Surviving College

Everyone in this story is over 18.

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Mid-afternoon and the T was quiet. We sat down and I tried to chat with Rachel. I was nervous about the interview and I was upset about what had happened between. And unsure what actually had happened between. I wanted to ask her but she shut me up by saying not on the train. We rode in silence. I realized I did not even know who her boss was. Guy? Woman? I remembered that she had talked about a woman handling the client bookings but I was unsure if she was the boss. The ride was quick, thankfully. I was surprised when we got off at Park St. Right next to the state capital building. My wind was all over the place. A sex club here? Close to the capital? We headed across the Common, towards Boylston St. I couldn't imagine where we were heading. Rachel went up the stairs of a brownstone and pushed a button. We were buzzed in quickly. We went in the second door down.

We entered into a large room set up like a lounge. Rachel sat and said that George would be with us shortly. I assumed George was her boss. I just nodded. My anxiety must have been obvious. She squeezed my thigh and told me to relax. A man walked in then. Grey hair, maybe 5'7", slight build, very nice suit. I would guess in his 60s. He greeted Rachel and then introduced himself as George. I stood to shake his hand and he remarked on my height, saying that I would be popular. I had no idea what to make of the comment. Rachel turned and gave me a hug and kiss on the cheek and then said she had to go for her date. She said she would call me when she was done.

George told me to follow him. We went into a kitchen and he offered me a water to which I nodded. He laughed loudly, told me to relax, he understood how nervous I was. I realized I had barely spoken and that I was parched. I guzzled half of the water and laughed as well. My hands were shaken. He assured me that this would be the most relaxed interview that I would ever have. I finally began to feel myself. He offered a tour of the building. The kitchen, set up for catering. The lounge was for greeting guests. Two other rooms for entertaining club members. Everything was luxurious. There was a door off of the lounge. He said it was the security room with monitors. He explained all of the common rooms had cameras along with outside surveillance. He told me that none of the bedrooms or bathrooms had cameras.

The second and third floors were bedrooms. Four on each floor with en suite bathrooms. Again, luxury. He explained that the bedrooms were mostly used for overnight guests when they had club events, adding that most meetings with clients would take place at hotels or client's residents. I was visibly relieved that it was not a brothel as I had been imagining. We then got in the elevator to the basement. He said the basements were for the staff only. A large staff lounge and changing room. Laundry room. We then walked down a hallway towards what he called the office. When we entered the office I was surprised that it was multiple rooms. A waiting area with couch and chairs. An office that he just referred to as booking. We then entered a larger room with two large desks and chairs. He said this his and his partner's office. I had been unaware that he had a partner, Rachel never mentioned this. He told me to have a seat while he entered a door off of his office. I heard him talking and then silence.

I sat there a few minutes until he and a woman came through the door. He introduced her as his partner, Pamela. I stood to greet her, towering over her. She might have been 5', maximum. Short, slender, large breasts, hair colored red, dressed in a business skirt suit. Very attractive but obviously older. Like George, I would put her age in her 60s.

We shook hands but she was very slow to release my hand. Her other hand rising up my arm, feeling my muscles. She smiled and said to George that he was right, I would be very popular. I blushed. She laughed loudly and let my hand go. She turned back to the doorway and walked through, George gesturing that I should follow. It was brightly lit room, setup similar to a hotel room. Small couch and two chairs, a large bed in the back half of the room. She and George sat in the chairs, pointing to the couch for me.

Pamela began by telling me that she and George were partners and had run the club for the past 32 years. She talked about their clientele, which Rachel had told us about previously. She and George began asking me questions about myself, my family, my past, my school, my future. Nothing sexual. It felt like a scholarship interview, honestly. George then asked me what I was comfortable with. I had no idea what he meant at first. Then it dawned on me. I told them that Ana and I were open to working as a couple and that we were very open. I began to fill them in on my sexual past.

