Monetizing Hand Jobs

I find myself in my late 20s with my first serious relationship. Finally, after a really really long time, I am comfortable sharing private aspects of my past life. I did have two boyfriends in high school. High school dating wasn't bad, but it certainly wasn't a positive experience. Consequently, I went through college, and for the last several years, absent from dating.

Recently my current boyfriend and I were talking politics and the topic of decriminalizing sex work came up. As an esoteric question, he asked whether I would ever consider being paid for sex. At the time I didn't think it was so controversial. So I honestly responded by stating that depending on how you define sex I already have.

That response surprised him. To his credit, he was more inquisitive than shocked. Instead of merely summarizing my past during that conversation, I am writing my reflections for a more complete explanation.

It was my third year of college. I went to a small liberal arts school; and when I say small, I mean 2000 students. It was a great experience even though I needed to work nearly full-time to pay my way. My financial need to work limited my campus socialization, which was fine because as I said, high school dating did not encourage me to date through college. I worked, studied, and focused on school as opposed to casually dating.

Utilizing my experience as a big sister, I started cutting hair for a few friends. Eric was my closest friend and we both held the same views on dating. He also focused on school over sexual relationships. His friendship meant a lot, and he supported me in many ways.

I got in the habit of giving him a scalp and shoulder massage after I cut his hair. He would give me a simple $20 for each haircut knowing I could use some extra cash. A lot of people enjoy scalp massages. Eric found these especially calming, and at least once got aroused. I teased him about visually noticing his erection. We are not shy around each other so he quipped back that he was sure my hands would be exceptional for hand jobs in addition to massages. This is where we may have been too close and casual as friends. I was standing behind him. I slid my hands down his chest, and maybe quicker than I anticipated, shoved my hands into his pants. He was extremely hard, and he must've been for a while judging by the presence of liquid-like pre-cum.

I should note by this point that I had very little experience touching penises. I did have sex with the two high school boyfriends, but it was mostly them just jumping me for their own pleasure. I experienced very little foreplay or touching.

So when I touched Eric, it was much more intimate than I had expected. I may have been Ignorant but what was intended to be playful and joking was quite arousing. We could have been more reserved as friends. Since I went for it and had my hands down his pants, Eric encouraged me to continue. I explained that I didn't know what I should do. I also wanted to protect our friendship, My curiosity about experimenting with him was real. He joked about increasing my tip for the haircut if I didn't stop.

I moved a chair next to Eric as he opened his pants and I sat next to him stroking my first erection. It was the first erection that I felt with my hands. It may have been the intimacy of the haircut and the massage, or it may have been the surprise of how quickly we got into this situation, but it all went very fast. I was going to reach for some lotion when he started wiggling and told me he was cumming. What a shock and a huge mess. I've seen some porn videos, but never have I seen so much cum. It was all over his shirt and his pants.

I was surprised at how good I felt. Euphoria was how I would describe it. And since I never undressed or was touched, I didn't feel violated either. It was like giving a massage; something fun I could do for a friend. And he was so appreciative since he also does not have a dating life to satisfy his sexual drive.

We cleaned up and talked as friends to make sure everything was good. And when he paid me for my haircut, he gave me an extra $20; which was all he had. $20 wasn't significant and I did it just as friends. Yet the symbolism of accepting money gave both of us a pause. I could use the extra cash since I was on a shoestring budget and ultimately it gave the experience just a bit of a torrid excitement.

He joked that maybe he would get his hair trimmed more frequently, which I encouraged both for the money and the fun

That first $20 was somewhat transformative although at the time it still felt like a one-time transaction. That was until the following week when Eric came back with a radical offer. Eric, like me, was not from money. He did however end up in a circle of unusually rich friends. A few years back, a huge name in economics arrived as a professor at this little school for personal reasons. He was revered in the Wall Street circles, and as it turns out a group of Wall Street tycoons sent their kids to this otherwise non-prestigious school just to study under this economist. We were too small for the traditional fraternity system, So roughly 20 of these elite students lived in the same dorm and formed their own private society as a brotherhood, instead of a traditional fraternity.

