Sensations

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Bob rocked on it, feeling pleasure in spite of himself. How could he have been so stupid! Tiffany was one of the cross-dressed performers! He remembered her now, although she had been dressed very differently when they had watched the show, & wore a different wig, too!

Steph pulled back, her excitement climbing to ever higher heights. He, too, of course, was getting ever more excited as he was following her lead as usual. He seemed to love that cock in his ass. It was a little longer than the strap on Steph had used on him, but thinner, he thought.

Steph sat back in the chair, & began playing with herself as she watched Bob get fucked by the pre-op transexual. Bob was watching Tiffany's breasts sway as she hammered her cock into his asshole. This felt great! Bob wrapped his legs around the slim she-male's waist and thrilled to Steph's open masturbation. When Steph came, Bob spewed his cum over his belly. Tiffany cranked up her fucking of his ass until she came inside the condom, then dipped her head down & started licking Bob's cum off his body. He grunted unhappily when her cock slipped out of his ass.

"Aw, poor baby wants more cock, Steph," Tiffany teased.

Steph rose & started putting on her strap on, attaching a larger cock than the one she'd used on Bob previously. Bob felt her slip the plug end into her cunt, & groaned in pleasure. After she'd adjusted the straps, she stepped between Bob's thighs, & pushed the monstrous thing deep into Bob's bowels.

Bob was getting fucked again. Tiffany was removing her condom, & climbing onto the table. She placed her cock within easy reach of Bob's panting mouth & told him to lick her.

Bob's eyes went to Steph, then to the glistening, cum-covered limp cock in his face. He could feel Steph's excitement as the thought of him sucking cock transferred itself to his psyche, and although his mouth was dry from breathing so hard for so long with his lips open, Bob licked it. He tasted the "girl's" cum on his tongue, & it disgusted him, yet Steph's feelings soon took over, & he found himself sucking it in, laving it with his tongue as his mouth began to water. His head was bobbing up & down, & his neck was getting very tired. Finally, Tiffany straddled his head & fed her cock to him while Stephanie pounded that larger dildo in his slippery ass. Her excitement was really getting to Bob as he sucked on the shemale's dick, & soon he felt it start to expand in his mouth.

They were all thrilling to their little orgy, when Bob gasped at the table creaking under him. Steph stopped pounding his ass, & Tiffany slowly climbed fown off of the table.

Steph laughed. "Guess it's getting to be too much for my table to take. Time to move this party to the bedroom."

Bob whined when Stephanie's cock slipped out of him before he even realized it. The girls laughed at that, promising a lot more anal pleasure for him as they led him into the bedroom on shaking legs. Tiffany popped a Viagra while Steph removed her strap on. They put Bob on his knees, with his face between Steph's legs, as Tiffany crawled up behind him & began to fuck him again. He'd seen her long cock by now, & noted that it was both longer and thicker than the first phallus Steph had used on him. He guessed that the butt plug had loosened him up until it seemed thinner to him, as Tiffany slid her solid eight inches of meat into his distended anal portal. Bob grunted with pleasure & started licking at Steph's pussy, & soon they were all cumming again, while the cocks of Tiffany & Bob remained hard from the little blue pills.

Before the night was over, Bob had sucked both of them off, he'd been fucked three or four times by each of them, & once he fucked Steph while Tiffany plowed his loose asshole. He also got to fuck Tiffany, while Steph fucked his ass some more. He & Tiffany weren't even shooting cum any longer, just dribbling a little clear fluid when they came. Steph got to watch Bob fuck Tiff, & when Tiff wanted a break she fucked Bob while the sexy t-girl watched. Eventually, Bob fell asleep again, with Stephanie's dildo buried deep in his ass. She nodded off as well. They stayed locked together as Tiffany rolled out to the couch & finally passed out, herself.

Hours later, they drove Tiffany home, with Bob's ass plugged up with an even larger butt plug.

