1
Since getting divorced the previous year Glen had spent many days, weeks, and months pondering his feelings. Searching his heart for exactly what it was that he felt was missing from his marriage. Even during his marriage when things were still going well he had conflicting feelings about why certain things turned him on more than others. He had been married for twelve years and during that time had led a very fulfilling sex life. When he had first gotten married he had been what some would call vanilla. Not to be confused with inexperience, but overall had not sampled all the different flavors of his burgeoning sexuality. His wife, Lisa, who was seven years his senior, had managed to break him out of his shell and allow him to see that there is much more to a healthy sex life than inserting penis into vagina.
They had always explored each others body and had decided very early on that they would try anything at least once. So one night, about six years into their marriage, the topic of using a strap-on had come up. Of course this was something completely new to Glen. Not that he had never had his ass played with, quite the contrary, Lisa would indulge him very often while going down on him with a finger inside, massaging his prostate or occasionally sliding her tongue downwards and flicking at his ass hole with her tongue. Occasionally they had even used a small vibrator on him which drove him wild and he would usually cum within seconds of it being inserted inside of him. But the thought of her donning a rubber cock and fucking him like he did to her excited him very much. But what really made him question his feelings was the one night that she had taken complete control and had him get on his knees in front of her and suck the strap-on like the good little slut that he was.
Unsure of how to proceed he slowly got down on his knees, ok Glen, you’ve had this done to you a hundred times before, he thought to himself, you know exactly what to do. And he did. Slowly he wrapped his hand around the base of the rubber cock and inched forward until just the tip of it was in his mouth. Barely able to contain himself, he eagerly took the strap-on into his mouth all the way to the balls until he was gagging on it. Feeling his wife’s hands on his head as she fucked his face made him wild with desire and within minutes he had cum without even having his throbbing cock touched. Lisa, seeing the mess he had made, told him to get down and lick it up. Which he did without hesitation. That night had stayed with him for the many years that followed and led to their eventual divorce. So when he was home alone one night he figured it was time to explore these thoughts and went to Craigslist to check the personals.
He decided that it would be easier to post his own personal ad and see what takers he was able to find. So he posted a basic ad saying how he was a bi-curious divorced male who was looking to explore some feelings that he had been having for the past few years. It didn’t take long for the emails to start rolling in. He had settled on one particular response from a guy who was only twenty seven, ten years younger than he, who liked to crossdress. Being that Glen had a definite propensity for Transexual and Crossdresser porn he felt that this would be the one to go with, so he began exchanging emails that quickly evolved into texting. They made arrangements for later that evening where Glen would host. Feeling excitement that was relatively new to him, Glen began to get ready for the evening ny straightening up his apartment and then jumping in the shower.
2
Glen felt that it should be a casual night so after he got out of the shower he put on a pair of gym shorts and a t-shirt, figuring that if nothing else it would end up being a couple of guys just hanging out. Around nine o’clock Glen received a text that his caller had arrived. He had said in the texts that his name was Jaime which, Glen assumed, could go either way depending on whether he was dressed up or not. Glen had asked that it be a surprise and would leave it up to Jaime. Even though they had exchanged pictures Glen still wasn’t completely sure what to expect when he opened the door. What he saw was a tall slender figure with shoulder length brown hair wearing a long coat. What Glen didn’t notice were the high heels or the black stockings that were visible from the knees down. Glen opened the door and stepped to the side, ushering Jaime inside.
“Come in”, Glen said with only a hint of his nervousness showing.
“Thank you”, Jaime replied as he stepped through the doorway.
Glens front door opened into a stairway that went up directly into his living room. Jaime stepped past Glen and reached for Glens hand and led him up the stairs. His hands were as slender as the rest of him, definitely not the hands of a masculine person. With only a slight hesitation Glen followed. When they were at the top of the stairs Glen offered jaime a drink but before he was able to complete the sentence he took Glens face in his hands and kissed him. His lips were soft like you would expect from a woman. The kiss was soft, yet firm, Jaimes tongue slowly licking at Glens lips while gently pushing further inside until they were embraced in a full on passionate kiss. Glen could feel himself getting aroused, his cock getting harder. Jaime clearly felt it as well because Glen felt a hand slowly work it’s way to the front of his gym short and start rubbing his now throbbing cock through them. Glen could feel his gym shorts sticking to the tip of his dick with the pre-cum that was beginning to flow.