Eric kept my name secret as he shared the concept of a haircut and hand job with just a few close friends. They loved the idea. They liked the erotic nature of it. And they were used to being able to buy fun experiences. So Eric asked if I was willing to take on additional clients. They needed haircuts anyway and that would be the public perception of the interactions. He didn't give me the price but said they would have way more money than he had and it would probably lessen my need to work so many hours.

I had already accepted $20 for my sexual services, so the hurdle of being paid was already crossed. And it was erotic fun. After some contemplation, I permitted him to confidentially send me one of his most trusted friends. A day later Roger scheduled a haircut. I knew Roger about as well as most students in the small school. The low-level acquaintance made it a bit awkward but the conversation was good and we started with the normal haircut.

After I swept up the hair, I gave him my normal scalp and shoulder massage. We then confirmed that he was interested in my hand job services. I trusted Roger. He was nice and didn't demean me at all. He seemed genuinely intrigued to be entertained by his bulging erection. So by the time he lowered his pants, we were both excited. I had done a little research on the Internet and was more prepared this time. We moved to a couch, and he laid down in a better position. And I had lotion readily available, along with paper towels. He touched my back and lightly caressed my arm as I brought him to climax.

Roger was very polite and never attempted to touch anything I didn't want to be touched. The session lasted longer than Eric's, which made it just that much more enjoyable for both of us. I was prepared for the ending, which was just so much more enjoyable to watch. Roger gave me all kinds of compliments. He thought the whole exchange was the coolest thing he had done in college. And this time in addition to the $20 for the haircut, the tip was $80. I made a quick $100 in less than an hour. And had a lot of fun.

He shared some about his secret society, which was just really a bunch of rich kids hanging out and spending money. He also said that the entire group was capable of maintaining secrets. If I was willing, he would bring one friend at a time. And zero people outside of this exchange would know anything is happening beyond the haircut. Now that my rate was established, I cautiously gave support to expand the invitations.

Before the first semester of my third year was over, I had a clientele of about 14 boys. Some planned monthly haircuts while others said they intended every other week. They all knew their privilege, and once they understood my financial situation they were interested in ensuring I had a revenue stream that seemed legit to their parents. $100 for a haircut was a normal cost for these people. Some accepted my services as a means to give me money for school that didn't feel like charity.

Some weeks were busier than others. I earned $600 on my best week. This allowed me to quit my other jobs and increase my studying time. It also expanded the number of students that I knew closely.

All of my rules were honored. I was never propositioned to do more than I offered. I became close friends with some of the boys. A few had girlfriends, which bothered me a bit. I knew our arrangement wasn't a competing relationship and thus, I allowed them to navigate their freedoms. They felt it was just a good way to enhance their college experience and reduce the pressure they gave their girlfriends. Whatever, it was what it was.

It was probably good that it only lasted two years. Into my senior year, I started expanding my boundaries. With a few of my preferred clients, I did remove my shirt for even higher tips. Beyond the extra money, I was getting a thrill. I only removed my shirt for the guys I felt the most attraction so it was mostly self-serving. The enhanced ego trip was exciting.

With repeat clients, I learned each of their preferences and accommodated specific techniques. This earned me even more referrals once they recognized they were getting customized services.

Twice I gave hand jobs to two guys at the same time. They thought that was the coolest thing they experienced in college.

One boy had a very open-minded girlfriend. She enjoyed fucking but didn't know much about foreplay. He told her about the haircut and handjob service. With my permission, he introduced us. They paid me twice to give her hand job lessons. She was way more sexually experienced than I, yet I had something new to teach her. She wanted me to lead a group class with her girlfriends but I graduated before that got arranged.

That's the summary of how I sold sexual services for two years of my life. My grades improved and my student loans were reduced. I learned a lot about sexuality without the daunting commitments of dating. I saw more cum than you would expect since I didn't have actual sex my entire college years.

I offer the story as the explanation for my answer about taking money for sex. Hand jobs are sex. Hand jobs are also fun and can be contained within newfound friendships. I think most relationships are somewhat transactional. And that understanding doesn't lessen the value of any of them.

This experience is part of who I am. This experience helped me develop into the sexual being that I am today.