1 comments/ 23305 views/ 11 favorites Secret Rendezvous By: Rhynovampire There was only one person that knew my need, my ex-wife and she is sworn to secrecy. My girlfriend, Karen, would freak and probably throw me out if she found out. When I was married, at least years into it, our desires began to come out, even though they weren't acted upon. I wanted it once, I needed it just once. The want to feel and see what it was like to sleep with a transvestite started to overwhelm my every thought. Jerking off to videos was getting old, reading stories just didn't fulfill it. Karen left for the weekend to see her sister in N. Carolina. Now was my opportunity. So I went online to find an old friend, one I had met on a kinky chat room when I lived with the Ex. We had gotten to know each other quite well, each others real name, what we wanted out of relationships and so on. Amy lived in the South Jersey, two hours from where I lived. I had sent her an email with my phone number and asked her to call when she could. "Hello?" "Amy? It's Charlie," his nervous tone could easily be heard over the phone. "Well hello stranger, how are you?" "Not too shabby, can't complain. Mind if I ask you something?" "Sure ask away, you know I'm an open book." Confidence was never as issue with Amy. "I'd like to meet with you. To....," then came the hesitant, fearful chuckle whenever I couldn't come up with the words. "Are you sure? You know I've wanted you for the longest time." "Yeah, I'm ready. You only live once right?" "Definitely Sweetie, you know that resort out in the woods I've told you about, the one with the pool in the room? The reservation will be under Amy. Meet me there at 4." "Alright, thanks darling." "Anytime handsome, I want you to fuck me good." "I'll do my best. See you there." After hanging up the phone, I packed a duffel bag with a change of clothes, and then headed out the door. During the entire ride up the highway, the hard-on that my fantasies provoked practically touched the steering wheel. The Coliseum Resort was an hour away. It had themed rooms, each with an 8' by 10' pool inside of it. It was 3:30, so I checked in and asked for Amy. "Room D-21," the receptionist said with a welcoming grin. "If you are in need of anything please do not hesitate to ask." "Thank you." I smiled back and took the keycard. Down one hallway then another until I reached D Wing, then at the end of the corridor was Room 21. Sliding the card down then up, the latch to the door unlocked. Once inside, I dropped my bag and looked around. Walking from the sitting area into the bedroom I could hear someone. "You are punctual aren't you, handsome." "Sorry, I expected traffic coming up here. I'm not one for being late." "Good." she responded with an evil grin. The vixen was coming out in her. As she approached all the fantasies I have had were coming to life. Amy was just a bit shorter than me. Blue eyes, red lips, black hair, Size-D breasts and graspable hips made me shiver, yet I couldn't to move. Walking around me slowly, she took in a breath of my cologne and kissed my neck. My reaction was to close my eyes and let out a soft breath, the bulge in her dress caressed my ass. "You will remember this night for the rest of your life Charlie", she whispered into my ear. "I know." I did my best to calm down by taking long full breaths. From behind she slowly undid the buttons of my shirt and yanked it from my pants, leaving me bare-chested. Her teeth would occasionally dig into shoulder, followed with a lick by the tip of her tongue. "I've wanted your cock since we first started role playing Charlie. I promise to be gentle." "I can't make that promise, that's how bad I want it." "You're a rough boy, hmmm?" Amy put a hard slap to my ass, so I reached behind to find her cock and get a good hold of it, she whimpered from my touch. "Pool first?" she asked "Yes I want to see you wet." She came back around to the front and immediately took her jet black hair out of its ponytail. That alone would give me a hard on. Her green blouse that revealed just enough cleavage was taken off over her head so I could see a hunter green lace bra. A black knee high skirt was unfastened and let to fall to the floor at her feet. I let out a soft growl, as all that was left was a pair of matching panties. Following her lead, my pants were unzipped and kicked to the floor with my shoes and socks, but 'I' took my boxer briefs off. "My favorite color," I said while staring. "I remembered," winking at me while in a lustful pose. Walking a few feet to her right and down a set of three stairs was the pool, enclosed in a glass room to keep the heat in. Stopping at the edge, she turned, smiled mischievously and then went down the ladder into the pool. The moment her feet touched the bottom Amy went under, her hair was even blacker and sexier once it was flat to her back. "Don't make me wait", she beckoned. Getting in slowly, I could feel her watch every one of my steps. Once I'm in the water I turn and her lips leap at mine for a long lustful kiss. Our arms scanned over each other's body, mine held tightly to her ass, ours cocks teasingly sliding against