Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 5 by jk89 jk89

What's next?

Time to fuck your boss's wife

Happy to oblige, you quickly stripped off your shirt and tossed it aside, while simultaneously kicking off your shoes. Mrs. Jensen stared at you with hungry eyes, licking her lips when she saw your chiseled physique then brought her attention down to your crotch, anxious to see just how big you were. It didn't take long for her to find out, as your pants and boxers were pulled down together in one swift motion, finally freeing your hungry trouser snake from it's confines.

"Ohhh fuck, look at that big, beautiful dick you've been hiding! It's sooo long and thick! Put it in me David. I need you to fill me up!" she pleaded, lying back with her legs spread wide.

You didn't need any more encouragement than that and had moved to stand directly in front of her, grabbed hold of one of her legs, lifting it up in the air, then lined your throbbing member up with her opening. With her pussy fully primed from your oral attention, it only took the slightest nudge of your hips for your bulbous head to penetrate her, causing Mrs. Jensen to let out a gutteral moan.

Please log in to view the image

You've always loved experiencing a new woman and the feeling of sliding into her pussy for the first time, and this situation was no different. Mrs. Jensen's wet, velvety folds enveloped you without any resistance, sucking you deep into the hot, steamy cocoon of her sex, quickly accommodating to your size, and allowing you to begin thrusting in and out of her nearly immediately.

Mrs. Jensen was happy to let you take control, moaning out in delight and becoming more and more vocal as you worked your length in and out of her dripping gash. "Oh fuck yeah, that's what I needed! Make me take every inch of your big, fucking, young cock! I'll take it all fuckin' day. Oh god-fucking-damnit!!" she screamed out as you began moving faster, bumping into her cervix with the head of your dick with each plunge inside.

As you had settled into a rhythm you knew you'd be able to maintain for a bit, you began thinking about how you'd started to really enjoy fucking all of these more mature women you'd met through work. You'd found in the past that some of the girls you'd been with, sometimes had trouble handling your size and you had to shorten your strokes or go at a much slower pace than what you'd prefer. Sure, there's something about being able to see the look on a tight, little 18-year old's face when they realize you're going to stretch their pussy out it ways they'd never experienced before, but there's also something about a woman like Mrs. Jensen, taking every inch of your dick and loving it, while talking like she's some cock-hungry, dirty whore. She wasn't alone, either. It seemed like the vast majority of the massage clients you'd fucked had been more vocal, weren't afraid to tell you what they wanted, could handle your dick without grimacing, and had also been more willing to do more risque things. Just as you had finished that thought, Mrs Jensen's dirty talk caught your attention once again.

"Oh fuck David, do you feel how wet my pussy is for you? You're getting me so close! Keep fucking that little pussy! Make me cum again!" she begged as her hand moved between her legs and began frantically rubbing her clit.

Please log in to view the image

"Shit, don't stop! Keep going!... Ungh, keep goooiiiiinnnng!... Uuunnnnggghhhhh!" she yelled out as her body began shaking beneath you and her pussy contracted around your dick, releasing more of her cum onto you, and causing wet, squishing noises to be made every time your hips met her's.

Watching her orgasm beneath you and feeling her juices coating you had turned you on even more and you had picked up your pace, bottoming out on her with each thrust and banging into her cervix and making Mrs. Jensen squeal in delight.

The only problem with the faster pace was that you soon felt the cum boiling up in your balls, and you knew you wouldn't last much longer if you didn't change things up. As was usually the case when you were fucking someone, you were torn with what you wanted to do. A huge part of you wanted to cum right then to enjoy the incredible release of pressure that was steadily building within your loins, but another part wanted to make this last as long as possible and make Mrs. Jensen cum a few more times. What you decided, was to give her a warning that you were close and let Mrs. Jensen be the one to decide if she was ready for your session to conclude.

"Oh fuck Mrs. Jensen! I'm getting close! I'm not gonna last much longer!" you warned her, clenching your body tight, trying to coax a few more seconds worth of fucking out of your, ready to burst, dick.

"I want to see it David! I want to feel your hot load all over me!" she had eagerly told you as she propped herself back up on an elbow.

That was all you needed to hear, and no longer trying to hold back, you thrust your pelvis into her pulsating cunt, spearing your cockmeat into her again and again. After what couldn't have been any more than thirty seconds, your balls began to tighten and you felt the sensation of your boiling cum traveling up the length of your shaft. Quickly withdrawing, you reached for your dick but Mrs. Jensen beat you to it. Taking hold of you with an overhand grip, she immediately began stroking your cock.

"Oh Fuuuucccckkkk..." you had groaned out as she clenched your member tight, rapidly tugging on your shaft as she looked at you with a devilish grin on her face.

"C'mon, bust your fuckin' nut all over me. Make me your dirty, cum-soaked whore!" she told you, obviously excited by the idea. "Make those nuts burst all over my belly! I want it! I want you to cover me with that big, salty load!"

If you weren't so close already, that dirty talk would have definitely pushed you over the edge and in the next second, the first of your blasts erupted from your bulbous cockhead and landed just below her ribcage.

Mrs. Jensen called out encouragement as she continued wildly jacking your cock, pumping thick white streamers of your cum all over her stomach, hips, and inner thigh. "Yeah baby! Shoot your hot load all over my belly! Cover me with all that nasty, dirty cock juice! Make me your little cum slut!"

Please log in to view the image

Eventually, your spurts began to slow to a dribble and when Mrs. Jensen was confident she had milked the last of the cum from your balls, she released her grip and began playing with the sticky substance that now painted her body, smearing it around her stomach and rubbing it into her freshly fucked pussy.

Feeling ready to collapse from exhaustion, you stumbled away from her and leaned against a nearby wall, while you caught your breath, tried to steady your legs beneath you, and come back to your senses. After several moments passed, you happened to glance up and saw Mrs. Jensen was now staring at you, to which you responded with a lopsided grin.

"So what do you think David, are we going to make this a regular thing?" she asked at that point, batting her eyelashes at you.

It didn't take you long at all to accept her proposal and the two of you came to the agreement that her booking a massage with you every other week shouldn't raise any suspicions. Following that, she invited you to join her in the shower to rinse off, where the two of you spent a fair amount of time washing, groping, and exploring each other's bodies a little more. Just when it seemed like the two of you were going to go for a second round, Mrs. Jensen put a stop to it, telling you that as much as she'd love to fuck you again, it was probably better for you to get going.

Agreeing that she was probably right, you had stepped out of the shower, toweled yourself off, then slipped back into your clothes. You next returned to the room where you fucked, packed up all of your massage equipment, and folded up the table while Mrs. Jensen stood nearby watching you, wearing a sexy, silky, blue negligee with thin, spaghetti straps that only fell to the top of her thighs.

Please log in to view the image

As you had moved to leave Mrs. Jensen stopped you and slipped an extra $200 into your hand. "I wouldn't think of letting my massage therapist leave without a tip." she had said smiling, then dropped her voice to a volume slightly above a whisper, saying in a conspiratorial tone, "It makes my pussy tingle even more to think I'm using my husband's money to pay you to fuck me. I can't wait to see you again in two weeks." she had told you before kissing you on the cheek then walking you to the door.

What's next?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)