As Tiffany waved & walked up the stairs to her apartment, Steph turned to Bob & said "I don't know about you, but I had a lot of fun! I had so much fun that my pussy hurts!"

Bob agreed that he was sore as well, & they both laughed as they drove off to get some breakfast. The next day was spent with Bob in the nude, doing all the cooking for Steph, since he was her "slave" for the moment. Neither of them thought a whole lot about sexual activity, since they'd pretty well worn themselves out with the hot t-girl. Bob was still enjoying the sensations of having breasts. & Steph often had him pose for her, just to keep an edge to their play. He/she seemed to like it best when he had to pull his cheeks apart & bend over for her to plug him with an even larger anal toy. That night, as they went to bed, Steph played the last DVD for them both. There was a lot of man-on-man action going on, & Bob found himself getting aroused by it, in spite of his sexual exhaustion. He'd quit thinking about his own reactions to things, & simply immersed himself in Stephanie's sensations.

By Tuesday, they were ready for more sex...well...Steph was certainly ready, & her feelings went into Bob, who may have not usually been so eager for more, just yet.

Unknown to Bob, Steph had found the red haired man's number, & she called him that day while Bob was taking his shower. Bob knew something was going on. He felt the phone in her hand, & Steph's excitement, but he knew no specifics.

Steph started teasing Bob by putting on her strap on as he watched through the open doorway, which got to him much more than she might have thought, & when he came out of the bathroom, he already was erect for her.

"Bend over. Bob. Let me see what you have for me."

He immediately bent over and opened himself up for her. She teased his little bud for awhile, then slid it in a bit, letting him think she was going to do him dry.

Bob tensed up & pulled away from her. Steph laughed & said "What? You don't want a nice deep dry fuck, Bob?" She thrilled to his wide-eyed look of fear, & backed off & removed her toy attachment.

"Let's watch that movie & enjoy some wine before we get started," she suggested playfully.

She put the movie back on where the man was surprized by the big-cocked black body-builder. Steph loved the way Bob seemed to get excited at the same spots that she did, as was evidenced by his rising cock & flushed skin.

"C'mere, Bob," she cooed, lying back & spreading her legs for him.

Bob crawled on top of her, & easily pushed his cock into her slippery pussy. He felt like he was fucking himself as he grabbed her tits & flicked his thumbs over the nipples.

Meanwhile, the red-haired man. whose name was Jerry, let himself into Stephanie's front door. He immediately stripped off his clothes, & walked to the bedroom. Steph saw him, & told Bob to close his eyes & imagine the best thing he ever thought of, sexually. She said she would try to guess what it was.

He was cooperative, but apprehensive. He could feel that something was up, but had no idea what it might be. He kept fucking her, and her legs wrapped around him, then moved on down to lock behind his knees. She spread him open for Jerry, who stood at the door, watching them. Jerry grabbed the handy bottle of lube, & greased up his cock as he walked silently over the carpeted floor to the bed. He reached down & slapped a glob of lube on Bob's ass as Bob jumped & lurched within Stephanie's clasping pussy. Bob looked over his shoulder at the man who'd kissed him at the bar just a few nights before. He looked at the cock that Jerry was slowly jacking, & saw that there were a good 11 inches of cock there for him. Steph's excitement overrode his apprehension almost immediately, & Bob found himself raising his ass up for the inevitable invasion of Jerry's super-sized organ.

Jerry got on the bed, aimed, & entered Bob very quickly. Bob was amazed at how easily that pole of his went into Bob's bowels with no pain at all. Evidently, Steph's constant use of butt plugs & strap ons had done their job well. Bob felt only pleasurable pressure as Jerry picked up the pace & began fucking Bob into Steph.

Steph was in heaven. She had Bob getting his ass fucked by a huge cock, all while he was fucking her. Ever since she'd seen that scene in the movie, she knew that that's how she was going to introduce Bob to man cock. She just knew it would work, & was thrilled that he had gone along for the wild ride. Now, however, she didn't want to cum just yet. She wanted to watch Bob get it from a guy. She asked Bob to raise up a bit, & when he did, she rolled out from under him, & sat in a chair by the bed.

