Surviving College Pt. 01

Everyone in this story is over 18.

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I guess what led me to being an escort is a bit of a cliche. Poor college student. Trying to make it on my own. Failing to earn enough money to support myself. A friend told me how they made money. Nothing unheard of.

Except I am a guy.

This is not a story of someone naive. I have always known I am good looking and I worked hard to be that way. People have always let me know it as well. As a child, I was always told how handsome I was going to be. Puberty did not change that. No awkward stages. I sprouted early. I was always comfortable around girls. As the only boy with five sisters and no male cousins, girls were just something I was at ease with. I played sports but was not a jock. I did quite well at school but was not a nerd. I was outgoing but not a showoff.

As I said, I worked on my appearance a lot. Since age 14 I have worked out. Not just weightlifting, but running daily, swimming, biking, hiking. My body showed it. I was 6'4", 210 pounds at age 18. Lean and muscular.

I also knew by then that I had a great cock. It first came up in the locker room, as things like that always do. Some guys are show-ers and some guys are growers. I was both. Limp I was around five inches. Hard about eight. Pretty thick as well in comparison to others. A couple of the guys started joking about my "trunk". It became a joke in the track team locker room. They gave me the nickname of elephant. People would ask what the name meant but I would always blow it off. That stuff always comes out. Some guy tells his girlfriend, she tells a friend, soon a lot of people know. Not that I was complaining.

Even before this I had no problem hooking up. Head at the movies, handjobs at a party, sex was easy. Dated a lot but never had a steady girlfriend. I was "that guy" in high school. I did not want a serious girlfriend. I knew that I could not be distracted. I grew up in a small town north of Boston where most people did not go off to college. They just stayed put after graduation. I did not want that. I wanted to leave.

My family life was less than ideal. My mom and dad got married once they found out mom was pregnant. Mom was seven months pregnant at the wedding. They ended up having six kids over nine years. I came along near the middle. When dad found out mom was pregnant the last time he bounced. Did not hear much from him over the years other than a few cards with a $5 bill in it. I know it was tough on mom but she did not get much sympathy from me. She was not kind and just an unhappy person in life. Always had been.

I decided early in my teen years that I was going to get away and stay away. I studied hard and did a lot of extra-curricular activities. Track, swimming, volunteering, tutoring other students, computer club, fundraising. If a teacher recommended it, I did it. I graduated second in my class, had an amazing transcript. I applied to pretty much every scholarship I could. I got a lot of them as well. I was accepted to MIT with the majority of my tuition covered. I was feeling great.

I knew that no financial support was coming from mom. This had always been understood. The summer after high school was all about working. I had a paid internship with a software developer, I had a job waiting tables at night, landscaping Saturdays and Sundays. I felt confident that I would put away enough money along with having a part-time job during the year.

Freshman year was eye-opening. The course load was brutal. I was struggling hard. I could not keep up my grades. I dropped the part-time job to focus on my studies. This worked. I maintained my required GPA. Scholarships retained. I also completely wiped out my bank account. That was the money I had planned to use over 4 years. Gone.

I had decided to stay in Cambridge that summer. I had a great internship lined up. My friend, Derek, and I had arrangements to move into a shared apartment for the following year. We had a sublet for the summer. And I had also been smacked in the head by love. For the first time in my life, I was in love.

My birthday was two days before the end of the semester. I was basically done. I had one assignment left to submit but it was completed. A group got together to have some drinks and celebrate the semester and my birthday. Drinking some beer and hanging out along the Charles River and just having a great time. A party was happening that night. A girlfriend of a friend of a friend showed up at the river with her friends. Sure, I went to a technology school that was mostly guys, but it was not like I had lived a monastic life for the past year. Random college hookups happened but nothing serious. However, girls at a college party are always an attraction. I was feeling good and had always been outgoing. I chatted with the girls, light flirting. They suggested a different party so a friend and I decided to go with them, bailing on the previously planned party. We decided to walk with the girls to the party but they needed to stop and meet their roommate.

