to a stop near to Jason’s place; it was just after midnight. I was making this up as I went, but had high hopes I could pull it off. Peering inside…all looked quite, but coming around the side of the house told me his old man had returned. Not one to back down from a challenge, I went towards the back door and seeing just the screen door I silently slipped within. I saw his father snoring away in drunken stupor, feet up in a recliner and an empty beer bottle on the floor. Creeping down the hallway towards Jason’s bedroom door, I figured my luck was running pretty high as I stepped inside his room and softly shut the door.
Watching the rise and fall of his chest confirmed he was sleeping on his back with just a sheet covering his body. I went to the closet to retrieve the duffle bag and set about setting up the scene as I withdrew my wrist cuffs, placing them one at a time upon first the right and then the left. Carefully, I fastened them to the headboard securely.
Next I take out three small pieces of a steel bar, screwing them together to form a single piece with clasps dangling from each end. Silently I fastened cuffs around his ankles; realizing he was waking up and there not being much I could do to prevent it, I withdrew a blindfold and quickly slipped it onto his head. Using gentle soothing tones, I instructed him to ‘be a good boy, relax and enjoy the experience’. Realizing it was me, he tried to comply as I grabbed the steel bar which spread his legs apart, tugging it towards the headboard, where I fastened it to the wrist cuffs with short 2-foot pieces of chain.
Quickly I undressed myself, allowing my hardening cock to pop free of my clothing as I admired my handy-work; Jason was hogtied and unable to move, although plenty able to struggle. Naked now, I reach for the video camera, placing it on a nearby chair. I pushed RECORD seconds after I pulled the ski mask over my head, focusing the screen to capture everything that took place on the bed, then stepped into view and reached towards his face.
After pinching his nose to make him open his mouth, I put my cock inside and told him, “Be a good little girl and suck Daddy’s cock.” He was such a submissive slut, he quickly set to sucking, and making slurping noises until I pulled it from his happy face. Next I climbed onto his bed...and then...let him feel the fat head of my cock as I placed it against his puckering pink anal star and held it there until he began to beg me to pound his tight hole.
I worried about his old man hearing us, so I bent forward and shoved a ball-gag into his oral hole, fastening it behind his head. Properly tied, gagged and blinded, I return to my former position, holding the bar in my hands to keep him from squirming around to much as I pushed my cock up his ass! Continuing to force my thick tool, inch by inch, into his butt-hole; I made sure to exaggerate the grunts and groans until my balls rest against his cheeks.
It was around that moment that I noticed his cock, normally a limp noodle, now beginning to inflate to a state of semi-hardness. I reached down with one hand and stroked his penis a few times and heard him moan through the gag while his body jerked a bit, too. Returning my hand to the spreader bar, I held his legs up in the air as I withdrew my prick from his tight tube...but only until I felt his flesh gripping it, secretly needing to be filled again. And that is just what it got as I refilled, withdrew and refilled his rump again and again...using this whorish orifice for my physical pleasure. I whispered to him, “I own your body, dear boy” and listened as Jason hummed affirmatively around the gag in his mouth. I could tell he was enjoying this pre-dawn rape fantasy as much as I was.
My plans were to pull out after fucking his sweet little hole for a while; to walk around to the head of his bed and stand above him; to release his gag, the blindfold and one of his hands so he could stroke my turgid dick until my cum first shot and the dribbled onto or into his mouth...but alas, plans sometime change at the last moment, don't they??
Continuing to pound his rear end until he felt my cock-head expanding as it does just before my balls boil, he shouldn’t have been surprised when my shaft erupted like the starting of a jet turbine; my slippery cum pulsing in giant spurts from my pipe, filling his deepest hole until it seeped from our junction point and slid down his crack to soak into the sheets!
After I came, I reached over and released the gag and blindfold, looking into Jason’s eyes and seeing his confused reaction to my ski mask. My cock was still as hard as a two by four; I watched his glazed-over pupils and heard his whispers of, “Please, please fuck me again.”