each other. One of my arms gripped her soaked locks and yanked on it hard to pull her head back, so my kisses could be put to her neck and shoulders. "Fuck, I want you", I said. "Oh I can see that?" one of her hands wrapped around my cock completely, toying with the head then moving along my shaft. Before I could let go of Amy's hair she slid down my chest and under the water. Her hair hid what I could see from above but I could certainly feel what she was doing. Those gorgeous red lips engulfed my cock to where I could feel my tip graze the back of her throat. My animal instincts took over; both my hands grab the back of her head and pull her head towards my stiff dick. Amy gagged on it since I could see the bubbles come up to the surface. She came up for just a moment to say, "Give it to me bitch." Taking in enough air, she then went back down, this time her hands held my ass cheeks and spread them wide. A finger journeyed around my cheeks and poked my brown hole. That finger went one knuckle deep while I controlled Amy's head. When it got to the second knuckle, I yanked her up to give her some air, then dunked her back down to finish me off. That middle finger is now fucking my ass, as my balls are filling with cum. "Oh no Sir, not yet", she came up and the finger released my ass, "Your turn". Amy then took charge and pushed me under, my hands pull down her panties to release quite a massive hard on. It seemed about the same length and girth of mine but hairless. Amy was shaved from head to toe. My lips touched it, and then opened to take in just the head. My heart raced as I went for it, opening my mouth and throat to swallow it whole, my needs took over. Sucking her cock came natural all of a sudden. I didn't care for the stigma, just what made me happy and I was taking it, I became Bi at that moment. Letting me up, I put those lips right to hers, "That was amazing Amy." "Good, I knew you were a keeper." She then turned around; the crack of her ass was put in perfect position for my still raging hard-on. "Are you ready to fuck me, Charlie?" First, I reach behind for the waterproof lube and coat my cock; the other hand went between Amy's shoulder blades to push her forward and back under the water. My tip was lined up and slid in gradually to allow both of us to adjust, her ample hips allowed me to get leverage and pull Amy towards me. Her asshole overwhelmed the cock that went into it. Every five or six thrusts, Amy would come up for air, and then go deeper in the water, changing the angle and the depth at which my hard-on could go. "Fill it, fill it Charlie, load up my ass with it." My thrusts became furious, with a few more deep penetrations my load came out of my balls, through my dick and into her ass. "FUCK!!" A few seconds later she swims away to the opposite edge to come up and smiles directly at me. "That was nice. Now come to me," a finger summoned me. Gingerly I went to her, because I knew what was coming. She reached under for my legs and put them over her shoulders, I was now floating, open and willing to be fucked. She used that same lube and pushed down by my hips, putting me underwater in the process. Amy's thick wood penetrated me with ease; but a scream still went to the surface. She would not wait, plunging her cock into my asshole feverishly. Ten or twelve pumps and she exploded into me. My legs came down to the pool floor after I caught my breath. Amy kissed me slowly and I returned it just the same. "I want you again Amy. Karen won't be home until Sunday. I am here for the night" "Then I am glad I brought my bag of toys, hmm?" Secret Rendezvous BTW, this is going down as one of the top contenders for an exciting/hot scene/hook up. He is a regular lover that I only get to see every so often. I was told to wear a skirt (I added crotch less panties, and half cup matching bra) and to show up at 10, go straight into the garage. I arrived, went in, and there was a chair set sitting to the side in the room. I sat in it, sent him and text that I had arrived and waited. He arrived shortly thereafter and immediately walked up to me, kissing me and squeezing my nipples. Shirt was removed. I was then asked if I minded being handcuffed. I didn't mind and was excited to be asked. That at that moment I knew this was going to be a very surprising fun night. He was going to surprise me with something more my style. He stood between my legs, forcing them open. While kissing me he lowered his arms/finger and found his way to my already wet clit. He fingered me and I almost immediately came. I could see he was hard, his cock was sticking out of his pj bottoms, just begging me to suck it. I asked if I was allowed to suck his dick while he stood in front of me, me sitting in the chair. He would occasionally bend down and finger my wet pussy; run his nails down my back, take his dick out of my mouth and slide it around my face, slapping me a few times with it. Getting me off with a few small orgasms with his fingers. The hornier I got, the more he could squeeze and bite my nipples. After a few minutes of this foreplay, he grabbed my hand and holding it he told me to follow