Panties, Porn and Bi Pleasures Ch. 02

Note: All characters in this story are over eighteen years of age.

It was a long week of anticipation for Jack. He had made love with his wife, Beth, on three occasions. It was purely “vanilla” sex: She was only willing to fuck in missionary position, with limited foreplay, no oral – neither giving it to him nor wanting it from him.

The incentive was not the “act” with her; but, rather it was the thought of his upcoming game day date with Chris. Although Beth was a fairly attractive lady, Jack could not finish without some other fantasy assisting. The boredom of repetition was just too much. When he flooded her hairy cunt with his load, it was Chris, panties and porn that drove him over the edge.

Of course, Beth was curious about Jack’s suddenly increased libido. He responded by telling her, “Getting out more, as you have encouraged, seems to be helping!” She accepted his explanation and was happy to get the increased frequency.

“I am going to visit sis tomorrow. I will be staying over until Sunday night. If you want, you can invite Chris over to watch the games.”

“Sounds good to me, Beth. I hope that you have a good time with Jill!” He quickly texted Chris, inviting him to his home turf.

That night, Jack snuggled lovingly with his wife and he drifted off, thinking of his meet-up the next day with his new intimate acquaintance.

Chris also spent the week in great anticipation of the upcoming weekend’s activities with Jack. He did not have another sex partner, but did regularly use his expensive sex toy. Her name was “Anastasia”: A very realistic doll, with soft, elastic TPE material, perky B cup tits, and a lifelike “cyberskin” vagina. He also opted for the “shemale kit”, which turned the young female doll into a nicely-dicked trans female.

Months after losing his wife, Chris found many advantages of a love doll: She was always ready; she didn’t complain; and, after the initial investment, she was much cheaper to maintain. Most times he used the doll’s female features, preferring her tight vagina. Unloading inside her sweet asshole or nice mouth were also hot for him. He had experimented with the insertable penis a few times, but never took it inside – that is, until the past week.

Since last weekend, Chris had fantasized about having Jack’s sizable cock buried deep inside his tight ass. The thought of that possibility was too much for him, and, on Thursday night, he felt like he had to have Anastasia’s trans cock inside him. With the aid of plenty of lube, he managed to get the doll dick inside, “reverse cowboy” style. After getting used to the feeling, he squatted down more. He rode the rod for quite some time, while stroking his hardness.

With his prostate being assaulted, he could not hold back any longer. He spurted a massive load across the bed and on the doll’s sexy black stockings. Chris fell back atop Anastasia, balls entirely drained.

The next night was more of the same, but he also dressed in a thong, garter belt and stockings. After getting a good ass fucking from the doll, he assaulted her tight asshole, ultimately filling her rear cavity with his hot semen. As he laid beside his fuck mate, Chris got Jack’s text. He responded, “I’ll be there by noon.” As he pressed “send”, his heart raced, thinking about all of the possibilities for the following day.

The sun was shining brightly on Saturday morning. Beth kissed her husband and headed east, about 300 miles away, to visit her sister. Jack was straightening up the living room, and later, preparing guacamole, salsa and chicken wings.

It was already 11 a.m. and it occurred to him that he had not even picked out his panties yet. He had several options laid out neatly across the king bed: a solid light blue thong; a transparent black bikini; a red silk, lace trimmed pair of “sissy” panties (open back); and a bright orange pair of lace cheeky panties.

Jack enjoyed trying on all of them, before deciding on the transparent bikini. He had gotten quite an erection and his shaft was well defined in that pair. He really wanted the “sissy” as first choice. However, he was not sure about the message that it would send to Chris. He feared that the open rear might be an invitation for rear entry – something that he was not quite ready to do. He admired his panty-covered boner in the mirror one last time, before donning his jeans and T-shirt.

The doorbell was chiming as Jack finished dressing. Even though he wanted to hurry, he was very careful zipping up, lest he snag his pretty undies. He greeted his new playmate at the door, and invited him inside, smiling widely. Kurtköy Escort “Chris, an overnight bag? I didn’t know that you were planning to sleep over here tonight, but it’s OK, if you would like.”