Jaime shoved him lightly down onto the couch and took a step back. He removed his long coat exposing a very form fitting black dress that came down to just above the knees. It was now that he noticed the black nylon stockings and matching black high heels.
“Do you like what you see?” Jaime asked in a sultry, not quite feminine or masculine tone.
Glen gulped, “I do. You have a very nice body.”
“Thank you,” Jamie said with a smile, doing a slow spin so that Glen could see the way the tight fitting dress accentuated his hips and toned ass.
Jaime stepped forward and reached down, grabbing Glens hand and placed it under the dress where Glen was able to feel the bulge in the panties he was wearing. Without saying another word Jaime pulled the dress up and over his head revealing a set of black lace panties and bra with matching garter belt holding up the black stockings. Glen could feel his cock getting even harder and couldn’t wait any longer. He leaned forward and began kissing Jaimes toned and hairless stomach, working his way down towards the bulge inside of the panties. He began kissing the bulge through the panties. He could taste Jaimes skin through the sheer lace. Slowly Glen pulled the panties down and removed jaimes semi-hard cock from between his thighs. He could see a small amount of pre-cum glistening on the tip and he instinctively licked it off. He lingered for a moment with his eyes closed as he savored the slightly salty flavor. Without removing his lips from Jamie’s cock, Glen began sucking gently on the head. He could feel the blood rushing into it. Wanting to feel it get larger inside of his mouth he took Jaimes entire shaft inside of him, gently massaging the sensitive underside with his tongue. Glen could feel the throbbing cock hitting the back of his throat but in his lustful desire did not gag or choke. Instead he pushed forward even further. He began slowly bobbing up and down, with his lips and tongue, taking extra care not to let his teeth touch. With his right hand stroking Jaimes now throbbing and engorged member Glen reached around with his left hand and slid his middle finger between Jaimes perfectly shaped ass cheeks and began to gently rub his tightly puckered ass hole. Jaime let out a moan of pleasure which only served to make Glen even more turned on. Taking Jaimes cock out of his mouth, Glen began licking the underside and looked up, eyes interlocking with Jaimes.
Wanting to push it eve further Glen stood up and pushed Jaime onto the couch, bending him over the arm. Standing behind him, Glen knelt down, spread Jaimes cheeks and began licking his freshly cleaned ass hole. Reaching around, Glen never took his hand off of Jamie’s cock. Glen was getting lost in the musty aroma of Jaimes asshole, savoring the sensation of pleasuring another man with his mouth. Glen was certain that his own cock was going to burst through the front of his gym shorts, but wanting to let the feeling last as long as possible he used every ounce of his willpower to not release it from the confines of his shorts. The lust he was feeling only fueled him more and he dove entirely into his task at hand. He could feel Jaime’s hand on the back of his head pulling Glen into him. Glen was slowly working his tongue deeper inside of Jaimes ass hole and Jaime was loving every last second of it. Glen, wanting to taste Jaimes cock again pulled it back between his legs and began sucking it from behind. Now that Glen was no longer focusing on his ass, Jaime reached back and began fingering himself, first with one finger, then working his way up to three. Glen eagerly sucked on jaimes cock, using his hands on Jamie’s hips to pull him backwards then pushing him forward again. Glen could feel Jaime start to gyrate his hips in rhythm to Glens sucking motion. Without warning Jaime came, erupting inside of Glen’s mouth. Glen, not wanting to disappoint, swallowed every last drop, and continued sucking making sure to not let a single drip of cum go to waste.
3
Shaking in post orgasmic ecstasy, Jaime stood up and sat on the couch, patting the seat next to him, motioning for Glen to sit down. As Glen sat down, Jaime leaned in to kiss him. Again, Jaimes tongue was inside of Glen’s mouth, no doubt tasting his own cum. This thought alone made Glen even harder which he thought couldn’t even be possible. Sensing the urgency, Jaime got down on the floor in front of Glen and slowly pulled his shorts down finally exposing his very girthy cock which, at this point, was shiny with a covering of pre-cum. Glen was certain the minute his dick was touched he would cum, but much to his surprise as Jaime took Glens cock into his mouth, he did not cum. Glen could feel Jaimes tongue working the underside of his cock then as his lips reached the tip, would circle around the head before moving back down the shaft. Jaime would repeat this process over and over again. It was a sensation that Glen had never felt before. Jamie’s tongue felt like another appendage with how expertly he used it. Pulling Glens legs up onto his shoulders, Jaime pulled Glen forward until his ass was hanging off of the end of the couch. Without saying a word, Jaime pushed Glens legs up and began tonguing his asshole.