Pamela interrupted to say that they mean specific acts and began to ask me acts. Nude massage. Yes. Fingering. Yes. Oral on a woman. Yes. Oral on a man. Hesitated, but I replied yes. Oral on a man with no condom to completion and swallowing. Holy fuck. This shit is real now. Yes. Sex with a woman with a condom. Yes. Top sex with a man with a condom. Yes. Bottom sex with a man with a condom. No. George said that was a pity. Sex with a transgender woman with a condom. Yes. Sex with a transgender man with a condom. Yes. Then I was hit with a sledgehammer. Sex without a condom with current medical testing. I never thought that would be a thing. I instantly said no. I set a mental reminder to ask Rachel about this.

I did not use condoms with Ana but I had with all my other partners. They asked me if I had done anal much. I told them I had. Pamela said I would need to be tested before I did anal with a woman to be sure that I would not injure her. They asked about fetishes. I said no to heavy pain, shit, and blood. A lot of the fetishes I had no idea were a thing. But if someone wanted to pay me to wear a diaper then I was fine with that. George let me know that if a client requested any type of outfit the client was responsible for paying me for it, regardless of whether I already owned the outfit. They also mentioned that the charge to the client would be many times more than the actual cost. This made me laugh, it was like the cheap wine that restaurants would charge $50 for.

At this point the interview was interesting and I was pretty relaxed. I have always enjoyed talking about sex. George then told me to get undressed. Well, I was relaxed. I stood but I wasn't sure whether to make it sexy or just get nude. I decided to just get nude. Odd situation but I was not uncomfortable. Standing nude in front of two people in their 60s, evaluating my body. Pamela said that I looked perfect and had a wonderful cock. George nodded and said maybe too big. He asked me to lift my cock and then lift my balls. Then he asked me to turn. Pamela told me to bend and spread my cheeks. I felt like livestock but not embarrassed. I was getting turned on. George asked me to sit and get myself hard.

I closed my eyes and began stroking myself. I thought about Rachel earlier that afternoon. I felt myself growing. I began to feel very proud of my cock. I wanted to impress Pamela and George. I was close to completely hard. George asked me if me if I wanted some lube to get myself completely hard. I told him yes and saw him go to the nightstand. He handed me a bottle and I poured some on. This let me get that extra bit of hardness. I told them I was completely hard. Pamela seemed pleased but George just said they needed to measure me. He came next to me and pulled out a cloth measuring tape. He took my cock in his hand and stroked quickly and firmly. Then he measured me. 8 and 1/8th inches.

He said they would advertise 9 inches. He stroked me again and wrapped the tape around me. 7 and 1/4th. He suggested advertising 7 inches for the circumference. I asked why advertise smaller. He said larger circumference might scare people off. This was all new to me. George stayed on the couch next to me and kept stroking. He asked how often I could cum. I told him many times. He laughed and said he wished he was young again. Pamela asked me if I had ever used medicine or supplements, like Viagra, DHEA, or ginseng. I said no. She said I should look into so there would never be performance issues. The entire time George kept stroking me. He asked if it felt good. I said it did. He asked if I was close to cumming. I said no. He let go and Pamela told me to make myself cum.

I closed my eyes and started jerking off quickly. They told me to open my eyes. They kept asking random questions, some sexual, some not. They asked some of the same questions from earlier. It was distracting. As if reading my mind, Pamela said that I needed to be able to cum even if I was not turned on or if my attention was elsewhere. I calmed myself down so I could focus on both the conversation and on cumming. This was difficult but a few minutes later I told them I was going to cum. My load shot out, high, across my chest, over my shoulder, landing on the couch. Several more shots landed on my stomach. Fuck, I needed that after Rachel's teasing that afternoon. Pamela smiled and said to do it again.

Forty-five minutes later I shot my fourth load. They seemed impressed but still recommended that I look into supplements.