"Fuck him good, Jerry. He really likes your big cock. Don't you, honey?"

Bob was nonplussed. Yes, he enjoyed the sensation of having that big warm cock in his asshole. Yes, Stephanie's excitement was still in control, but he had felt nothing but revulsion at the thought of men for his entire life. Yet here he was, on his hands & knees, taking it in the ass while his favorite piece of ass watched him getting plowed by a much larger cock than his own. Steph began to stroke her pussy, & before he could really think about all of this, he fell back into the maelstrom of swirling images & sensations that it caused in him. Her actions caused him to cum with her long before Jerry spewed his fluids into Bob's belly. He came & came again as the big man fucked him harder than he'd ever thought he could take.

Bob found himself screaming "Fuck me! Keep fucking me you big fucker!"

Jerry complied, having taken Viagra a couple hours before. Bob got the ride of his life from this huge man, & Jerry was loving the way he could take it. Most of the guys Jerry fucked had eyes that were bigger than their holes, & started begging him to stop long before this. He gripped Bob's hips, & spun them both so that Bob was on top, grinding his bottom down onto Jerry's big prick.

Bob was in a frenzy. His legs forced him up & down on that massive pole, seemingly of their own accord. He glanced over to see Steph frantically rubbing her clit as she squirted her cum from her spasming pussy. Bob howled, & shot his load over Jerry's hairy chest. Steph kept cumming, & Bob followed suit, his hands grasping painfully into Jerry's pecs as his ass bounced up & down. Jerry, in spite of the Viagra, was only human, after all, & Bob felt his cock get even bigger as it pulsed its seed into Bob's clamping asshole. His cock, however, stayed hard from the medication. So, after a few second's rest time, Jerry started pumping into Bob again.

Bob looked over to Steph as she brought them both to yet another orgasm, & made his decision. What he did now, he was doing only for Stephanie. He leaned down & kissed Jerry right on the mouth. Jerry was still fucking Bob's ass. Bob was still on the ride of his life. Steph came so hard that Bob feared he'd pass out again. He moaned loudly into Jerry's mouth as his cock spewed the last of his balls' contents over the big man.

Bob laid on the huge hairy chest, his breath coming in gasps as Jerry continued his anal onslaught. Jerry rolled him over again, threw his legs over Jerry's shoulders & plowed his poor abused hole for yet another twenty minutes before collapsing onto Bob. Then, without a word, Jerry pulled out his cock & walked out, dressed & left.

Bob lay there, cum leaking from his gaping ass. He laid with one knee up, so Steph could see what the assault had caused in Bob's ass. She was looking at him wide-eyed, unsure if he was going to be mad at what she'd done. Bob felt her fears, & erased them with a laugh.

"Wow! Now that sure was something I won't be telling my grandkids about!"

Steph burst into happy tears as she guffawed & jumped onto the bed to hug him tightly.

"Thank you for that, Bob!"

Bob mused on the fact that he still had a week & a half of his "enslavement" to Stephanie to endure. He wasn't really convinced that he'd survive it, but he sure was willing to try.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 14 years ago
&&&&&&&& ???

What's with all the ampersands? Give me an "a"! Give me an "n"! Give me a "d"! Was that so hard? Actually using the word "and" would make this highly interesting story very much more readable.

Share this Story

Similar Stories

My Wife, Transformed A couple gets an opportunity for some role reversal.in Transgender & Crossdressers
Be Careful What You Wish For Larissa sells her soul and gets more than she bargained for.in Transgender & Crossdressers
The Transformation Device Ch. 01 Dr. Sanderson creates the ultimate Device for people's needs.in Transgender & Crossdressers
Nymphomania Ch. 1 College guy is kidnapped and transformed.in Transgender & Crossdressers
The Escape Room - Room 01: Sammy An elaborate escape room turns four women into bimbo sextoys.in Mind Control
More Stories