him. Holding my hand was shocking enough. I was focusing on that, didn't pay attention that he had walked us to another part of the garage.. There was a rigging set up; a secure strap with a release and hook hanging from the ceiling beams. At the very end was zip cuffs attached by the hook. It was perfect! When I figured out what was going on, I was so excited. Giddy like a school girl. I think I hid my excitement, I try not to annoy him with silliness (not that he has ever complained, I just always feel a tad bit nervous and enjoy playing the part of keeping quiet and obeying his orders. Can't say I'm that great at always following directions and not whining about one thing or another; i.e. the position is hard to do, I feel awkward, don't trust in his commands or knowledge). It could/was lowered into all different heights, for different angles. I slide my hands through the loops. I could then intertwine my fingers and lean over. He positioned himself behind me and fucked me from behind. After a while the rope was lowered and I was bent far over, with my ass in the air. He could fuck me from behind while slapping my ass. He could also find a rhythm; lean back and watch his cock slide in and out of my pussy. We could hear him slide in and out, my pussy was soaking wet. Slurping away on his hard cock. I came several times. Squeezing around his cock before drenching him in my cum. Over and over again He would ever so often wrap his arms around and squeeze my nipples. Using my boobs as leverage to fuck me harder. At one point it was feeling great and we were really going at it, he took his hands/fingers and put them in my mouth, holding my mouth open and as leverage while he fucked me. It was so hot. I know I was gushing at that time. My pussy was on fire. He wrapped his hands around my skirt that had been bunched up around my waist on the sides and used it for leverage to pound me harder. That was also a very hot point, I loved the aggressive behavior. He then brought over the chair and sat down in it. Having me straddle him, cowgirl style, and lower myself onto his hard cock. I could keep my hands/wrists on the cord and use it as leverage to fuck him. (BTW, this is the part when I realize I need to fucking get in shape. My stamina and strength is for shit. I need to get some legs muscles and slender them down just a tad bit). This felt great, the position put him deep inside me. I could get aggressive and slide back and forth, feeling his balls bounce up near my clit, I could pull myself up and down on the rope, fucking him quick and pounding into him, I could also lean back resting my arms behind me on the chair arms. This gave him access to my clit (would be so much easier if I lost just a little more weight, easier to wrap his arm and reach down to my clit). I could cum easily this way, squeezing down on him. I got off several times, finally bringing him to his own orgasm. He got to cum deep inside me this way, while I rode him. After he finished inside me, I got to lower the skirt and get dressed. I left soon there after and went straight home to write this up so I wouldn't forget it really did happen. It was such a special gift. I've always wanted to mix the bdsm and sex. It was so fucking hot. I couldn't believe he was doing all this for me. That he had taken the time to rig it all up and come up with these positions. It was a truly amazing gift. I couldn't believe someone would take the time to do something so selfless, something just for me. He (in the past) has been pretty uninterested in the bdsm concept and was more of an open minded vanilla lover. I sure hope that I some how make him happy. I've no idea how to show my appreciation for such acts of kindness/excitement. *some small edits due to story version written rather than a timeline of events. Secret Rendezvous They hadn't seen each other in years, but they'd recently rekindled a strong connection over their many conversations online. They'd dated briefly after high school, but now they were closer than they'd ever been, despite the distance between them. Jess walked nervously out to her Jeep, the slight breeze tugging at her short skirt. She wore nothing underneath it, so she was instantly self-conscious at the weather's playful mood. Her sumptuous, round breasts filled her tight button-up shirt almost to bursting. She had piercing ice-blue eyes and wild, dark curls, tied back away from her stunning face. She had all the right curves, in perfect proportion to her medium height. Taking one last cleansing breath, she put the Jeep into gear and pulled away from her house. Her oblivious husband wasn't even aware she had walked out the door. It had been that way for far too long, and she finally decided to think of herself this one time. Sam pulled into the parking lot where they'd agreed to meet, a local all-night diner. He'd been in town for more than a week, having made the 500 mile drive from home to visit friends and family, but this was the first chance Jess had to get away. Tonight was a long time coming for both of them, and the anticipation he felt was killing him. He shut off the car and stepped out into the mild summer