Ten minutes later, the scene has changed slightly...I'd released the bindings and put away the bar, the gag and the blindfold, but re-cuffed his wrists to his headboard. With him face-down on the bed, I mounted his cute little ass once more, using my spunk as lubricant to fuck him from behind for the second time. I whispered hoarsely, “Jason, your ass is completely mine and I’m going to continue to pound it until you’ve become useless to me, so you’d better try to stay in my favor.”
“I will try hard to make you happy,” he repeated as my cock sawed in and out of your enlarging anal orifice. A sliver of sunshine began to poke through the blinds and we both begin to shiver as another great and potent eruption took place inside his colon, the second load of my juice intermingling with the first.
Shortly afterwards, I crawled up along his body, held his head at the correct angle to my body and told him, “Clean my filthy stick, slut,” as I bumped the slime covered tool against his mouth. I could see he didn’t want to suck the cock that had so recently scraped the walls of his shithole, but making him do so was turning me on even more. My cock thickened as I once more pinched his nose shut and when he at last gasped for oxygen…I slid my dick onto his tongue and allowed him to breathe through his nostrils. “Now clean me or pay the price, cunt!”
While he did suck me, Jason did a less than satisfactory job of it and for that I knew my new found ‘pet’ needed to be taught a lesson. So I dismounted him, withdrew something from the duffle bag and knelt before him. “I’m going to spank your ass to show you what happens when a slave displays a petulant attitude to his/her Master. I want you to count off each time I swat you and ask for another. And Jason,” I explained with an evil grin, “you’d better make sure you ask as if you really want one or I’ll double your reprimand.”
As the long wooden spoon from my own kitchen landed on his pale white flesh, the sounds that echoed from his backside to the walls were a distinctive cracking sound. He proceeded to beg for more in his high-pitched, girl-like voice and I actually believed him, he was that convincing! By the time I let up, his body was reddened from his upper thighs to his lower back, with a few brilliant red stripes across his butt cheeks where I’d hit him exceptionally harder than the rest. Sweat dripped from my forehead to his flesh as he began to sob into his tear-stained pillow.
Carefully, I removed all my toys and refilled the bag, as he slowly sat up and watched me. When that was done I stood in front of him again, my cock blocking his view of the room. "Suck me, bitch,” I sneered, and then held his ears as I fucked his mouth slowly. When I finally began to feel like I could cum again, I removed the ski mask and told him to look up at my face; when he did, the black lens of my Nikon was looking back. His eyes widened as he let my dick slip from his face, so I slapped his cheek hard with my right hand and said, “Jack me off…I want to cum on your face.”
At first he actually looked upset, even angry that I held a camera and was recording the blow-job, but soon his fist became a blur as he sucked on the fat head of my prick.
“Put your finger in my ass, Jason,” I said. In a matter of mere minutes my third load spurt up his nose and into his mouth as I slapped his face with the spewing end of my stick. I wiped the remaining ooze from my softening cock into his hair, laughing and taunting him as I got dressed. “I’ll burn a CD and send you a copy,” I promised him as I held the camera in one hand and turned his bedroom doorknob with the other.
Of course what he’d soon realize would be my intention to do no such thing; these two hours of homemade porn was my insurance against him that our secret relationship would remain just that…a secret. His father still slept where I’d seen him before, so I let myself out and not too long afterward my head hit my pillow, a rotten sneer of sinful satisfaction on my lips.
* * *
The following Friday I took Kym out to dinner; a nice place she’d mentioned during a phone conversation a while back. She was impressed that I’d remembered it being one of her favorite places and also that I’d worn a tie. Later that evening when I took her home, unlike the last time we stood on her porch, she invited me in. The moment her front door shut I pulled her into my arms, kissing her lips more deeply than I’d ever kissed a woman and felt her responding in kind.
We never completely let go of one another as articles of clothing hit the floor on our way to her bedroom, where I lifted her tiny body atop her quilt and then we made love not unlike two people who were meant to be together, exploring every part of each other until at last exhaustion overtook us in the early crack of dawn hours. This time it hadn’t been about the screaming, multiple orgasms we each seemed hell-bent on giving the other, but more about drawing out the event until the two of us reached that highest of pinnacles in a chorus of crashing waves of ecstasy.
