From co-worker to sex worker [MF]

I really enjoy this sub and thank authors for sharing. I though I might share one from last year as my first post.

Lisa (29) was a friend of my younger brother. I had known her casually for many years, Facebook friends that kind of shit.

We chatted occasionally, a little flirty but nothing overt. She was looking for a new job, and I got her an interview and gave her a recommendation for a administrative position at a large company I work for. (I’m a manager for a different department than the role was in).

Through her own merit she got the job, all I did was open then door.

When I was at the workplace where she was based, I’d regularly take her for lunch, and these conversations often took a intimate turn. She would discuss her tinder dates and how they went, whether they sucked or whether she ended up sucking.

Lisa asked about my marriage, and I (43) was honest that my 20 year marriage was now very close to being sexless.
“So how do you get by?” She asked

“I abuse myself regularly.” I replied laughing

“Surely you need more than your hand though”

“Well, I also see a professional occasionally” I said cautiously.

Lisa probed for details and eventually I relented and told her about Olivia, a massage therapist that provides some other specialised services as well that I have seen a few times a year for the last couple of years.

“You mean you get a happy ending?” Lisa asked

“Well, I guess, but it’s more than a rub n tug, she provides touch and intimacy and has very skilled hands in a number of ways”

Our lunch ended and we returned to work. The following week we went for lunch again and despite my efforts to change the subject Lisa persisted in getting more details about my massage service.

“So you pay for someone to get you off?”
I got a little defensive again explaining that it was more than that.

“So how much do you pay for this ‘massage’?” Lisa asked.
I refused to answer and again our lunch ended.

Next lunch Lisa was quieter than usual, eventually she said “what about me?”

“What do you mean what about you”

“Would you be interested in some business with me?”
I was surprised but wanted her to be clear about what she was asking as she was a co-worker.

I asked her to explain more.

Lisa started talking faster now, saying how she had been thinking about my paying for intimacy since last week and it was interesting to her and even turned her on a bit.

“Would you be interested in paying me to spend time with you?” She eventually asked.

“It depends” I stated

“On what?”

“Well, if you’ve clearly thought this through, if you really want to do this, on what you’re willing to do and how much you want for it?”

I continued, “I want to be clear that this would be a transactional relationship. I’m not looking for an emotional one.”

Lisa indicated that she understood. I told her to think about it some more and we’d talk again.

My phone buzzed with a snap from Lisa the next day.
“I fucked myself last night” was the message that accompanied a snap of her biting her lip”

“Tell me” I responded.

“I thought about fucking you for money” was the next snap. The office clearly in the background of her snap.

The messages went back and forth, and I decided to go with it. We agreed on an hourly rate and a time.

I booked a local motel for a couple of days later.
“I’m going to need a drink when I get there, I’m nervous but excited” Lisa messaged.

I left work a little early and checked in after buying a few pre-mix drinks. I let Lisa know the room number and awaited her arrival, taking a shower. I was already hard thinking about the taboo nature of what was about to happen.

Eventually there was a light knock at the door, and I let Lisa in with a hug. I was wearing a towel only.

Lisa was in her work clothes. Lisa is short, blonde and a little curvy. With massive G-H cup breasts that always were a feature of whatever she wore. Pretty hard to hide those puppies!

She sat down on the edge of the bed. I handed her an envelope with our agreed fee. Lisa grabbed a drink and drank quickly. I could tell she was nervous. I told her that is was perfectly fine to walk away from our deal at any point. She finished her drink then reached over and slid her hand under her towel.
“I’m good” she said, looking me in the eye as her hand found my growing cock.

“I want to see you” I told her.

She stood then. Removing her top showing her large soft breasts in a beautiful soft green bra. She turned away from me and undid the slacks she was wearing and slid them down revealing matching undies.

“Are you still okay?” I asked.

Lisa again responded with actions instead of words? Turning around, grabbing my hand and guiding me to her pussy. I felt the warmth before I ever felt the wetness that coated her outer lips.

I played there for a while as she pushed against my hand. I explored her, coating my fingers with her wetness.

Standing up I slid my hand up to her mouth, she took them into her mouth, sucking on them, cleaning them.

I used my other hand to gently push down on her shoulder, Lisa understood and kissed her way down my stomach, used her teeth to unwrap the towel and took me into her warm mouth. She slid my cock all the into her mouth, my cock disappearing completely. She held her mouth there, she looked up at me, as she then slowly began to deliver a very very good blow job. Her hand teasing my balls, her spit dripping from the tip of my hard cock when she let my cock pop out from her lips.

Before I got completely carried away I stood Lisa up, slowly removed the remaining underwear and then had her lie face down on the bed. Reaching for the massage oil I had brought with me, I drizzled it over her thighs, ass and back. She twitched as the cool liquid hit her soft pale skin.

I worked my hands up her thighs, massaging slowly and deeply. Despite her opening her thighs, I ignored the warm area between them, massaging her ass, sliding my thumb gently over her little asshole.

She pushed back a little, but I continued the tease. I straddled her legs and massaged the oil into her back. As I stretched forward my cock slid up between her ass cheeks. I maintained this motion for a short time, enjoying the sensation.

I moved back down now, and continued my massage of her ass and thighs, but this time sliding further toward that warmth between her thighs.

Lisa spread her thighs further and my thumb slid easily into her as the rest of my well oiled hand and fingers rubbed her perineum and asshole.

I switched hands and worked 3 fingers into her with my thumb against her ass as her moaning and pushing back became more urgent. I maintained a firm strong rhythm against her as she bit down on the pillow and pushed back against my hand. She came hard against me, crying out, her wetness evident on the sheet below her.

She regained composure slowly and pushed me down on the bed. She again took me into her mouth, bobbing up and down with a sense of urgency. She stopped to breathe before drizzling oil over those huge soft breasts then began to body slide against me. My cock enveloped in her beautiful breasts. The friction was intense and and I felt my balls tighten as she slid against me.

I came hard. Shooting against her, against me.

She slowed down, I had my eyes closed enjoying the last waves of my orgasm washing over me.

After some time she led me to the shower and gently washed me and then herself.

We dressed and both left the hotel.

This was not the last time we had a business transaction.

***I completely support the decriminalisation of sex work. There are some amazing people in that industry that have helped me tremendously.

Source: reddit.com/r/gonewildstories/comments/eojfou/from_coworker_to_sex_worker_mf