Chris walked over to the plush sofa, dropping his bag on the floor. “Actually I hadn’t thought of that, but would be happy to stay over! I have a surprise for later in this bag.”

Jack responded, “I hope that later comes soon! Gotta be a hot surprise!” He walked into the kitchen, retrieving the food. When he returned, Chris was on the sofa, taking off his shirt. “Damn, Chris, I thought we would wait until at least halftime. The kickoff is still fifteen minutes away!”

“There’s no rule about getting comfortable first, is there?” Chris joked.

“Nah, I guess not!” Jack answered. He put the food tray on the ottoman and stripped off his T-shirt. “At least we won’t have to worry about wing sauce on our shirts, Chris!”

“Well, Jack, I know you have pretty good sauce!”

“As do you, my friend!”

Both men chuckled as Jack sat close to Chris on the sofa. The jean-clad pair began to devour the chips, dip and wings as the game started. The two were quite a contrast physically: Chris’ smoothly waxed hairless chest and Jack’s hairy upper body; Chris’ beautiful darker skin and Jack’s pale skin, which was rarely exposed to sunlight.

They watched the game intently, happy to be beside each other, nibbling on the snacks and making comments about the game and the pretty cheerleaders. The two-minute warning came and Chris began to unzip his jeans. Jack glanced over. “You are a horny fucker! We still have a couple of minutes!”

“I see that big lump in your jeans, Jack! What kind of visual entertainment do you have for us?” Chris asked as he wiggled out of his tight pants.

Jack smiled as he saw Chris’ sheer red bikini panties, with sexy dark red lace trim. He pulled down his jeans, exposing his sheer black bikini undies. “It looks like our warped minds think alike, Chris!”

Both men were semi-hard and almost fully naked. Jack cued up his video of choice, featuring one guy and two sexy professional team cheerleaders. In the opening scene, the two young hotties wander into the locker room, with the coach being the only other occupant. “Mmm, nice one already, Jack!” Chris gleefully said, as his right hand moved to his rapidly growing panty bulge.

Jack knew the movie well. He could not wait to see Chris’ reaction to what was to come. The coach’s double blowjob was enough to get some major rubbing in the red panties. Jack was being true to his name, stroking his panty-covered meat.

The blonde, frilly thong pulled aside, was riding coach’s huge cock when Chris reached for Jack’s. Chris spread his legs in anticipation of Jack’s hand. The brunette was licking dick, balls, and pussy, when she could reach it. Jack’s fingers rubbed Chris’ big bulge to reciprocate. “Holy shit! Nice boner man!” Jack complemented.

“Good one yourself!” Chris responded. He looked up at the TV. “God damn! Look at the one on her!” The brunette had her panties down, pushing her 9″ into the coach’s mouth.

Jack smiled. He knew Chris loved the trans action as he felt his dick thrusting upward. “Do you want to ’69’?”

“Hell yea!” Chris quickly answered, laying back down on the sofa. He made sure that he could get a occasional glimpse at the porn while dining on Jack’s ample cock.

Jack assumed the top position, immediately mouthing his partner’s meat through the sexy sheer material. Chris returned the favor, nibbling and licking Jack’s big bulge. Both men moaned in pleasure, panties stretched to the max. The uncut dick escaped the sheer black confines and slid into Chris’ waiting mouth. Jack released his friend’s nice shaft and tasted him, while fondling his bloated testicles.

“Oh God, yesss!” was the cry from the movie. Jack knew what was going on: The coach was fucking the blonde’s tight little ass, when the other cheerleader pushed her cock into his ass. Chris’ cock twitched and his bitter precum leaked into Jack’s mouth. He eagerly watched the video “fuck train” while stroking and intermittently licking his friend’s big cockhead.

Chris was getting close. Jack knew how much he was turned on and he backed off, perfectly edging his friend. The throbbing subsided while Chris recovered. “Damn, I almost blew my load!” he said as his meat was again covered with his pretty red bikini. He then went to work on Jack’s tasty rod. He had his big cockhead totally covered with his warm saliva.