Saturday we woke up around noon and after sharing light breakfast and strong coffee, we made love in her shower for the second time; my hardness buried deep within her tight, young pussy as her fingernails cut into the flesh of my back. I found myself making excuses to hang around her place, not wanting to go home, but thought Kym was starting to notice. From the top of her short blond hair, past her perky breasts and stunning butt, to the tiny toes I’d sucked just hours ago…the thought leaving her made my heart ache. Finally she confronted me by stating, “You know if you decide to go home you can always come back later.”
When I said ‘really’ a little to quick, she giggled at my anxiousness, but confirmed my suspicions about where the two of us were headed when she finished with, “If you don’t I might just come looking for you.”
“Well then, maybe you should stay at my place for once,” I ventured. “What are you doing tomorrow night?”
With a sly look, that would later remind me of a cat that had just swallowed the canary, she looked up into my eyes and said, “I thought you’d never ask. Too bad it can’t be that tonight.”
When I looked heartbroken at hearing her last remark, she explained that she had to attend a cousin’s wedding that night, but that I shouldn’t worry because she was going stag. Not thinking about what I was getting myself in to, only looking for any chance to spend time with her, I invited myself to act as her escort.
With a look I’ll never forget, Kym looked up into my eyes and said, “You’d go with me, knowing that my family will be there; my parents, too?”
“Of course,” I told her, “as long as you save most of the dances for me.”
That evening, when she picked me up at my house, I noticed two items sitting on her car’s back seat; a wrapped gift for the bride & groom and a small overnight bag. Kym had been watching me glance into the seat behind her and giggled when our eyes met.
We spent the evening together at the wedding party; she introducing me to her parents, an over-protective big brother, a hundred cousins and a couple dozen friends. Once, she found her brother interrogating me and she told him to back off, remarking that ‘his little sister could take care of herself’. I thanked her for ‘coming to my rescue’ and then inquired as to the meaning of the term ‘little’ because her brother Mark didn’t look very old himself. I guess I’d never given it a lot of thought, although I could se she was younger than my thirty-five years, I’d never guessed she was only twenty-three.
“Why? How old did you think I was,” she asked.
“Honestly, I figured around twenty-six,” I lied, because I’d actually thought more like thirty but wasn’t about to let that secret escape. Kym only smiled sweetly and tugged me towards the dance floor. During a particularly slow one after dinner, no one could find the tiniest speck of light between our bodies.
She whispered to me, “Thanks for impressing my family so much; they think you’re a very nice man. My brother thinks you’re too old for me, as if you couldn’t tell.”
“I think your parent’s daughter is nothing less than amazing,” I said, lowering my chin against her own as we kissed passionately, not caring who was watching us. When the music stopped I finished my thought by telling her, “I hope they don’t mind if I do everything I can to hold onto their daughter for a long time.”
“I don’t care if they do or not,” she replied. Her big green eyes peered up through the semi-darkness into my deep blue ones and she tightened her grip on me. “I’m not letting you go, mister.”
Just an hour later she would decree, “You know this feels so right, that it scares me a little bit,” as we parked her car in the driveway at my house.
Corroborating her confession, I held my front door open for her and said, “You know that little bit of fear? Well, I think we feel that because our hearts believe that you and I may be soul mates.” I followed her inside, shut the heavy front door and took her hands in mine. If anyone had been watching, they’d not seen a single light come on inside as I set her bag on a chair and guided her to my bedroom.
* * *
The following three weeks passed by in somewhat of a blur, not that I don’t remember how the days were spent, but I say that because of how wonderful they were. During the times I wasn’t doing the things we all do to maintain or lives; working, sleeping and a hundred little things each day we do without thinking, I was somehow connected to this young blond nymph who had entered my life by accident just about two months prior.
That is not to say that Jason and I did not continue our communication via emails, the occasional telephone conversation and even see each other. He’d been very insistent regarding the film I’d made of him sucking my cock, so much so in fact that I eventually burned a copy onto a CD and left it behind his house for him to retrieve. Of course all that was on it was what he thought I’d shot; a short scene where he had a mouthful of my organ as he hungrily milked and moaned until I slapped it against his cheeks, shooting cum onto his face. The version he’d been given had no sound, unlike the full-length version I made multiple copies of.