air. It was still warm, as might be expected from a summer night, but the relative coolness of the breeze was a refreshing change from the sickening humidity of his adopted hometown hundreds of miles away. He smoothed the chest of his dark polo shirt and absentmindedly brushed the legs of his tan cargo pants. It was a bit of a change from his usual t-shirt and jeans, but he wanted to step up his game for the stunning beauty coming to spend time with him. He thought back to how he came to be in this parking lot, awaiting her arrival. In almost six years since he'd moved out of state, this was his first opportunity to travel back home alone. Usually his son made the trip with him, but this time the boy was away at summer camp for the first time. Sam's wife stayed home as she always did. They'd stopped traveling together long ago...in fact, they'd stopped doing nearly everything together years earlier. These days, it seemed the only two things they shared were parenting responsibilities and a home address. Sam's marriage was just as dead as Jess' was. He looked out and saw headlights approaching. Her headlights. His heart began racing. She saw him standing by his SUV, and she swallowed nervously. Pulling into the parking space beside him, she shut the car off and stepped out. Walking around, she stepped between their cars where he waited. Their eyes locked, and without a word they were in each other's arms, kissing deeply. Sam could feel his cock stiffen as Jess pressed herself against his body. She felt it too, and slid her hands down to release his thick member from its constraints. Her fingers sought out its veiny texture as she gripped it. She stroked it, feeling it throbbing rhythmically in her hand. Sam pulled Jess closer, his strong hands sliding down her back and across the soft curve of her ass. Suddenly he spun her around and pulled her close. His hands gently lifted the hem of her skirt as his pulsing cock pressed into the round fold of her soft butt. He kissed and bit her neck, his two-week-old beard scratching her tender skin. A gasp escaped her lips as her hands reached up and stroked his clean-shaven head. By now she was soaked, and she felt her sweet juices trickle down her leg. The anticipation was unbearable. Without a word, she willed him into her, and somehow he got the message. With one hand on her hip and the other pressing the soft spot between her shoulders, he bent her forward as his stiff rod pressed effortlessly into her dripping cunt. God, he felt huge! Her first orgasm came out of nowhere, and she was shocked at its strength. Her knees buckled and she nearly fell. As he pistoned in and out of her, he felt her pussy squeeze around him as she came. She almost collapsed, and he struggled to keep her on her feet. Suddenly he withdrew from her and climbed into the back seat of his massive SUV. Jess didn't follow him immediately. Instead, she undid the buckle on his belt, opened his pants the rest of the way, and pulled them to the floor of the truck. Climbing in to join him, she straddled his lap and slowly lowered herself onto his stiff cock. As he filled her still-throbbing womanhood, she bit her lip and pressed her forehead to his. As she rode up and down his thick member, she leaned over him to feel the roughness of his beard against her neck once more. She couldn't get enough of the sensation. His hands lifted her ass and lowered her down to his lap, over and over. Slowly his fingers found their way around to the tight, forbidden hole between her buttocks. He felt her twitch at his gentle touch, heard her gasp. As he carefully pressed a finger into her ass, he felt her slick cunt squeeze his prick once again. His balls tightened as his orgasm started building deep within his groin. His other hand slowly climbed up her back and cradled her head as he pressed her closer to him for a deep, longing kiss. He gripped a handful of her hair and gently tugged her back, away from him, arching her back. As her breasts pushed toward him, he released her hair and quickly unbuttoned her shirt, freeing her large, round tits. Her lacy black bra was straining, and he deftly undid the clip in front, releasing her breasts. Her nipples called to him, and he answered with his tongue. He bit her lightly, and the sudden, sharp lightning strike of sensation coursed through her tender nipples and made her ride him harder and faster. Without warning, his cock erupted in orgasm, and he pressed into her as deep as he could go. His cum flowed in pulsing waves, filling her. She felt his warmth pumping into her as her sweet pussy squeezed and released, drawing more of his seed from him. Spent, they simply held each other, Sam's warm cum spilling from Jess' soft cunt. Their labored breath was perfectly synchronized, as their hearts gradually slowed to a normal rhythm. They pressed their foreheads together again, their eyes locking once more. She smiled at him as they both realized neither of them had said a word since meeting here in the parking lot. They hadn't even made it to his hotel room yet. It would be a long, exhausting night indeed, and neither of them expected to get any sleep.