It was a very sensuous to Jack. He worked the swollen Kurtköy Escort Bayan tip back and forth across Chris’ nice lips, feeling his tongue on the underside as he poked inside. Jack peeked up at the movie. Closeups of the two cocks anally pumping were making Jack more intrigued – and more turned on. He felt his cockhead throbbing inside Chris’ hot mouth. He needed to cum, but Chris took his cue from his panty mate, edging him so well before backing off. The see through black material snapped back across Jack’s big meat. Both men needed to be satisfied.

Jack dismounted Chris, getting on his knees. The movie ended with two anal cream pies as Chris stood before him. Jack went to work immediately, engulfing the throbbing bulge, panties included. Chris freed his meat, poking it out through one leg hole. Jack immediately began sucking on the head.

The movie was completed, but Chris kept thinking about all that cum dripping out of the well-fucked holes. He instinctively clutched the back of Jack’s head and pushed his lips to the base of his shaft. Jack’s eyes grew wide as he gagged a bit. However, he learned to accommodate Chris’ cock when he began thrusting rapidly. His red panties, still containing his smooth balls, were soaked with Jack’s mouth juices.

Chris was so close and there would be no denying his soon-to-be completion. Jack’s warm wet tongue and nice lips felt incredible – even better than how Anastasia could make him feel. The urge was strong.

Jack, now grabbing onto his mate’s ass cheeks, was letting him use his mouth. Of course, he had no choice. He felt the strong buttocks muscles clinching. The first blast was quite large, painting the back of Jack’s throat. It choked him. He coughed and jizz oozed out between lips and shaft.

The flood gates opened for Chris, but he was mercifully able to pull out a little. With lips clinched firmly halfway down his meat, his balls continued sending pulses of hot semen into Jack’s oral fuckhole. “Fuck, yessss!” he groaned as the final warm gush was completed.

Jack tried to keep his lips around his slowly softening shaft as Chris’ knees crumpled. It was futile. He fell back onto the couch, exhausted. Cum was everywhere: All over Chris’ dick and panties; on Jack’s lips, chin and chest; but mostly in Jack’s mouth. Proud of his oral work, Jack showed the pool of jizz in his mouth and greedily swallowed it all. He then proceeded to lick clean the well-sucked dick.

“God, that was heavenly!” Chris said, still high from his massive ejaculation.

“Damn, man, you must have been saving up for me!” Jack answered.

“Well, I a gonna return the favor, but in a ‘special’ way! I hope that you will be ‘up’ for it.” With that, Chris grabbed his overnight bag. “Point me to your bedroom, I will call you when I am ready.”

“It is the second door on the right, down the hallway. Mmm, I can’t wait long, so hurry!”

It took every bit of self restraint for Jack not to finish off inside his sheer panties. He took deep breaths to calm down, for the wait on his compadre was a long one. Finally, he heard a call from the bedroom.

“Goddamn, Chris, it took you long enough!”

“It’s ‘Christine’,” was the reply in a feminine voice.

“Holy shit! What the fuck?” was Jack’s response just before entering the open door. He stood there a few seconds, mouth agape.

“You like?”

“Hell yea!” Jack looked over his crossdresser sex mate with admiring eyes. “Christine” wore a long blonde wig, heels with ankle straps, fishnet stockings, black frilly sissy panties with open back, matching bra with silicone breast inserts, garter belt and a short black transparent gown. The makeup looked really good and she was definitely “passable”. Jack could not believe how sexy it all was to him.

“And I see that you are glad to see me!” was said with a sly grin, looking at Jack’s huge bulge. A tongue swirled across deep red lipstick. “It looks tasty to me!” Chris was in full character and would be Christine the rest of the evening. She pushed Jack onto the edge of the bed, working his big cock over the waistband of his panties. She immediately engulfed the swollen head. Taking him deeper, the red lipstick smeared all over his shaft.

Already lost in the roleplay, Jack moaned, “God, baby, that feels soooo good!” She looked up at his face, still teasing his bulbous cockhead with her sweet tongue. It was obvious that he was falling victim to the charms of Christine. Suddenly, his big boner plopped out of her slutty mouth. He got fully on the bed – the bed on which he had only one sex Escort Kurtköy partner, Beth. But now, that didn’t matter to him.