There were nights when Kym had plans and I found myself drawn into the erotic world of the male alternative relationship that Jason and I had begun, although more often than not I began to think of excuses to avoid him. That was the beginning of his stalker-like tendencies and should have been a red flag to me, but I missed it.
I remember one evening in particular, when he’d shown up at my door under the pretense of wanting to talk and see how I was doing. Truthfully, the first thought I had was to invite him inside, tell him to remove his clothing, bind him to some object and punish him in the means of a good hard whipping! Perhaps because I knew the act would excite both of us, I’d pound his asshole with my cock until I came hard inside of it and then kick his skinny ass out.
On the other hand, I wondered if he’d secretly strategized coming over here when he knew I’d told him not to without an invitation first, as a way of orchestrating the evening’s outcome to end like that. Could he be so sneaky as to think if he blatantly disobeyed my instruction I’d give him exactly what he wanted? My mind wrestled with both sides of this argument long after I told him to leave and not return until I decided to initiate contact.
Furthermore, a more startling thought came to mind; if I was going to pursue something more permanent with Kym, my physical relationship with Jason would need to be ended one way or the other. I figured she’d not accept the thought that the man, who was even now charming her family and friends while winning her heart, was also hooking up with a submissive male friend for occasional fuck. When I put Jason on one end of an imaginary scale and Kym on the other, there was no doubt in my mind that she outweighed him by many fathoms.
Thinking back to that thought about ‘something more permanent with Kym’ was a subject filled with mystery and excitement all by itself. Later that night as I lie awake in bed, Kym’s nude body curled up against me, I realized that she and I we’re falling in love…but neither one of us was going to rush into declaring it.
* * *
Soon after that night, I’d asked Jason to come over to my place to assist me with attaching a couple of things to my Harley. I’d decided to put on a thick backrest and new passenger boards for Kym. When we were almost done the gears began turning in his head, asking me why I was making the passenger area of my bike more comfortable when I rarely had anyone on it. I explained that I was thinking of getting a large luggage bag and needed the backrest to help hold it onto the bike. Jason looked doubtful, mostly due to the way I’d made up the excuse in a hurry; I suspected he heard the hesitation in my voice.
When he began to ask a lot of questions about the back rest and luggage, I finally got irritated with him and spilled the beans, or rather I spilled a few of them. “Okay Jason, you got me, the truth is that I’m putting this on my bike to make it more comfortable for a certain young girl I’ve given a couple of rides to recently. She suggested it and I figured I’d give it a try and see, okay?”
“So you’re doing it for her? You, who doesn’t let anyone near your machine,” he squawked incredulously. “Just who is this girl and what does she mean to you?”
I was getting angered by his demands as he seemed to be headed for a major tantrum, but more so because he thought it was any of his business, so I grabbed the front of his shirt in my fist and shoved him up against the tool chest. “Listen here little man, it’s none of your fucking business who I see or what I do!”
“I’m so sorry,” he began, “I just don’t want anything to come between us; I like being your girlfriend.”
The meaning he put into the word ‘girlfriend’ I cannot clearly convey with mere pen and paper, but a scene from when I was in grade school flashed through my mind, taking me back to a time when I’d broken up with one girl to date another. That same tone was used by my then girlfriend when she’d used those same words just prior to crying on my shoulder. It had made me feel guilty back then; now it just made me feel sick, as I knew Jason might be capable of interfering with Kym and me.
When he stepped towards me and knelt on the floor with his head bowed, I knew he wanted nothing more than to suck me off and maybe take a punishment from me as well. It would be his way of getting what he wanted while allowing me the pleasure of my emphasizing dominance over him. But I had come to the decision that he would never feel my eight inch tool on his terms, so I dismissed him after I told him that ‘he hadn’t earned the right to service me today.’
Confirming my suspicions about his attachment to me, he asked if I wanted to come over later that night and punish him for his disobedience, but I simply said, “I’ll let you know when you’re needed, Bitch, now go home.”