George asked me if I was free on Sunday. I let him know that I was. He said he had a client for me, her name was Rebekkah and had been a long time member of the club. I would meet her at her house. I reminded them that they had not interviewed Ana yet. How would they book us without talking with her. Pamela said that the appointment was for me alone. I explained that they were mistaken, Ana and I were a package only. George said that would not be possible. Us being a couple would be an option for clients but we would need to be available for solos as well. I said that I needed to talk with Ana about this. Pamela could see that I was upset about this. It was not what we had discussed with Rachel. It was not what Ana and I were expecting. I was feeling pressured to decide now. I was also desperate for the income.

Pamela showed me to the shower and told me to take my time. I took a long shower and got dressed. When I came back into the room, Pamela was sitting on the couch, waiting for me. She motioned for me to sit next to her. She said they were eager to work with me. They wanted me to be comfortable but also needed the flexibility of booking us individually. I reiterated that I would need to discuss it with Ana.

We stood up and made our way back through the basement. The booking office was occupied. A pretty woman was seated at the desk. She smiled and waved when I walked by. The staff room had several women in it as well. A quick glance and I could see they were all gorgeous. Back on the first floor and I heard voices from several directions. Pamela said they were having a club event that night and the staff was getting ready. Back into the greeting room and there were two women and a man seated. Everyone was beautiful. When were at the main door, Pamela said that it was clear that I would fit in well with the other staff.

Once I stepped outside, I turned on my phone. I had no idea what time it was. 7:15pm. Damn, I had been there for over three hours. Checked my messages and I had one from Ana, wishing me luck and letting me know that she took the closing shift to make bit more money and would not be home until after midnight. I had a message from my boss at my internship to take tomorrow off to be sure that I was not sick. I also had four messages from Rachel. Telling me that she just finished with her date. Asking me how my interview went. Asking me to call her. Asking if I wanted to grab a drink. As I was reading her messages Rachel messaged me again, asking me again to call her. I clicked on her contact and called her. She said that she wanted to have some drinks and go over the interview. I really did not feel like it, I wanted to go home and think. I agreed to meet because I was feeling like I owed her, for dinner and hooking us up with the interviews. She said she would meet me at the bar in the Plaza hotel since that was where her date had been and it was only two blocks away for me.

I got to the bar at the same time as a large group of businessmen. I saw Rachel and she had a glass of wine waiting for me. Unfortunately, the businessmen were right next to our table. We started to chat but the guys were loud and I did not feel comfortable talking about the interview. Two of the guys were also eye-fucking Rachel. It was an uncomfortable situation. After one of them bumped into my chair for the third time, Rachel saw that I was getting pissed. She said that she still had the room from the client and suggested we go drink from the mini bar and talk in the room. When we got to the room she told me to make us drinks and that she was going to hop into the shower. I pounded two drinks while she was in the shower. I relaxed on the couch and my mood improved.

She came out with her hair wrapped in a towel, wearing a tank top and panties. When she saw me on the couch, she made a face and told me to sit on the bed because she had fucked her client on the couch. I laughed and said I was tired of couches since that was wear Pamela and George had me jerk off. She asked me to tell her about the interview, asking questions and for details while I did. I told her everything. I explained that I was hesitant due to having to do solos. She apologized about the confusion, she said she thought Ana and I would be able to do couples only. She asked me if I thought I would do solos. I told her that I would but only if Ana was comfortable. I told her it was all about money for me. She agreed, she did it for the money. Any fun that she had was just a bonus. I told her about Rebekkah and she said that they must really want me to work. She explained that Rebekkah was definitely a VIP. Longtime member, incredibly rich, huge tipper, low maintenance client. Rebekkah was a widow in her late fifties. She usually just liked to do mutual oral and was well known for tipping. This sounded great to me.

By now I had had four drinks in the room along with the glass of wine at the bar. I wanted to stretch out while we chatted. I lay back on the pillow. There was a lump. I reached under and pulled a Hitachi wand. Rachel started laughing and blushed. She looked adorable blushing. She explained that her client today was what she considered a dud. He was a nice guy in his late sixties. One of her regulars. A good guy but was not talented sexually. He would eat her out but not long enough to get her off. Then he was a challenge to get hard enough to fuck. Once he was able to get it up he would cum in a couple of minutes. She said she never had an orgasm with him. But had to fake it the entire time. She said she always used her wand after he left.