Once Glens asshole was nice and lubed up with spit, Jaime went back to sucking on his cock. He slowly worked his middle finger inside of Glens asshole and quickly was able to find his prostate. With the precision of a doctor, Jaime was able to massage Glen’s prostate and get the pre-cum flowing like a faucet. Glen could barely stand it at this point. He had had his prostate massaged before, but never like this. Glen was at a constant state of near orgasm but anytime he felt like he was about to cum, Jaime would stop. It was as if he somehow could sense everything that Glen was feeling. Jaime put Glens legs back down but continued to service him. Now that Glen’s legs were down, Jaime was looking up at him, their eyes locked together. All of a sudden Jaime stopped, stood up and held out his hand for Glen to take.
“Take me to your bedroom please.” Jaime said.
Without a word Glen stood up and led her into his bedroom.
Once in the bedroom Jaime told Glen to lie down on the bed, which he did. Jaime kneeled on the bed at Glen’s head, straddled him and laid down putting them into the sixty-nine position. Jaime then proceeded to take Glen’s cock into his mouth again. Glen followed suit. Now that neither of them were inhibited by the confined space of the couch, they were free to move around a bit more. As Jaime was continuing to do that amazing tongue trick he was slowly moving his hips up and down, gently face fucking Glen. The feeling was incredible and soon Glen was on the brink of cumming only this time Jaime did not stop, but instead began bobbing his head up and down more vigorously while at the same time quickening the pace at which he moved his hips up and down. Glen could not hold it in anymore and released his full load into Jamie’s mouth which he took with much excitement. Glen could feel Jaimes tongue and throat swallowing his seemingly endless load. Just as Glen was finishing cumming he felt Jaimes muscles tighten and knew he was about to cum again. Glen reached his hands up, and placing them on the small of Jaime’s back pulled him into his mouth as far as he would go just as he released in Glen’s mouth. Once again Glen gladly and eagerly took it all, swallowing it like a greedy animal, all the while Jamie’s mouth had not left Glens cock.
Jaime turned around, and crawled on all fours where he collapsed on the bed next to Glen. Both men slick with sweat, they laid together, gently caressing one another. Jamies hand was very gently and slowly playing with Glens now flaccid cock, occasionally getting a small drip of cum on his finger where he would bring it up to Glen’s mouth and have him lick it off. Soon they were kissing again, although this time in a more sensual, and less lustful way. Glen could taste his cum, cock, and ass on Jamie’s lips and it was starting to arouse him once again.
Jaime looked at glen with a smile and asked, “Would you like a massage?”
“Mmmm”, Glen moaned, “I would love one.”
Without missing a beat Jamie was on his knees and had rolled Glen onto his stomach while at the same time straddling him at the thighs, just below his buttocks. Jaime began massaging Glen’s lower back, working from the spine out, then working up towards his middle back. As Jaime got further up Glen’s back and was leaning forward more, Glen could feel that Jaime was getting hard again and could feel it pressing against his ass. While having actual penetrative sex was not something he had been wanting or expecting to do tonight, the thought of having Jaime inside of him was beginning to arouse him. Glen could feel his own cock filling with blood again. In an attempt to get himself more comfortable with his growing member he moved his hips around, attempting to adjust himself. Jaime took this as a positive sign and began working his hands down his back again. Once he got to the small of Glen’s back he continued downwards and began massaging his buttocks, using his thumb to gently rub Glen’s ass hole. Jaime proceeded to kiss up and down Glen’s back, each time moving lower and lower until he was kissing and licking the very top of his crack. Jaime moved down, and spreading Glen’s cheeks, began flicking his tongue over his ass hole. Glen was quietly moaning and gyrating his hips in absolute ecstasy as he was being rimmed once more by Jaime who was now working hi way back up towards Glen’s shoulder with his tongue. As Jaime reach Glen’s shoulders, Glen could feel the tip of Jamie’s dick rubbing on his asshole. Jaime reached down and very gently and slowly began working his cock inside. The sensation at first was startling and it made Glen jump instinctively. Glen asked Jaime to just wait a minute and he would push back slowly and at his own pace.
