Putting Myself Through College

The next few weeks went by uneventfully; I settled into a nice routine with my new landlords Greg & Nina and continued to work mostly hourly assignments for Kevin. I had begun speaking to my parents more, and Nina even spoke to them once, assuring them that I was welcome to keep renting from them until I graduated from college. All seemed to be coming together nicely, and I looked forward to a rewarding summer.

I received a call from Kevin early one morning in the middle of the week, it was just after 6am, so I thought that there must be an emergency of some kind. Kevin apologized immediately for calling so early, I assured him that his call had not disturbed Nina or Greg. I have a real winner for you he told me, an assignment that will pay really big bucks if you want it. I immediately asked for the details and he told me the story of Jim and Lonnie.

Jim and Lonnie were two older gentlemen who had been long time partners, and both shared a fancy for young college guys. Jim's business had just took off after many years of struggling, and now Jim and Lonnie were spending their money like there was no tomorrow. I could tell by this that Kevin was taking them for a lot, my cut would be nice, but I had the suspicion that Kevin was about to make more off of this assignment then I would. The assignment was for me to accompany Jim and Lonnie on a road trip, a vacation that would last for about five days, and my fee would be $ 15,000. I accepted it, but quickly realized Kevin must have charged them around $ 40 to $ 50K for my services, he loved to take advantage of rich old queens.

I made arrangements with Kevin, I would leave the every next day. I informed Greg & Nina that I would be gone for about a week, while they could not wait to hear about my adventure when I returned, they both told me that they would miss me in their own way. Greg simply grabbed my ass, well he first stuck his hand down the back of my pants to squeeze me, and told me that he would miss fucking me. Nina said that she would miss the company and all of the fun that the three of us always had.

The following morning Kevin picked me up and drove me to his office, I had packed lightly as Kevin had instructed. Just after 10am, Jim and Lonnie arrived, they were driving a large convertible Cadillac. Kevin invited us all into his office, where we were all introduced, Jim and Lonnie were very friendly. Kevin spoke to them about the arrangement and when I was due back, they agreed and we were off.

Jim and Lonnie were both in their early 50's, Jim was around 5'8" and must have weighed over 250 pounds. Jim was heavy set in his appearance, but very gentle in his actions. Lonnie was slightly taller, around 5'10", and was in better shape than Jim weighing I would say about 30 pounds less. The first couple of hours we just talked and listened to their oldies station. Jim told me how he and Lonnie meant when they were both in college; they attended a southern university, so they always had to be very discreet.

I asked what their plans were for the week, and they said just to drive around and stop where ever they felt the urge. Jim was doing the driving that morning, until we stopped for lunch. They grabbed sandwiches from a small deli just off the interstate, and then we drove a short distance away to a rest area. The rest area was remote, with little traffic that time a day. We parked the car and instead of going to the picnic area, we all walked a good distance up a wooded trail, until we were far from anyone else. The three of us stopped at a grassy clearing and sat down on the ground and ate our lunch. I was hungry and so was Lonnie as we finished in no time, Jim seemed to be relaxing and eating at a leisurely pace.

Lonnie moved closer to me, and dropped his hand in my lap. He started to feel me up, and suddenly I became erect, this made him smile and laugh, as it was the response he was looking for. Lonnie started to undo my shorts, and pulled them down to my knees. He motioned for me to lie back on the ground, and he engulfed my cock into his mouth. Lonnie was excellent at giving oral, as he worked my cock in and out of his mouth, taking his time to use his tongue on all of my important spots. Eventually my cock came out of his mouth and he sucked my balls into his mouth at the same time. This felt incredible as he knew just what to do, so it felt good and did not hurt (my testicles can be sensitive at times when sucked). Lonnie continued to work my groin area, eventually moving lower and penetrating my ass with his tongue. Lonnie ate my ass for a good while; we were eventually interrupted by Jim who told us that he thought someone was coming. We quickly corrected ourselves, Lonnie moved away from me, and I pulled my shorts back up. Soon a family appeared who was hiking up the trail. We did not make eye contract, just gathered our trash and started to walk back to their car.

