My First Time With a Sex Worker

By Kendra Holliday | December 25, 2014

Are you ready to check one of these out?

Are you ready to check one of these out?

A lot of men don’t have ready access to sex. I always suggest seeing a sex worker as an option. Some men are open to the idea, but some say they would rather suffer with celibacy the rest of their lives than stoop to that level. There’s so much stigma attached to it in our society!

I’m giving a Sex Worker Talk for Men Only on January 5. At the talk, I will answer questions about sex work (How should I interact with a sex worker? What if my partner is a sex worker? Can I be a sex worker? How do I stay safe?)

Recently, I counseled a married man who hasn’t had sex with his wife in three years. They have a great marriage with two young children. He loves his family dearly. In their case, he does not believe that sex is a barometer of their relationship. His wife is getting her physical and emotional needs met. He is getting his emotional needs met. But the lack of sex is really stressing him out! He’s been to therapists, couples counseling, she’s seen doctors…

So, he’s turning to sex work, and during his research, he found me and my unconventional methods. As he left our talk, he already looked like a different man – beaming and relieved – just thinking of all the possibilities most people won’t even consider.

Which brings me to this. A friend of mine in Florida tried seeing a sex worker for the first time last week. I asked him to share his story with my readers. Here it is! ENJOY this wonderful gift.


I never expected to spend part of my evening with an escort.

It had been over three years since my last sexual experience, and longer than that from my last satisfying sexual experience. During that time, I had been meeting plenty of women and dating quite a few of them, but none of them seemed to be interested in me beyond platonic friendship.

After the last “let’s just be friends” conversation I found myself at loose ends, with no prospects in sight, at a time when my long shut-down sex drive was coming back with a vengeance. That’s when I realized that the possible solution to my long sexual drought was right in front of me. I could have a session with an escort.

Before taking the plunge, I took a lot of time to do research. The sex industry, as all TBK readers know, exists in a very gray area of the law, and, because of that, there are no consumer protections for customers (or protections for the providers, for that matter.) Ripoffs and poor service are all too common. Escorts cannot offer sexual services directly, so I had to become very good at reading between the lines on their ads. Along the way I discovered the USA Sex Guide (USASG) and The Erotic Review (TER), sites that became indispensable resources for my research. TER in particular is very useful, having comprehensive review coverage, and also including some great FAQs to help those new to the scene.



But it was the message boards at USASG that uncovered a gem: Rachel, an escort new to the scene working in a major city just to the north of where I lived. Men in the message board were positively gushing about her, in particular talking about how sweet, gentle, and unrushed her sessions were. I am very much into affection and touch, and I knew I had found my woman.

We made contact by email–unlike most escorts, Rachel did not post a phone number in her ad–and set up a time. She sent me her phone number so that we could text on the appointed day.

I was passing through her city on the way to another event, so I set the time for earlier that same day. In the days leading up to our session, I had a real feeling like a kid anticipating Christmas. The drought was about to end–I would have sex–and it had a date and time! It was all I could do to keep myself in the present moment in the days, then hours, leading up to our session.

I drove to the city to an independent bookstore close by her incall location and texted her to let her know I was there. She replied that she needed to start a bit later than our agreed-upon time, which was okay with me.

Her incall location turned out to be her home, in an older but nice neighborhood. The door was open to her place, and Rachel greeted me in a sheer robe. I took note of her tall, slim but shapely figure, and sweet face, and immediately felt the warmth and gentleness from her that the USASG posters had written about.

We kissed, and not just a little kiss, but an actual deep French kiss! Her Rottweiler greeted me as well–possibly the mellowest Rottweiler on the planet. We sat on the couch to talk for a bit.

I left the donation on the coffee table with no fanfare or fuss, just as protocol demanded; she didn’t pick it up or look at it. (This is done to avoid the appearance of directly paying for sex.)

Rachel showed me around her small but comfortable apartment, took me to the bedroom, and invited me to “get comfortable.” I took off all of my clothes. Since we were starting with a sensual body rub, I then lay face down on the bed. She took a few minutes to come in, and then we got started. The body rub was not like the professional massages I had received in the past; it was more touch, and visited areas LMTs don’t visit. In addition she added some sensual touches like sucking on my fingers and nibbling on my earlobes. It felt great, and it was a nice way to open our session.

Rachel invited me to turn over, and when I did, I found her with no clothes on, lovely 34C or so breasts in view, and with a very neatly trimmed bush. She started a blowjob, which made my fingers curl. Her technique was excellent; I never felt a tooth so much as graze my cock, and she added plenty of suction.

Unfortunately, the “little head” had other ideas, and obstinately refused to get hard. Rachel was determined, and tried different positions, varied her suction, rubbed my balls and perineum, to try to get things going, but there was nothing doing.

I drew her mouth away from my cock and towards my mouth, and we kissed. “You can always take the initiative,” Rachel said, gently. I realized had just been laying there. I kissed her. Passionately. Took her head in my hands and really kissed. I rolled us over. My hands went everywhere, breasts, waist, belly, thighs, bush. Finger on clit, some moaning; fingers in vulva, lots of moaning. Fingers moving in vulva, more moaning……..

….and as I did this something stirred inside of me that had long been dormant, through not just the three years of no sex, but the years before of bad or indifferent sex. It was a feeling of total freedom, of having this sweet and very willing woman with me that I could totally explore. I was hungry. I couldn’t kiss her enough, and Rachel was responding. We kept going. 69. Then her going down on me again. Then me going down on her.

Gradually the intensity began fading, but we were still in each other’s arms, talking to each other between kisses.