Then he began to sniffle and cry, whining about how we had to work on a relationship to make it work and I began to develop a plan on how to end the relationship between Jason and me; sooner rather than later. An idea sprang into my head that gave me an evil grin. It revolved around his biggest fear involved with his sexual tendencies…the fear of getting caught.
Of course it wasn’t going to be easy, but I knew Kym was spending the upcoming weekend with her family, as they had a tradition started when she and her brother were young, of going to a lake resort up north for a vacation with just ‘the family’. She had told me about it recently while I was kissing her goodnight, “Maybe next summer you can join us,” she’d whispered. I’d answered her with a resounding ‘plan on it, babe.’ As I drove off I become conscious of the fact it was the first time in my life that I was contemplating making long range plans with a woman.
* * *
Over the course of the following week, I began to tease Jason mercilessly about getting to together to ‘pounding his ass’ as he so liked to put it. However I kept alluding to how I wanted to take it up a notch or two, to which he always answered me with a ‘whatever I can do for you’ type answer.
After speaking with the older brother of a good friend I knew, and taking that step of exposing my recent illicit affair to him, we hatched the plan which began with a simple set of instructions for Jason. If he failed to show then I could use that as an excuse to break it off with him; if he appeared as instructed and there weren’t any glitches, then I felt confident I’d have no trouble erasing him from my life once and for all. Of course my friend’s brother Tom, would then know my dirty little secret, but I had a plan for him as well.
First thing Thursday morning I jumped online to chat with Jason, making sure to mention how much I wanted to see him this weekend. He took the bait and began to go on and on about how horny he was, how he’d been missing my cock and the way he hoped he’d please me enough so that I’d want to fuck him good and hard. I smiled as I realized how easy he was going to make it for us. I told him that he was to check his email when we signed off; that he’d be getting a letter from me with instructions on it that were to be followed to the letter without question, and if they weren’t, the only retribution he’d receive would be the complete and utter disappearance of me from his life.
It was a simple choice: do what you’re told or give up the one you’ve grown so attached to. When he read my words, I could almost hear his sniveling in the words he wrote in reply. Quickly, I terminated the connection, opened my email and sent the draft that was meant to put my plan into motion. Jason,Over the past several weeks you have become closer to me than I’d ever thought a man possibly could. First you became my friend and then my Sub, who allowed me to fulfill my perverted desires. Now the time has come for me to judge whether you are truly my acquiescent bitch or if my needs can be better met by another; a more experienced boy than yourself. So I have devised a test for you to participate in, the summation of which will conclude with you either being chosen to remain in my service or you will be cast aside like a used tissue. Even the slightest digression on your part from the instructions will result in your instant disqualification, the consequences being swift and eternal. Remember, attention to even the slightest detail could mean a great deal. 1. For this exercise, you are to acquire two complete sets of women’s clothing to wear this weekend; you may use things already in your possession, but you will need: high heels, nylon stockings, panties, bras, blouses and skirts. 2. You will need at least one wig and something to stuff your bra with. 3. You are to dress in women’s clothing for the duration of this test, except when otherwise instructed. 4. All genital hair must be removed. 5. You are to be standing near the central fountain in the City Park at precisely 9:00 pm Friday night. Your feminine appearance should be sexy and projecting the appearance of a woman looking to get laid. 6. If approached, you will answer in soft, submissive whispers but will not leave the fountain area until I come to get you. 7. Until this test is concluded, you will remain submissive at all times.Do not fail me, my pet…I will be watching.
To say that the email freaked Jason out would be extremely understated. I ignored every one of his attempts to contact me via chat, email and text, but was truly taken aback when I picked up my office line and heard his voice on the other end. “Hey, it’s me,” he stammered. “I, I got everything you said, but…but I can’t go out in public like that! What if somebody sees me? What if my father found out?”
I waited for the silence on the line to grow and then simply replied, “If you can’t make it tonight, then it’s over between us.” I’d hung up just as he’d started to speak again.
After lunch I picked Tom up at his apartment and we drove out to his uncle’s isolated old farm, which stood alone just a few miles out of town. It was a shame really, by next year this whole place would be replaced with a massive expanse of blacktop and a new Wal- Mart Supercenter. But at least Tom’s aunt and uncle could retire and live the good life with the money they’d made on the sale of the land.