I was very disappointed to say that least, I had a raging hard on and was almost there, when we were so rudely interrupted. Lonnie drove after lunch, and as soon as we had driven just out of the rest area parking lot, we all made a joke about almost getting caught. We were only a few miles done the road, when Jim climbed into the back seat with me, and told me to unzip my pants. Well we were in a convertible, and anyone passing us by could see everything. Jim insisted, so I unzipped and pulled out my cock, just barely moving my shorts down. Jim immediately leaned over and buried his face in my lap, taking my cock down into his throat in one action. It did not take long, as I came down his throat with a thunderous explosion. Jim swallowed it all, and then told me how he hated to see my erection go to waste. I had not seen anyone pass us while this was taking place, though I was blind to the world while getting my penis sucked. Lonnie had sped up so that he kept our distance from other vehicles. I then sat back and listened to Lonnie and Jim discuss the taste of my cock, balls, ass and cum. It was like I was not even there, they were such teases.

We pulled off the interstate just around dinnertime and found an old motel. Jim went inside and rented a room for the night as Lonnie and I sat in the car. The motel was an old one, one of those relics from a bygone era; we got the room at the very end. When we parked I looked around and saw that there were few if any other discernable guests. The room was want could be expected, two double beds, an old TV, one dresser and a small bathroom. The popcorn ceiling had seen better days, and there were a few water stains, the only thing missing for the most part were bugs of some sort. Thankfully the owners thought enough of the place to keep it clean, at least to that level. Since the sign out front advertised hourly rates, I guess you can complete the picture of the entire place.

As this was their vacation and my assignment, I did not question the locale, this was definitely road trip material. Lonnie asked what we all wanted for dinner, and headed out to grab some fast food. As soon as he left, Jim just took his clothes off with no production. He asked me if I wanted to wash up before dinner, I understood what he meant, so I removed my clothes as well. We went into the bathroom and Jim washed his hands. I followed his lead, and when I bent over the sink, Jim fell to the floor and started to assault my ass with his tongue. I had never preferred to use my tongue on a mans ass, but Jim and Lonnie seemed to love it, so I figured if this is how they want to play, I would go with it over the trip.

Jim had my ass cheeks spread as far apart as they could go, as his tongue was inside of me now, darting all around. Jim reached around and stroked me while he did this, and soon I was coming on the sink. He knew that I had finished, when my legs had stopped buckling, it was then that Jim stood up right behind me. Jim kept me pushed forward and lined his cock up with mine. I had not seen it hard yet, just a quick glimpse when he had walked into the bathroom. I felt it enter, I could tell that it was not very large at all, most likely not even as big as mine. Jim pushed forward with all his might, time and again, he lasted a few minutes, and then came with a loud grunt. Jim then pulled out and dropped to his knees again and cleaned out my ass with his tongue.

We walked out into the main room still naked, well I guess you should call it that, only two rooms between that room and the bathroom. Lonnie arrived shortly thereafter with our food, Jim greeted him with a passionate kiss, their tongues played for a while and then Lonnie said that he could taste Jim & my encounter. Lonnie shed his clothes too, and then we all ate. TV followed dinner, as the two of them watched tabloid news shows for the next hour. They kept asking me for my opinion of some of the stories, but I really did not have time to keep up with such crap.

They finally turned the TV off and we all laid back on the one bed and talked. I found out more about their relationship and their lives growing up. Jim had never come out of the closet to anyone, it was just obvious to anyone who met him that he was gay. Lonnie had tried hard to act straight his entire life until he went to college, both he and Jim chose the school they did, due to the distance it was from their home towns. Lonnie told me that he fell in love with Jim the day they meant, as he found that he could be himself with Jim for the first time in his life. Jim jumped in and said how he had just always lived his life how he wanted it, he just did not openly express his sexuality to anyone. This led of course to a discussion about me, and when did I first know. When I told them that I did not know until I took the job, this made their eyes pop out of their heads. They both said that they wished it had been them and not Mr. Deverson who had the honor of taking my virginity.