When Ana walked out of the dorm building it was like a scene from a movie. I saw her and everything stopped. I ignored the conversation I was in. I just stared at her. I was floored. She greeted her friends and while they were introducing us she just stared at me. She and I instantly were talking with each other, ignoring everyone else. We walked to the party together and instead of going in with everyone else we stayed out and talked. Nobody else existed for us.

Ana is gorgeous but any measure. Beautiful face, blue eyes, 5'10", dirty blonde, slender and athletic body, long legs, full breasts, incredible ass. Model hot. Physically incredible.

Conversation came easy to us. We sat outside talking for an hour until one of her friends came out and asked if we were coming in. I was about to say yes when Ana said no, we were going for a walk. I definitely was not going to disagree. She and I spent the evening walking and talking. At some point we started holding hands. Kissing followed shortly after. I was hooked and it seemed that she was as well. Soon it was late. She said she wanted to go back to her dorm. I was bummed because I did not want to end our night but I understood. Back at her building I gave her a kiss, thinking it was the end of our night, but she told me to come in. Kissing and undressing and admiring each other turned into love making first and then fucking. It was an incredible night. Waking up with her was a dream.

We had similar backgrounds. Not a great family life. Paying our own way for school. Both feeling that we were responsible for our futures, not relying on others. Shared interests with just enough differences to be interesting to each other. Sexually we fit together as well. Experienced and focused enough on each other's pleasure to make it incredibly pleasurable for ourselves. We fit each other.

Ana and I were together from then on. We spent our free time that summer together, getting to know each other more, sharing ourselves. Six weeks after meeting, I told her I loved her and she said the same. It was perfect. The summer passed quickly, both of us working a lot.

The new semester began, I moved into the new apartment with Derek. Money was tight but I was feeling confident in my studies and I picked up a part-time job waiting tables and tending bar a couple of nights a week. I was making enough to survive but was rapidly depleting my savings from the summer. I was not living extravagantly but college life is expensive. Ana was in a similar situation. We were surviving.

I came home exhausted one Tuesday evening in late October. I had been up at six that morning. A run to start my day, then classes, then a shift at the restaurant. The shift was busy but I made terrible tips. The diners had all been cheap. I was feeling a bit defeated. Derek asked if I had a moment to talk. He explained that he was failing school and was dropping out. He was moving out of the apartment at the end of the month, just nine days notice. I was furious, nervous, scared. There was no way I could afford our apartment. I would be able to cover rent for November and December but that would wipe out my bank account completely. I was upset with Derek and I walked out. I went to visit Ana at her place. She listened to me vent and she comforted me.

Ana lived in an apartment with three other girls. One of her roommates, Erica, had the solution. She had a friend who needed an apartment. It seemed perfect. The problem that I saw was that this friend was female. I knew that I would not cheat on Ana, but I did not want there to be any cause of a rift for us. Ana knew I loved her and she said she would not be jealous. I was very hesitant. Ana made me promise to consider it.

A few days later, Ana and Erica came by with the potential roommate, Rachel. Rachel was 23, seemed cool, had her shit together, was a graduate student at Harvard, worked a lot, did not party. We got along, Ana liked her, Erica vouched for her. She was the perfect roommate. The downside was Rachel was also really fucking hot. Short, dark hair, dark eyes, olive skin, curvy, huge boobs, big ass. Everything about her was sexy. She was also single. I could see potential problems with jealousy. After Erica and Rachel left, Ana asked me my thoughts and I was honest with her. Ana asked me if I thought I would ever cheat on her and I assured her that I would not. She said she was confident in me. She knew that I had had opportunities in the past, whether at a party or from the restaurant to cheat and I had always been forthcoming with her. I knew the same about her. We decided that I would offer the apartment to Rachel.

Rachel was excited. She had been crashing on a friend's couch. When I suggested she could move in immediately, she accepted. This was working out great for me. Now I would not be wiped out financially.

I told Derek that I had a roommate lined up and he moved out that weekend. It was tough. He was my best friend and he knew he was abandoning me. I helped him pack and we talked a lot. I understood what he was going through and I recognized how badly he felt. I let him know that he was still my friend and that the situation would work out for me. I wished him the best and assured him we would maintain contact.

