My husband and I got involved in the lifestyle in 1992. After a few months of giving blowjobs to his friends (and later on being fucked by them) we decided to check out a few of the lifestyle clubs and parties in New York. We attended a couple of events, and were generally unimpressed. Met some very nice, open-minded and uninhibited people, but 99% just weren’t what we were looking for.
One guy came up to us at the first party we attended, and we chatted for awhile. His interest was obvious, but my husband politely declined, which is more usual in the lifestyle than you might imagine. He just wasn’t my type.
We saw the same guy at some other clubs/parties, and he always stopped to chat and say he was still very much interested. Always pleasant, never pushy, but definitely tenacious! We started to refer to him as “my biggest fan”, and knew he would approach us at any get-together. He wasn’t desperate – he was a decent looking guy, and we always saw him getting action at these events. Again, just not a match for us.
After about 6 or 7 meetings, we were chatting while having a drink at the bar and enjoying the people-watching in the room. He turned to my husband and said, “Look, I know I’m being a pest, but what would it take to get me with your wife?” My husband turned to me with a look that said, “well?” I didn’t want to be rude to the guy, so I jokingly replied – $500. I got the shock of my life when the guy replied, “Deal!”
Now at the time I was working a job where my take-home for the week was about $385 after taxes. $500 was a lot of money to 27 year old me. My husband was laughing, expecting me to tell the guy I was joking, and I think I shocked them both when I asked, “Where and when?” “Right now in the hotel across the street”, was his answer.
I was half naked anyway, so definitely looked the part. The lifestyle events always had condoms handy (safe play is always encouraged), and I had a cocktail or two in me. “OK, boys, let’s go!”
We walked across to the hotel where the guy quickly got a room. I think they knew about the lifestyle parties across the road and did a good business on those nights. We went up to the room, and Bill, the “customer” handed my husband $500. “Guess you’re playing the Pimp Daddy tonight!” My husband asked if I wanted him to stay or leave us alone, and Bill said he definitely enjoyed an audience. Settling in on the couch in the room, my husband sat back to enjoy the show.
Bill was about 10 years older than me. He took off his shirt, revealing what would be called a “Dad Bod” today. Solid, but no real definition. A slightly hairy chest and abs, which is honestly a turn-off for me. I like smooth, hairless bodies, and have never been attracted to “furry” guys. But my thought was, I had basically accepted a “job”, and now I had to fulfill it. My outfit was barely more than lingerie. A lace bra top and thong with a mini-skirt over it and a pair of stripper heels was all I had on. Undress to Impress is the lifestyle motto!
Considering Bill had just “rented” me, he was a gentleman. He asked what my limitations were (no anal, condom for penetration, and nothing rough), then started kissing me as he reached around to undo my skirt. It fell to the floor and I stepped out of it, tossing it to my husband, who gave me a wink. Bill grabbed my ass and pulled me against him, and as we continued kissing I felt his erection pressing against my stomach through his pants. I have to admit it felt pretty impressive. After a few minutes his hands slid up my back and he undid my bra. It joined my husband on the couch, and Bill began to knead my breasts, rolling my erect nipples between his fingertips. His mouth followed, and be began to lick, suck and nibble on my breasts. He was very definitely a breast man, and gave them a lot of attention.
“Take off your panties,” he directed me, and they joined the collection. He sat on the edge of the bed and told me to stand facing him with my legs apart. So I’m standing there in just my heels when he directs me to start touching myself. Now to be honest, I’m not much of a masturbator. I’ve always had hubby (or another guy) to pleasure me, so rarely had to take matters into my own hands. I cupped my breasts and slowly slid my hands down my body, then put a finger between my legs, where I was honestly surprised to find how wet I was. Gently stroking my clit for him, first with one and then two fingers, I began to moan in not-so-simulated pleasure. My other hand was running up and down my body. “Don’t cum”, Bill directed. I dialed it back a bit, then was told to lay on my back on the bed and continue touching myself. As I did so, Bill unbuckled his belt and dropped his pants, displaying a thick 6″ cut cock. While not totally shaved, his cock and balls were trimmed short, much to my relief.
He kneeled on the floor, pulled my ass to the edge of the bed, opened my legs and started licking. He was talented. You could definitely tell this wasn’t his first rodeo. His tongue worked magic on my pussy, bringing me to a sudden, unexpected orgasm. My husband said I flushed bright red from my nipples up to my face when I came. “My turn now”, Bill said, and stood up. Taking my cue, I sat up, with Bill’s cock bobbing directly at mouth level. I must have been in a post-orgasm rush, because my husband said I didn’t tease it, I devoured it. It may have been about an inch shorter than my husband’s cock, but it was half again as thick. My lips stretched over it and I worked it hard. “Fuck, you’re a good whore”, Bill said, and that made me double my efforts. “You like it, baby?”, I asked, rolling my tongue around his thick head. “You getting your money’s worth, Daddy?” His groans of pleasure told me he was.
Now, I have to admit I was hoping he would cum from my oral and we’d be done. This cock was thick, and my pussy was (and glad to say, still is) tight. Girth like this was going to be a stretch. But he pulled his cock out of my mouth and told me to get on all fours. Reaching for a condom, he said, “You ready to get fucked, whore?” All I could think was – 1) Yes, I’m a whore; and 2) Yes, I’m ready to get fucked.
I felt the head of his cock against my pussy, and let out a loud gasp when he suddenly drove it balls deep. Luckily I was still wet and the condoms had lube. Bill said, “You like that, whore?”, and began thrusting into me, hard strokes that had me grunting and yelping with each thrust. The girth of his cock made a tight fit, and I was feeling every bit of the power behind his thrusts. “Yes, Daddy, fuck me hard!”, I managed to get out, just before I gave a loud orgasm. He pounded me in this position for almost 10 minutes, but it felt much longer! I was sweating, he was sweating, and you could hear the wet suction of my pussy being violated. Finally I felt his grip tighten on me, and he let out a huge groan as he came. His weight dropped on me, and I ended up flat on my stomach, him on top with his cock still twitching inside of me.
My husband finally spoke up, saying that the show was amazing. Bill rolled off me, and said, “That was worth the wait and every dollar! Same time next week?” My husband said, “Sure, but no discounts!” As the guys discussed the fact that I was now officially a sex worker, I went to take a shower. It surprised me how little I had to fake the pleasure. Yes, Bill wasn’t a guy I would choose to fuck, but if the offer was repeated I would do it again. And it sounded like that was the plan. It dawned on me in the shower that I had just made more money in an hour than I had in a 40-hour work week. Could I repeat this with other guys?
After Bill got in the shower, my husband helped me get (semi)dressed again, and gave me a deep kiss telling me how proud he was of me. “And you made $150!”, he said. “Wait, I saw you get $500 from him?” “Yes, but the pimp keeps 70%, remember?”, he said as he kissed me again. He was just joking, but it definitely set the dynamic for us.
The 3 of us went back to the club, getting some knowing glances as we walked in together. “So if anyone asks, are you on the game now?”, Bill asked. “I guess?”, I said, looking at my husband, who gave me a nod. I knew there would be lots of discussion about this in the next few days.
And there was!
Source: reddit.com/r/gonewildstories/comments/103b6na/how_i_became_an_escort_f
Great story!
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