It was the perfect place for our little scheme and we finished setting it up much quicker than I thought. Fast forward three hours and I found myself sitting alone in my truck, the huge round fountain in City Park looming fifty yards off to my right, but appearing much closer through the binoculars. The water sparkled and danced in the air as the last few slivers of daylight sliced through the trees, giving the droplets a surreal appearance to anyone who cared to notice.
I’d been sitting here close to thirty minutes now…waiting…wondering if he’d show, betting he wouldn’t; shifting between my wish for this to end by his failure to appear and my distorted desire to see it through to the more, shall we say, erotic end. Glancing at my watch, I saw he was now a full fifteen minutes late and mentally made a note to give him fifteen more, when I saw him walking towards the fountain. I texted Tom and then settled in to watch the show for a while.
Jason was having difficulty walking in the heels he wore, but somehow it added to the scene because it caused him to step slowly and with purpose. Through the binoculars I made out his attire; thick clogs were easier to walk in and the way the glowing streetlamp bounced off his shiny legs, I knew he had on pantyhose under the snug fitting leather skirt. I wondered what he’d done to fill out the fuchsia blouse he wore nearly buttoned to his throat, because by all outward appearances he had a great set of tits.
To top it all off, there sat a wig of curly black hair that fell just past his shoulders, framing his face as he set down a shopping bag and stood nearby the fountain. I had to admit, he looked pretty good and I couldn’t help feel my excitement growing in my lap as I watched the scene unfolding before me.
A middle aged man appeared out of the brush and stepped towards him. Jason and the man exchanged words for a minute or two, and then the guy shook his head and walked away. I watched as he sat down on the edge of the fountain, looking around and probably wondering where I was since he was so late.
Tossing the binoculars into the back seat, I climbed out of my truck and headed off across the grass towards the center of the park, but just before I arrived, another guy appeared near Jason. I stood still in the shadows and tried to make out the conversation, but could only catch a word or two as they talked. Finally, the man said loudly, “Fine. Fuck you, you stupid whore!”
When he strolled away, I popped out from the dark side of the fountain, and said, “You look like a real whore, boy.”
He spun around, almost loosing his balance in those big shoes. When he laid eyes on me I saw such a look of relief I couldn’t help but bust out laughing, the scene was that hilarious…well, to one of us anyways! Then in a commanding tone, “Grab your bag and head that way,” I told him as I pointed back towards my truck.
A short walk through pitch blackness and we would arrive at the semi-lit parking lot where my vehicle sat, however when we reached the half way point I suddenly stopped. On a whim, I decided to change the plan just slightly as it occurred to me that Tom shouldn’t get to have all the fun. Stepping close behind Jason, who was panting more out of fear than exhaustion, I ran my hands down his ass and back up his blouse to cup his false breasts in my palms. “God, these look so real,” I growled as I squeezed the fake filled chest and ground my aching prick against his butt.
“Kneel down, you little cunt,” I told him, taking a hold of his shoulders and forcing him to his knees. When I stepped in front of him, lowering my zipper and withdrawing my firm rod from my pants, I whispered, “You know what to do, whore.”
He glanced about, obviously nervous already but even more now that he had to go down on me in the middle of a public park. Yet still, he performed marvelously until I blew a thick, swirling load into the back of his mouth. Next, I tucked myself inside my jeans and zipped up as I resumed walking towards my truck. I sipped my bottle of Pepsi, then took a bottle of soda out of the tray and held it out for him to take. “Here, I got you a Mountain Dew. I thought you might be thirsty after strutting around the park dressed up like a hooker.”
I backed out of the parking spot, telling him how I was taking him to a place where we could be alone. He was going to get his fantasy, his wish to have his tight asshole pounded over and over again. As he gulped down the drink his eyes began to glaze over; an observer might have thought it was from the happiness he felt within his beating heart, but I knew it was the drugs that I’d placed in the soda as I watched him drift into a state of semi-unconsciousness.
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<a href="https://www.lushstories.com/stories/crossdressing/jason-and-kym-part-two.aspx">Jason and Kym ~ Part Two</a>