Disable your Ad Blocker! Thanks :)
Chapter 5
by mattpantyhose
meeting the first guy
Things get complicated
"John, darling" Jesse sweetly began "I'm so glad that you agreed to have sex with another man for me. I found a perfect candicate, but there are few perks to that deal. He says he isn't gay, but he'll gladly fuck a submissive girly-boy. He wants me to lock you in chastity and feminize you a little."
"What?!" you were confused.
"Nothing serious. We'll just shave your body and get you into sexy lingerie. And that chastity will be just for that night. I'm sure it's nothing you couldn't handle, right? Remember about the reward..."
"Well... I guess I could do that, if it pleases you."
"Oh yes! I'd love that. Thank you! You're such a sweetheart."
She leaped onto you and kissed you passionately, fervent make-out session followed, but it did not end up in sex, even though you got hard already. Instead Jesse stepped back and said:
"Let's get started. We got a date tomorrow and I need you to be ready."
It turned out that Jesse was a better organiser that you had know, she had already bought the extra shaving foam, razors and even a set of sexy red lingerie consisting of lacy panties, matching bra, sheer black stockings and suspenders; she went as far as to buy a pair of fuck-me-pumps on thirteen centimetre tall stiletto heels. You spent half of the evening in the bathroom getting your body hairless and smooth, then after a joint shower she dressed you in the sexy lingerie and you made out again. Still no sex though, Jesse teased you mercilessly, but did not allow you to climax.
"I need to get you in a proper mood" she explained in a playful voice.
After the teasing she used ice cubes to get your cock soft again and then she locked it in the chastity. That was not the end of feminization though, Jesse had prepared also a make-up and a wig and she diligently applied it all to your face and head.
You spent next two hours interchangeably practicing to walk in your new high heels (which fit surprisingly well) and making out with Jesse. Your cock was desperately trying to get hard in its cage, it was uncomfortable but made you even hornier.
Eventually your date arrived and to your astonishment it was your roommate David!
"Hi Jesse!" he groped her buttock as he said that "woah! You've told me that you'll doll up your faggot boyfriend, but you never memtioned that he could be such a sexy girl. Ready to suck a real cock, slut?"
He adressed the question at you, but you just stood there frozen. When you agreed to suck another man's cock to please Jesse you never imagined it would go that far, but as the event proceeded you just rolled with them. Now you were standing in your room, your entire body smooth shaven, dressed in nothing but sexy lingerie, with a slutty make-up on your face and a blond wig on your head. Your cock was locked in a chastity cage and despite the dreadful predicament still was trying to get hard. Why was all that turning you on?!
"Come on, bitch!" David hurried you "let's not waste time. Get over here and suck my cock."
You still did not move, you simply could not. Your roommate reached you in few quick strides, pulled you towards the bed and pushed you onto it. You landed with your knees on the ground and your ass sticking up on the edge of the furniture.
"I see that you need more incentive. I'll show you" having said that David slapped your buttock hard with his large palm.
More slaps followed soon after, they were not all that painful, but loud and the sense of humiliation was overwhelming. After few strokes David stopped, turned you around and pulled you down to your knees.
You were kneeling on the floor with his crotch right by your face.
"Pull out my cock, slut!" he commanded and for the first time you acted.
You unzipped his trousers and hesitantly pulled out his cock. It was huge! That monster was something that could belong to a pornstar, but not an ordniary man. Would it even fit into a regular pussy? What was even worse were the testicles hanging beneath it, they were proportionally thick and must have produced insane amounts of cum.
"Suck it, bitch!" came another command and this time you hesitated a little longer.
"Please, baby, do it for me" Jesse reminded the both of you that she was still there. She also reminded you WHY it was all happening "it's all turning me on SOOO MUCH already! I need to see you suck on that amazing cock. Please! I'm sure you'll love it too."