By this time in the conversation, all three of us were hard, and I could see that neither of them was particularly large, both right around my size or smaller. They asked what I was willing to do, as they both had a few fantasies. I told them some of the things that I had done in the past and they both became excited by this. We were soon joined in a three-way, Jim's cock in my mouth and Lonnie's in my ass. Our sex was very enjoyable, and neither seemed rushed, nor did they seem to want to exude any sort of dominance over me. This allowed me to feel Lonnie pushing in and out of me, yet while he did this, I was still in enough control to focus on pleasing Jim with my mouth. Lonnie shot his sperm into my ass, then pulled out and just sat back to relax. Jim and I then rearranged, into more of a 69 position, where Jim tongued my ass for Lonnie's cum and I continued to work his cock in and out of my mouth.

Jim stopped working on my ass after a while and I shifted positions once again, this time moving around so that I was between his legs. I took his small cock into the back of my mouth, and tried my best to concentrate, before I knew it (and very much to my delight) I was actually working his cock into my throat. Wow I was actually deep throating him. Jim came without warning and I started to choke a little. I had to pull him almost all the way out of my mouth to catch my breath, but I did not let any of my reward escape my hungry mouth. Lonnie applauded the show, and Jim just laid there with a huge smile on his face.

My cock was painfully hard still, and to my rescue came Lonnie. He took me into his mouth and sucked on me for a while. He brought me to the edge several times, but did not let me finish, oh the wisdom of the elders. Jim soon joined him and I looked down to see them passing my cock back and forth between them. I could take it no longer and let my happiness cum out of me. They shared it, and soon we were all just snuggled up with one another, regaining our strength. Our night was not over just yet, as just before we all went to bed, Lonnie went down on me out of nowhere. Jim stood up, just off to my side of the bed, and stuck his cock in the direction of my mouth. I immediately accepted his offer and invited his cock into my mouth with a lick of my lips. This had quite the effect on Jim, I finished his rather quickly. Lonnie worked me very well during this time. Once Jim had finished, Lonnie maneuvered my body, so that he could fuck me. He entered me by sticking his entire cock up my ass with one push. Thankfully I was still loose from earlier, plus he was not that big. He finished me with his hands, then finished his pleasure inside my ass. Lonnie, scooped up my cum into his fingers, then fed it into his hungry mouth. Wow these two men were showing me a great time. We all went to sleep then, I had one bed to myself, as the couple shared the other.

I awoke the next morning to the sounds of Lonnie fucking Jim, I looked over and saw Jim's legs over Lonnie's shoulders, and Lonnie was fucking him as hard as he could. I went into the bathroom to clean up, and let them enjoy some alone time. I masturbated in the shower, listening to the two of them fucking in the other room, I guess you can say I left the bathroom door open on purpose.

We pulled away from the motel around 9 that morning, and headed back onto the interstate. Lonnie drove, and the three of us talked some more. I asked them if they were each other's firsts, as I had become more comfortable around them, usually a model would not ask clients personal questions. Lonnie said no that he had fucked two different girls in high school, one on prom night, the other late in his senior year, to try had prove his manhood to the other guys. He told me that if they had found out he preferred men, they most likely would have killed him. Jim told me that his first time was when he was in high school as well. He said that he had skipped school one day and that a friend of his fathers caught him. Jim said that the man suspected Jim's sexuality, and Jim did not deny it. The man asked Jim to blow him to keep everything quiet, Jim said that he did more than that, he in fact asked the man to fuck him. Jim said that his father's friend helped him out a few more times, but later became paranoid that they would be discovered, and told Jim to stay away from him.

We had skipped breakfast that day, so we pulled off the interstate and had a real nice lunch at a mid-priced restaurant. During lunch, Jim said that he was tired of driving for the day, so when we finished eating we found a very nice hotel near by.

Our room was on the sixth floor and came with two king size beds, a large screen television, a wet bar and a very large bathroom with a whirlpool tub. We relaxed for a while, letting our stomachs settle, watching some TV. The hotel had a very nice menu, and Lonnie suggested that we eat in that night, we all agreed despite food being the furthest thing from our minds at that moment.