Rachel moved in at the same time Derek was moving out. I was impressed by Rachel. She was organized. She had movers deliver all of her stuff that Sunday morning. She had hired a cleaner to come in advance and had the apartment sparkling. Derek and I were not slobs by any measure but having a cleaning service come through was a surprise. Most of the furniture Derek and I was secondhand, a bit ragged. Rachel had nice furniture. Her bedroom furniture was obviously expensive. She asked me if I was ok with getting rid of the existing couches and chairs and using hers. Of course I was fine. I had figured that hers were probably nicer. I had no idea how much nicer. Modern, high end furniture. I was shocked. Nothing was cheap. Definitely a big upgrade. She was moved in and unpacked by that Monday evening.

The following Wednesday was Halloween. Ana and I had dressed up and went to a party. Nothing big, just some fun. When we came back to the apartment, Ana was in awe. She had not seen the change of the furniture. She explained to me how expensive it was, all mid-century modern furniture, none of it knockoff. We had known that Rachel was in good shape financially, we just did not know the level of luxury that she was living. I was enjoying it.

Rachel settled in, we barely saw each other. I was up early to work out and then working late at the restaurant. She was usually asleep when I left in the morning and at work when I got home. We would pass by each other, friendly conversation. She had told me that she was a hostess for private events. She worked four nights a week, Thursday through Sunday. Spent the rest of her time studying. Life went on for me mostly as it had been.

The new semester brought new problems for me. Classes were more difficult but I could not afford to work less. Again, my grades suffered. Ana was also have similar problems. We were both struggling financially. Ana was possibly going to have to move from her apartment. She had an aunt that offered to let her live with her, but that was a 90 minute commute. Her roommates were understanding and said they could find a replacement for her. One evening we were in the living room when Rachel overheard us talking about the potential move. Later, after Ana left, Rachel asked why I did not invite Ana to move in. I was surprised at her suggestion. I had thought about but I did not want to put Rachel in an uncomfortable situation. Rachel assured me that she would be fine with it. She enjoyed having me as a roommate and Ana was already spending several nights a week, why not make it permanent. The next day I brought it up and Ana accepted immediately. She moved in on March first.

The change in living arrangements was seamless. It alleviated the financial stress, splitting bills three ways was a win for all of us. The remainder of the semester went well. Or it seemed to. My grades had suffered and I lost one of my scholarships. Not a big one but enough to be a worry. On top of this, my new summer internship was a lot more demanding. I was not able to work as much at the restaurant. By July it was apparent that I was in bad shape for the coming semester, I was just not saving enough. Ana was working a ton but also had her internship to worry about. I could not rely on her to make up my financial shortfall since she had her own money problems.

By this time Rachel and I had become quite friendly. She was still guarded concerning her personal life though. I decided to talk to her, ask for some advice. I told her everything. She was understanding. She said she had gone through the same situation. I asked how she had solved it. She said that she felt comfortable enough with Ana and I to tell us. She suggested that the three of us have dinner on Wednesday night to discuss.

I had assumed that I would cook us all dinner at the apartment. When I got home from my internship, Rachel told us to get dressed up for dinner at a nice restaurant. I dressed in nice pants, button up, nice shoes. Really the best outfit I owned. Ana was wearing a nice evening dress, heels, and makeup. Dressed to the nines for college kids. Rachel came out and we were blown away. Dress, shoes, jewelry. Obviously a very expensive outfit. It made Ana and I feel like we were wearing rags. Rachel told us a car service was picking us up.

As we went outside, a Mercedes S-class pulled up. I was in shock. The girls hopped in the back and I sat in the front. Rachel just grinned at us. We arrived at the restaurant, L'Espalier. I had heard of it but could never imagine going there. I had just turned 20 and could barely afford cooking at home. We were seated and Rachel said that she had ordered the tasting menu for the three of us and she would explain everything after we ate. My mouth was agape the entire time. I barely remember the dinner. Eating food that I could barely pronounce. Wine that cost more than I made in an entire shift. Ana and I tried to ask Rachel questions but she just put us off by saying later.