Christine followed, laying atop Jack. Her panties rubbed across his steely member as she lowered herself to his lips. Their tongues entangled almost immediately. She was no longer flaccid. Her bulge grew as Jack fondled her sexy stuffed bra. “Make me your whore, Jack!” she urged, while reaching to the night stand for the pink bottle of “Tush Cush”.

She rose from his body, applying the cold lube to his throbbing fuck rod. Jack did not resist, allowing Christine to take control. She hovered over his shiny shaft, back toward him. Jack had the perfect view as she began guiding his needy cockhead to her man pussy.

Jack’s cock made contact with her firm buttock cleavage as she guided it toward the ultimate destination. She looked hot in the sexy stockings and panties and he was growing even harder. He pushed his hips upward, touching her puckered rosebud.

Chris / Christine had never taken anything Jack’s size. The fuckdoll cock had felt really good, though, and she needed him inside her. Her heart was racing as she squatted more. Her entrance was being stretched, but was not painful, thanks to the quality lube. Finally she inhaled deeply, pushing downward more.

Jack could not believe how tight the sensation was. “Fuck yesss!” he groaned as his engorged cockhead slid into Christine’s forbidden hole. His heart was also beating rapidly, but he paused to allow his fuckmate to recover.

Christine was in heaven now, and so was Jack. She wanted all of his meat inside her. Slowly she took him deeper until his bloated balls nestled against her ass cheeks. She gazed back at Jack as he grabbed her backside and panties. She started riding his long thick shaft. He filled her back passage perfectly. “How does that feel, baby?” she asked. Meanwhile Jack was thrusting upward, pounding her prostate.

“Uh, uh, uhh. Goddamn fantastic!” Jack replied, panting and plunging faster.

“Bang my pussy! Fuck your whore!” Christine commanded as she leaned back on Jack.

He squeezed her fake tits, which were amazingly realistic and then slammed into her harder. After a few minutes they rolled over, getting into doggie position. When Jack resumed the hard fucking, Christine rubbed her own meat, through her frilly silken panties. “Breed me, baby!” she screamed, getting close to her own orgasm.

Sounds of flesh slapping against flesh and loud grunting filled the room. Jack grabbed Christine’s hips and drove his fuckstick in as far as it would go. His stiff balls begin twitching. She sensed his impending ejaculation and was frenetically working on doing the same.

“Oh baby, I am cummminnnng!” he yelled. Christine felt his cockhead dancing within her man cunt, delivering a blast of warm spunk into her inner depths. Three more spurts shot inside her. A bit oozed out as the pounding continued. Getting fucked in reality exceeded her expectations. The sensation of a real cock sperminating her ass was overwhelming. “I’m orgasming too, baby!” she moaned as her own juices spewed into her panty pouch.

Like a bull that just bred it’s mate, Jack collapsed against Christine, forcing her prone atop the bed. Both were quite exhausted, breathing heavily from the hot fucking.

The sizable dong was slowly shrinking inside the sissy fuckhole. The dam was giving way. Spunk began to ooze out, flowing toward Christine’s twice-emptied cojones. Jack’s semi-flaccid dick thrust in one more time and his thick cream gushed out. His large cockhead was the final plug: As it plopped out the boi pussy, another copious outflow of jizz followed.

Christine moved back to her hands and knees. Jack was amazed at how much seed she milked from him. He watched from behind as it continued draining out. Some dripped onto her sexy stockings. But, the main destination was the sissy panty pouch, where it combined with his fuckmate’s fluid.

Jack reached for her crotch, grabbing at her flaccid cock and balls. A squishy noise was made as he cupped her package. When he squeezed a bit, their spunk was forced through the panty material.

“I hate to waste all that!” he said, still in the mood for more. He flipped onto his back and worked his way to the cummy pouch. His wanton tongue eagerly lapped up all the exterior cream. After freeing dick and nuts, Christine was given a thorough licking.

Jack repositioned beside his lover. Their lips touched and tongues entwined until all the residual jizz was shared. “Holy fuck! That was the most intense fuck and cum ever!”

Remaining as “Christine” till the night’s end, she responded, “Baby, your love making was soooo good! I orgasmed really hard!”

The two slept together on the large bed for the few darkness hours that remained. They had one more day together and, undoubtedly, both dreamed of another steamy session.