I was really enjoying this assignment, it was not like work at all, it truly was a vacation for me. Everyone was relaxed, no one had to get to the sex right away, because the clock was ticking. The fact that Jim and Lonnie allowed me to get to know both of them in a personal way was a real positive as well, it helped me become more comfortable with them, and in a way opened up my mind to new suggestions.

By mid-afternoon, we all found ourselves in the whirlpool tub. Jim was bent over the side of the tub, my cock was in his ass, and Lonnie's was in mine. I loved being in the middle of an anal sandwich, as long as everyone was the right size and allowing it to be enjoyable for me. Jim & Lonnie were treating me like an old friend, not a hired piece of ass. He continued fucking each other in unison, until both Lonnie and I had finished. Jim brought himself off with his hand. That is all we did that afternoon, as we cleaned up and then went for a walk around the area. Jim and Lonnie did a little shopping, we only went a few blocks from the hotel, as there was not much to do in that location. We continued to talk and learn more about one another. I told them about my current living situation, and how it was working out perfectly for all involved.

When we returned to our room, Lonnie told us to order dinner, and that he would be back in a little bit. He must have to Jim where he was going, as Jim giggled, then looked at me and smiled. I inquired, but was told it was a surprise. Lonnie returned before our meals had arrived, and had a large brown paper bag. Since no one made an attempt to stop me, I looked in the bag when Lonnie put it down on the bed near me. Lonnie had went to an adult bookstore or an adult store of sorts, he returned with a large bottle of lube, several butt plugs and an oversized gay magazine featuring several group sex scenes. He asked if I liked what I had found, and I said yes. I did not get a chance to flip through the pages as we heard a knock at the door. I put everything away, as Jim opened the door. Our food had arrived, and Lonnie tipped the waiter. None of us ordered a large meal, we all ate light, I guess you can say we did not want to fill ourselves up with food, no we were all hungry for something else.

Later that night we all got undressed and formed a circle on one of the beds, we each took one of the others cocks into our mouths, and proceeded to suck each other off, taking our own sweet time about it. Eventually we moved into other positions, and I found myself servicing both Jim and Lonnie. We had all cum several times, before Lonnie suggested getting a porno on the TV. They had no gay porn, so instead we settled for looking through the pages of the large magazine. The pictorials all featured group sex, with one young man always at the center of the action. Some were a bit more extreme than the others, including one where a young man had two cocks in his ass, and two in his mouth at the same time, not sure how they got everyone to "fit" in that picture (in more ways than one). Looking through the magazine brought all our cocks back to life, despite the extensive use that they had received that evening.

Lonnie pointed a picture and asked if I minded trying that, it turned out to be a picture with a young man sandwiched between two guys, who were both in him at the same time. Under any other circumstances I would not have tried, my ass was too small I thought, but these guys had me turned on and neither had a cock that scared me by its size. Jim lubed both of them up, while Lonnie worked a couple of lube covered fingers into me. I was so excited about trying this, it would go beyond anything I had tried before.

Jim laid down, and I allowed him to enter me first, then I moved off of him and allowed Lonnie to enter me. I next moved back onto Jim, who held very still. Lonnie then gently maneuvered himself into me over the next five minutes. They both keep on moving in and out, trying to align themselves in just such a way that they would both fit. Finally with some discomfort, but no real pain, they had made it. The feeling was so overwhelming, that as soon as they started to fuck me in unison, the feel of two cocks at once made me cum without anyone making contact with my cock. They lasted only a little longer, but my god if you ever get the opportunity, go for it I say.

We all feel into a heap, and that is were we slept that night. I slept wonderfully, thankfully I was sufficiently tired enough that the empty feeling in my ass, did not keep me awake. Funny thing, the next morning when we left, I noticed the one bed was still as we found it, the other, well that was another story.

The next morning, as we had all grown much more comfortable with each other over the last few days, Jim suggested that we do something naughty during our car ride. The butt plugs that Lonnie had purchased were used that morning, each of us inserted one before dressing. The feel of it that I received whenever I moved or shifted during the car ride was fantastic.