A few hours later, sated and slightly buzzed, we were back in the car, heading home. Once in the apartment, Rachel told us to sit. She showed us the receipt for dinner, $900 plus gratuity. She said that she had meals like this often, several times a week. I told her I felt very uncomfortable that she had spent so much money on us. She said she did not pay. She began to explain that it was paid for through someone she knew through her job. She was not exactly a hostess. She worked as an escort through a private club. The club focused exclusively to high end clientele. Ana and I were surprised, obviously. But things began to make sense. Rachel never seemed worried about money. Everything she owned was the best.

This explained how she was financially stable but did nothing to solve my or Ana's problems. As she continued telling us details, I began to get upset, I was feeling that she was recruiting Ana. I was then blown away when she said she could potentially get both of us work there.

Ana and I were not innocents when it came to sex. Neither of us were virgins before meeting, we had many sexual partners. We had a very active sex life. We experimented a lot. We have had multiple threesomes, with other women and men. We had both had bisexual experiences. Neither of us were shy about sex. Nor were we shy about talking about sex. But the idea of sex work was something I had not considered. Judging from Ana's face, neither had she.

Rachel explained details of how the club worked. The club arranged her dates. The club handled vetting. The clients were exclusively wealthy. New clients were referrals only. She made it seem so simple. She said that many clients would like to meet couples, like Ana and I. She said that we could work together. That many people would pay just to watch us have sex, that might not even join in. Rachel told us that she knew we had sex a lot, a couple times a day. She said that she had three regular clients per week and two or three random. All of the clients were significantly older than her. Many of them men in their 50s and 60s. Then she told us how much she made. She was making between $4,000 and $6,000 per week in cash. She said that this was pretty normal for most of the girls that worked there. She said it would vary for us since we were a couple and depending on what we were open to doing.

Holy fuck. That was all I was able to say. Ana was silent. Rachel had been pretty detailed about the money end of it and what she did for it. It was not only sex, sometimes it was just companionship, but it was mostly sex. She asked us to think about it and if we had any questions to ask her. She said goodnight and went to her room.

Ana and I just stared at each other for a moment before I said we should go to our room. Once inside, I asked her what she thought. She said she was amazed that Rachel did that. I told her if I were not in a relationship with her, I would not have a problem doing it. She said the same for her. I asked if that was something we could do being together. We had already had partners join us. The major difference being that we picked up those partners or those partners had flirted with us.

As I said before, we had both had bisexual experiences but mine had always been as a top, mostly having my cock sucked and occasionally fucking the guy. I had given a guy oral a few times but had never been fucked. The age difference of the clients seemed to be the biggest issue. Would be have any attraction towards them? What would they expect from me? We discussed this for hours, just sitting on the edge of our bed, still in our evening clothes. Finally, around three in the morning, we were yawning and got undressed. Ana went to the bathroom while I got in bed. I lay there thinking. I loved Ana. We were both desperate for money. We both were good students that were struggling in school because of finances. The only issues we ever had were due to money.

I looked at the clock and saw it was almost four. Ana had been gone for almost an hour. I put on a pair of shorts and went to find her. I figured she was in the living room, thinking. She was not there, or the kitchen, or the bathroom. Walking by Rachel's room, I noticed her light was on and heard low talking. I decided to tap on the door. Rachel told me to come in. She and Ana were sitting on her bed. Ana had obviously been crying. I gave her a hug and sat next to her. She just burrowed her face into my shoulder.

Rachel started by saying that she did not mean to upset either of us, she just wanted to offer the solution that she had found to her problem. She then said that Ana had been saying that we were both interested but she did not want me to think that she was a whore. I laughed and said that we were both in the same position, why would I think differently of her. We chatted more and realized that we were both open to trying it. I asked Rachel what the next step would be. Rachel said she would need to show her boss photos of us. She told me to go shower and shave my scruff. When I came back Rachel sent Ana to shower and put on some makeup.