David was smart enough to remain silent this time and it helped, you overcame your hesitation and finally put your lips to his fat cock. Your own penis never ceased to stop trying to get hard in its cage, you were amazed by the realization that this entire activity was indeed turning you on.
You have never sucked a cock before, but as a man you knew what you enjoyed to receive yourself and tried to perform just that on David's cock; its size was the limiting factor, though. You would have never thought that the Julia Roberts mouth and Angelina Jolie lips that you had and for which you had been mocked in high school could eventually be of any use, but this was the day.
You began by licking the head then proceeding to the incredibly long and thick shaft, but that could only last so long. Eventually you opened your mouth wide and took the monster in, first just beyond your lips, but soon it proceeded further. There was obviously no way you could deepthroat that massive cock, but you tried to swallow as much of it as possible.
At some point Jesse came to you and knelt by your side, she did not interrupt, but just observed from up close.
"I love you, baby" she whispered into your ear "you're amazing, this is so hot."
She took off her shirt and bra and began to play with her large breasts.
"Mhmm yeah...." David had to speak up again "you're really good at that, slut. You must've sucked numerous cocks before. If you keep it up you'll make me cum."
Fulfilling that promise turned out to be a lot more time consuming that you would have thought. David definitely did not suffer from premature ejaculations and had a truly impressive stamina. It took a lot of effort, sucking, licking and stroking to bring him to an orgasm.
"OH FUCK! I'm cumming!" David roar sounded almost like a relief to your aching jaw.
He grabbed your head. but did not push his cock deep, only its head remained beyond your lips, then he started shooting. You would have never imagined that a man could cum so much! It was an endless steak of semen shooting into your mouth, you had **** but to swallow, but even then it was too much and too quickly for you to succeed.
At some point he pulled his still ejaculating penis out and aimed it at Jesse's breasts, he had enough seed in his balls to cover them as well. When he eventually finished he said:
"What are you waiting for, bitch? Clean her up! This entire load is for you."
Before you moved he slapped your face few times with his still hard cock. After the long cocksucking you were feeling too submissive to object, so you leaned towards Jesse's breasts and began to lick them clean. Soon every drop went into your throat and clearly satisfied David exlaimed:
"You did a good job, slut. We'll definitely have to do it more often" with that he left.
When he closed the door behind he Jesse spoke:
"That was amazing! You're the best, honey! Thank you, I love you so much!"
Then she kissed you, despite your aching jaw you put as much effort into the long passionate kiss as possible. You were insanely horny and making out with your gorgeous girlfriend was just the thing you needed, at least the first step.
Would that, indeed, be just the first of many times? Would that chastity remain on your cock? How often would you wear the sexy lingerie?
What's next?
To Cuck or Be Cucked
It's up to you.
You. Your Girlfriend. Two Horny Roommates. And Their Girlfriends. It can go whichever way you choose.
- Tags
- Stripper, Lapdance, Cheating, Bachelor Party, Strippers, Blowjob, Creampie, Cuckold, Cuckquean, domination, swallowing, submissive, facial, bitch, alpha, bareback, cum, stud, cowgirl, woman in control, Fuck, Dirty talk, Rimjob, Rimming, Swallow, Facefuck, Teasing, Dominant, Scheming, Cleanup, Clean up, Semen, CEI, Cuck, Hotwife, Angst, Girlfriend, Bull, Cock, impreg, impregnation, insemination, cuckcake, finger fucking, good girl, whore, dominatrix, mistress, lesbians, cum eating, facesitting, deepthroat, ownership, sleeping, Bisexual, Cock sucking, Office, Sissy, feminization, chastity, humiliation
Updated on Feb 25, 2025
by MissMuse23
Created on Oct 30, 2018
by rc206
You can customize this story. Simply enter the following details about the main characters.
- 7,024 Likes
- 2,227,017 Views
- 1,874 Favorites
- 1,211 Bookmarks
- 128 Chapters
- 14 Chapters Deep
- All Comments
- Chapter Comments