It took him a few minutes of easing back and forth but soon he felt jamie’s stiff cock slide inside of him and Glen let out a shudder of pure pleasure. Holding Glen’s wrists by his shoulders, Jaime began pumping. Long, slow strokes. With each slow thrust Glen could feel jamie’s cock hitting his prostate. Jaime began to pick up his pace, thrusting faster and harder while Glen met each downward thrust by pushing back into him as best he could since Jaime was still lying flat on top of him. With each thrust Glen could feel Jamie’s hot breath on his neck and it was driving him insane with pleasure.
“I’m going to cum inside you,” jaime whispered in Glen’s ear, “I’m going to fill you up with my cum. Would you like that?”
All Glen could get out was a whimper so instead he answered in the affirmative by pushing back into Jaime. Glen could feel Jamie’s breathing speeding up and his thrusting was matching it. Soon Jaime was pounding away at Glen’s virgin asshole, Jaime pushed himself up on his hands and with one final thrust released inside of Glen. Glen was amazed at the sensation of feeling Jamie’s cock pumping hot cum inside of him. He could feel each pulse as another shot of cum was emptied into him. Eventually jaime was spent and collapsed on top of Glen, taking a moment to regain his breath before rolling off of his back and pulling his slowly deflating dick out of Glen’s ass. Immediately he could feel Jamie’s hot cum begin to drip out of his relaxed asshole but before he could do anything about it Jaime was down there wiping him up, cleaning his own cum off of the bed and between Glen’s ass cheeks.
Glen rolled over onto his back and stared at Jaime who had a sheepish grin on his face. Jaime began stroking Glen’s dick, using his own cum as lube. Jaime would reach down between Glen’s legs and would run his middle and ring finger up Glen’s crack, scooping up what cum had dripped out and use it to lube his shaft. Glen just looked up at the ceiling, closed his eyes and enjoyed every second of this incredible handjob. With his cock completely lubed up with Jamie’s cum, Jaime once again straddled Glen only this time he slowly lowered himself onto Glen’s cock. He began to ride Glen’s slick member, moving his hips forward and backwards. Glen looked down and watched the muscles in Jamie’s abs ripple with each movement. This was the first time all night that Glen was able to truly focus on what Jaime was doing since Glen was actually facing him and Jaime was doing all of the work. Glen put his hands onto Jamie’s hips and helped move him along. He looked down at his own stomach and was mesmerized by the view of seeing jamie’s semi hard prick moving along, a stream of clear pre-cum clinging from the tip of it to his stomach. Judging by the moans escaping Jamie’s throat, Glen’s cock was hitting all the right spots. Glen could feel himself getting closer. Never before had he cum so many time in such close proximity to each other. He closed his eyes and focused on Jamie’s rhythmic movements, trying to time his own as to be in sync with him. All of a sudden he felt something hot and wet land on his chest. He opened his eyes in time to see cum shooting from Jamie’s cock with each forward thrust. Amazing! Jaime had cum yet again, purely from prostate stimulation. Feeling Jamie’s hot cum land on his chest he moved his hands from Jaime’s hips to his own chest where he began smearing the cum all over himself and licking his hands clean.
Putting his hands back on Jaime’s hips he began moving him along faster while bucking his own hips up and down. Glen pulled Jaime down to him and kissed him, shoving his tongue deep inside Jamie’s mouth. Never before had he felt such a passionate kiss. He could still taste and smell himself on Jamie’s lips. Pulling him in even harder Glen thrust up once last time and came harder than any other time that evening. He quickened his thrusting, pumping harder and faster until he was done and had filled Jamie’s ass with what felt like a gallon of hot cum. Jaime collapsed on top of Glen and they both rolled onto their sides, legs and arms intertwined, still kissing and tasting each other and themselves on the others mouth and lips. At some point Glen drifted off to sleep. When he awoke in the morning Jaime was gone. No goodbye, no note. Glen could still smell the sex in the room. Closing his eyes and thinking back to the night before, he began stroking his cock.