“You know what I love to do, Rachel?” “What?,” she said. “Get into bed and spoon, and sleep with a girl like that, all night.” She smiled and moaned, then rolled on her side and presented her back to me.

I curled up behind her, and as I took her in my arms a huge wave of emotion started. “I’ve missed this so much,” I said, as the tears started. I couldn’t believe how incredibly good she felt, and how much I had needed this, and she was so sweet with me, holding me as the tears came.

Eventually, I settled and felt so calm. Rachel stirred in my arms. “Would you like some ice cream?” A bit nonplussed but curious, I said yes, I would.

She left the bed, returned in a few minutes with Ben and Jerry’s with some Heath bars crushed inside. She curled up on me and began feeding me bites, then turned around to nestle in my arms, feeding me bites over the shoulder. I took the spoon from her and began feeding her bites, then immediately kissing her to try to get the “snowball” effect. It became a game–try to catch the snowball before one of us swallowed–and we laughed.

At one point, I accidentally dripped some ice cream on her chest, and went to lick it up, her playfully accusing me of doing it on purpose. So I started doing it on purpose, just because she said I was! I licked ice cream, and we laughed–and kissed.

Time lost meaning. I was sure we had gone past the hour we were supposed to have, but Rachel didn’t seem hurried at all. We kissed and touched some more, and I thought, as much as I didn’t want things to end, that I should be respectful of her time.

She appreciated it, but we didn’t exactly hurry out of bed. When we did finally get up, she went on her knees one more time to give me a blowjob, and try to get me to orgasm, finally, but the little head remanded obstinate.

Rachel kindly offered her shower so I could freshen up for my event that evening, in a small but very clean and inviting bathroom. I showered, feeling like I was in a dream, and came out to find her in a silk robe, arms open for me. We kissed, and kissed, and I finally said I had to go, but wanted one more big kiss. It took several minutes, and I finally, playfully yelled, “BREAK!” as I disengaged from her. I said good night, and left.

My session started at 5:15, exactly on time. I checked my phone in the car. It was ten minutes to EIGHT! She had given me over two hours, two very wonderful hours. I was so overwhelmed that I had to literally talk myself through driving on my way to my event.

Later, I needed to stop at the store to pick up some wine. As I entered the store, there was a literal tingling in me, head to toe, which I had not known in so long I had to think about placing it. It was perfect, wonderful contentment.

Rachel had given me a truly incredible and magical time–and there was room for it to be even better next time. I cannot even begin to express my gratitude to Rachel, who turned out to be perfect for me, on this, my first time with a provider, and my first time back in bed in years. Even now I still feel the waves of contentment.

– Creideiki


youknowme 2014-12-25 08:54:56

Absolutely beautiful! I shed a tear of joy for you! Thank goodness for the Rachels of this world and men like you.


    Creideiki 2014-12-25 11:06:40

    Indeed! I believe that out of 500 providers I couldn’t have found one that was more perfect for the moment I had. Rachel is truly special.

    How times change: Before I saw her for the first time, I hadn’t had sex in three years. I’m now 9 days away from my second visit with her, and that is already feeling like an eternity! Thank goodness that I have lots to do, so that the ensuing time passes quickly.

    I’m still on a high from the first time–and I didn’t orgasm on that first time. I almost can’t get my mind around what it will be like when I do!


Gary 2014-12-25 12:23:01

I would recommend a sex worker even for some men who have “ready access to sex”, namely the pick-up artist who fools naive women into thinking they’re getting something they’re not. I’d prefer the honest interaction with a sex worker to breaking a woman’s heart and feeling like a turd.

Reminds me of an old joke: Who says you can’t get laid with a Toyota Prius? With the money you save on gas you can get a prostitute!


    Creideiki 2014-12-25 16:12:18

    As it happens, I drive a Prius. While I’ve been friend-zoned over and over, I don’t think it was the car that did it. In fact, I had one drop-dead gorgeous woman compliment me on my car choice.

    But yes, I spend a lot less on gas than many. With the money I save, I can afford providers from time to time!


Anna 2015-01-02 16:16:47

As a sexworker reading this, i cant help but feel that potential clients reading this may expect exceptional service to include a lot of extra time. I would never work for 3 hours for a 1 hour fee… Seems like bad business to me.

My sessions are never rushed, but goddamn….i couldnt afford to give away so much free service. I got tuition to pay! haha


    Kendra Holliday 2015-01-02 18:16:32

    GIRL, I hear you! I felt the same way! I don’t mean to be a clockwatcher, but I do need to keep on schedule since I host so many events, have a partner and kids, etc. So if someone stays longer, I do hope they tip/consider my hourly rate.

    In fact, I encouraged my friend to tip this woman the next time he sees her! She is going above and beyond in her healing work! Maybe she doesn’t have kids, partners, school, day jobs, and events to tend to?


      Anna 2015-01-02 21:05:14

      Yeah, honestly…..his account almost reads like fiction. Its hard to imagine somebody who doesnt value their professional services enough to charge appropriately. Maybe she is fabulously wealthy and does this just for fun? hahah


        Sandy 2015-01-03 15:43:33

        Yes, it does sound a bit fictional. Heck, I was lucky to get 3 hours like that with my wife even in the best of times — even if I did all the chores and gave her a candlelight dinner! LOL


        Creideiki 2015-01-04 21:45:45

        I did have a second session with her yesterday and this time around Rachel was much more mindful of the time because she had another client after me. The first time I saw her, I was the last session of the evening. Even still I was stunned at how much time she gave me that first time. I don’t think that’s something I will see again from her or any other provider.

        I did tip her, plus I brought some yogurt she likes from Trader Joe’s (I have a TJ’s, but she doesn’t) so hopefully that was some compensation!


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