She Begged Me to Help “Find Her Prostate” Because Her Husband Wouldn’t [F/M] [Anal] [Creampie]

I’m a massage therapist for wealthy people in a upscale part of Southern California. As a young straight guy, I can say my job definitely has its highs and lows. The highs are when I get to give oil massages to gorgeous, tan trophy wives.

The lows are when I have to give oil massages to their old, wrinkly husbands. (I’ll spare you my mental images of them.) Highs or lows, I’m a professional and I do a good job every time because that’s why they pay me the big bucks and the work is predictable.

At least … most of the time. Last week I had a *very* unexpected session with one of the trophy wives. We’ll call her Jamie.

Jamie is in her early thirties, and she is easily one of my most beautiful clients. Massage therapists see a lot of bodies, and I know who takes care of theirs. Let’s just say that Jamie’s gym routine has her in peak condition. She has curves in all the right places without any cosmetic surgery and she’s very toned with stunning muscle definition.

The other day I was in the middle of giving her a massage in one of her husband’s many giant houses. He’s a real estate tycoon who is rarely around. I may have seen him once in the dozens of times I’ve massaged Jamie.

She prefers massages in her exercise room, which has a bunch of exercise equipment and a balcony that overlooks a pristine beach that I am too poor to visit.

I had just closed the billowy curtains in front of the balcony and started rubbing oil over Jamie’s shoulders and back when out of the blue, she asked me “Do any of your female clients have you massage their prostate?” Now, some clients enjoy chatting during their massages but this was *definitely* the first time I’d heard that question.

I didn’t want to piss off one of my most valuable clients, so I chose my words carefully. “Hm, I can’t say they do. I know muscles a lot better than internal organs, but I think I remember from anatomy class that only men have prostates.”

She had been lying face down on my massage table, and she pushed herself up on her shoulders and looked at me with a skeptical look in her eye. “No, I’m pretty sure we have them too.” I wasn’t about to argue with her or sound like I’m trying to mansplain female anatomy. I was caught a little off guard at this naïve comment though … Jamie was not only the hottest but she was also the most educated. “You’re probably right! Like I said, I know muscles.”

She laid her ample breasts back down on the table and I kept working. There were a few minutes of an awkward silence before she piped back up again. “I think I’d really like you to help find my prostate today. I am willing to pay you extra. Of course, if you really don’t want to, I don’t want to make you uncomfortable. You do a good job and I don’t want to scare you off.”

“Uh, Mrs. Scott, I think that’s something … that um … husbands normally help with,” I said nervously. This wasn’t the answer she wanted. “Frank is a smart, successful man, but he’s not helpful with this sort of thing. I’ve helped him find his prostate many times, but every time I ask him to find mine, he says that’s gross. He says there are only two holes of mine that he’s interested in, and there isn’t a prostate in either of them.”

I was shocked for more than one reason. First, that we were even having this conversation. Second, that her husband was such a selfish lover. Third because it looked like I would be massaging a part of Jamie that I’d never touched before.

“I … I would be willing to do that if you really want that,” I said finally. She seemed genuinely excited and she flung the towel that had been covering her ass onto the floor. “Thank you so much! I’ve tried myself but it must be *way* in there.” I still couldn’t be sure if she was serious.

I squeezed some massage oil at the base of her back and watched it run down between her perky cheeks. I’d obviously massaged her ass before because she does so many leg exercises, but this was the first time I’d be going … in between.

I slowly ran my thumb down the trail of oil until I felt her asshole. I started rubbing back and forth gently. At this point, Jamie reached back and spread her ass, a movement that also spread her pussy lips a little. It could have just been excess massage oil, but I think a little bit of cum leaked out onto the table.

“Go slow,” she said quietly. “I’m tight.” As a massage therapist, I am pretty much an expert at not getting turned on while touching a client at this point, but this instantly made me hard.

I massaged her asshole with my thumb for a few minutes until I felt her loosening up to my touch. “Are you ready, Mrs. Scott?” She nodded. I pushed my index finger into her asshole and Jamie inhaled sharply. Her hole closed tightly around my second knuckle. It was warm. Almost inviting. I worked my finger in and out, feeling her insides.

“Mrs. Scott, I don’t feel your prostate,” I said after a few minutes. Maybe … maybe you can use a toy to find it later. I think that’s what a lot of women would do in this situation.” She gave a defeated sigh. “Frank doesn’t let me have toys because he says they’ll make me loose and unfuckable.” Frank sounded like a grade-A asshole.

“If you want to, you could look for it with something … longer than your finger,” she said trying to sound innocent. My cock became rock hard and I was worried she’d see it. I looked up, and she was already staring at the cum stain forming on the front of my pants. She was smiling. I smiled back and eagerly nodded.

Jamie stood up and got off my massage table. She walked across the room toward her balcony and gripped the curtains with both hands. Then she bent over. “It’s got to be in there,” she mumbled just loud enough for me to hear. Her silhouette was breathtaking.

I walked over behind her and unzipped my pants. I drizzled a little of my massage oil on my dick and started rubbing my shaft between her supple ass. “I’ll guide you in,” she whispered. I expected her to work up to actually doing this, but she reached back, firmly grasped my cock, and shoved it deep into her asshole.

I felt all the muscles I had just massaged tense back up. I was undoing my work, and it felt incredible. I started thrusting and she gripped the curtains even tighter. She was pushing back against me to make sure the rim of her ass gripped every ridge of my cock and touched the base of my dick.

“I … don’t … feel it,” I said between gasps. She was moaning quietly at this point, and I was worried a gardener or someone would hear us outside her window. “K-keep looking,” she whimpered.

I fucked Jamie’s ass until I felt her knees start shaking. I could tell she was on the verge of an orgasm from the way her asshole was quivering. I surprised her by pulling out immediately after a thrust and then shoving my entire cock back into her hole. That did it. She gasped and tried to stifle a loud moan. Cum was running down her legs from her pink, wet pussy.

I couldn’t wait any longer. I reached around and grasped her large tits and came inside her. Her nipples were rock hard as she felt my warm cream splash around inside her. Now it was *my* legs that felt weak. I leaned forward and she supported my weight so we didn’t stumble out onto the balcony. Her hands held mine on her firm breasts as we both tried to catch our breath.

I slowly pulled out. Her puckered asshole was tight around the head of my dick for a few seconds. “Fine,” she said with a giggle. “I guess I’ll let you go.” Her hole loosened just enough for my cum-covered cock to slide out, and then her hole closed back up tightly.

Jamie turned around and smiled at me before walking back over to the massage table. She was moving slowly, as if I had massaged part of her that hadn’t been touched before and she was now sore. She picked up the towel, laid down, and covered her ass.

“It’s a shame you couldn’t find my prostate,” she said with a hint of fake regret in her voice. We’ll have to use a toy next time like you suggested.”

*Next time? I get another try*? “That … sounds like a great idea,” I said.

I shoved my cum-covered dick back into my khakis and walked back over to the table. I started massaging her shoulders like nothing had even happened. But something had happened, and the little streams of cum that were leaking out of Jamie’s holes onto my massage table were the proof.

Source: reddit.com/r/sexystories/comments/p6baxe/she_begged_me_to_help_find_her_prostate_because