Playfully I sniffed the wand. She blushed again and claimed she did not use it yet. Then she jumped on me to take it away. We were laughing and giggling while wrestling over the vibrator. At that moment one of our fingers turned the vibrator on and set us off laughing again. I fell on my back and she fell on top of me. It felt great to be laughing and it felt great to have her body against mine. We calmed down but she did not get off of me yet. I pulled the vibrator up and shut it off. I said that I had never seen one so powerful before. She said that at night it sounded like Ana did not need one. She said it playfully. It turned me on though. I had never seen her in a playful mood before. She was always friendly but we had never been silly together. I realized that I was getting hard and that she could definitely feel my cock. I sat up and slid back.

She got a bit serious and asked me how many times George and Pamela had me jerk off. I told her four times. She asked if that was the most I could do. I told her no but they did not ask for more. She looking pensive for a moment and said that Ana was lucky to have me. I laughed and said I was lucky to have her and that it was not all about sex for us. She clarified that she did not mean just about sex. She said she watched us together and saw how happy we were. I asked about her dating life. She laughed and said guys did not want to date her, especially with her job. Five minutes ago she looked so happy, giggling. Now she looked like she was going to cry. I gave her a hug. It was the most platonic hug I could manage considering I was hard still from when she was laying on me. We stayed like this for several minutes. Finally her head popped out, eyes a bit red. She said lets get drunk and jumped up. She was heading back to the mini bar and turned back to ask me what I wanted to drink. just as she did, I was adjusting my cock. She grinned at me and walked back to me. She had devilish look on her face and said she was bored with the mini bar and wanted to order wine from room service. She told me to call down and order three of the most expensive red wines. She said it would all go on her clients tab.

While I was on the phone she laid on the bed and stretched out. Her tiny body was so sexy. My cock was painfully hard. When I hung up the phone she rolled over towards me, eye level with my crotch. She asked if I was wearing underwear. I said I was, I was wearing the ones she had chosen for my interview. She laughed and said I should take my pants off so I would be comfortable. I knew it was a stupid idea but at the moment I thought she was a genius. She said I should strip for her, like she was my client. She turned on music and sat back against the headboard. I did what I thought was a sexy dance and stripped down to my underwear. She told me no, it is not sexy enough, do it again. I laughed but she said that she was serious. She said it is part of my new job. I dressed again and set my mind on doing a better job. I moved my hips slowly, trying to be sexy for her. Unbuttoning my shirt, teasing her with glimpses of me.

I was sure that I looked hot. Once I was down to my underwear again, I turned and pulled them down a bit, showing off my ass. When I turned back to face her I could not read her mood. She said I did better but needed to practice and to get dressed again. For the third time I began to strip, trying to remember every hot R&B video and steal their moves. Just as I was pulling my pants down there was a knock at the door. I threw my shirt on and answered. It was room service with our wine. When I came back I figured dancing was done but she told me to strip again for her and to use the wine bottle as a prop. She scooted to the end of the bed and was sitting there with her legs hanging over. She told me that she wanted me to convince her to fuck me just with the dance.

I was feeling a bit ridiculous at this point. I had stripped for her three times already. I just thought fuck it and started an over the top dance. I stood between her legs, slowly stripping, rolling my hips, flexing my muscles, holding the wine bottle like it was my cock. I turned my back to her and was rubbing my ass against her crotch. While I was turned I opened the wine. When I turned back I took her hair in my free hand and tilted her head back like I was going to kiss her before pulling back away from her. She moved forward and slid off the bed, down to her knees. I let my pants drop and slid my briefs down to show the base of my cock. I pushed her lower between my legs and tilted her head back. I could see in her eyes how turned on she was. I brought the mouth of the wine bottle to her lips and she took a big sip. I started to slide my underwear lower, half of my cock was showing. I was ready to put it in her mouth. She looked up at me and had the sexiest smile. Then she sat up and said that I did a great job, that I should dance like that for clients. Fuck.