College Days as Gay Escort

[Toddxxx]

Hi! I'm Seth. No, I'm not a slut, but as the title of this story indicates I was a gay "escort" during my senior year in college. Let me explain before you pass judgment. There are times, maybe also for you too, when necessity forces you to do stuff you wouldn't otherwise do. In college I was on a three-quarters scholarship based on financial need. My Mom was a waitress at IHOP, a single Mom with two younger kids at home. I worked a part time, minimum wage job throughout college to pay for the other quarter of my college expenses, but as tuition at school rose each year my meager salary just couldn't keep up and I had to consider dropping one year before earning my degree.

Some more background. I am gay. Came out in high school. My Mom was upset, but said she always suspected and has been very supportive. I've had a series of boyfriends, but nothing long-term. I like sex a lot, but certainly am not promiscuous. I sleep only with guys I know and like.

Now back to my college financial problems. One day in the cafeteria Mike, my sophomore year boyfriend, and still a good friend, sat down next to me. Hey. What's up with you? You seem so gloomy lately."

"Money! I don't make enough to pay my bills. The fucking legislature keeps upping tuition. I may have to drop out of school for a year to earn more money."

"Shit, you have only two semesters to graduation. Can't you take out a loan or something?" he suggested.

"Yeah, and with what co-lateral? I'm already on scholarship, don't qualify for a Pell Grant and my Mom is having problems just paying her monthly mortgage. What else is there?"

After a long pause Mike said, "There is another option."

"Tell me. I'll take it!"

"I know of a big bucks guy who signs up hot college gay boys to be escorts for some high paying customers. I hear you can make up to $300 a night maybe", Mike whispered.

"Have you done that?' I asked.

"Nah, I don't need the cash that bad now, but I know a guy who did. He said the money was great and the men he met were all okay", he admitted.

"I can't do that Mike. Call boy? No way, but thanks for listening," I replied.

When my college bills came due I felt pretty desperate. I called Mike and asked for the name and number of his "big bucks guy". He said he'll try to get it for me which he did the following day. "Here's his cell number. His name is Benjamin. I don't his last name", Mike said. I grimaced and thanked him. "Good luck, man", Mike added.

It took me a few days to get enough courage to call. Benjamin asked a few basic questions - how I had heard of his business, my age, height, weight, sexual orientation, etc. - then asked me to meet him the next morning for an interview. When I asked him for the address of his office he said abruptly, "No office. All my business is done on-line or by phone. See you at 10 at the Java Joe on University Street."

What the hell was I getting into?

 

[IowaGuy]

I can't wait for the second installment.

 

[lets-rock-this]

Nice start to the story bro.

 

[Toddxxx]

When I got to the coffee shop there were only a few people there. They were students mostly except for one guy who looked like a model for J. Crew - Docker's, colored T-shirt and a blue sports jacket. He was busy on his cell, but when he finally noticed me he got up and asked, "Are you Seth?" I nodded yes. He ordered two coffees and ushered me to a corner table away from anyone else.

"Hey! Good to meet you Seth. I'm Benjamin. I think I got your basics - gay college senior who needs money - right? And, you heard about my business from a friend who knows a boy who worked for me."

"Yes sir", I answered.

"First, do you have any questions?"

Bluntly I asked, "How much do you pay me for having sex with your men?"

"Well, get this straight. I don't pay you anything for having sex. I operate an escort service. I introduce young men to my clients. What they do together is up to them to decide, not me."

Okay. I get it. How much....how much for a date then?", I said with a smirk.

"I like guys who are direct. First time $150. If it works out well it goes higher after that. Besides, my clients are all very well heeled and generous tipping is typical if they liked your company."

"Sounds okay to me", I replied.

Despite Benjamin's disclaimer about him not paying for sex, he asked about my sexual practices and experiences, my likes and dislikes and even some kinky stuff. I answered candidly and then he said if I am going to work for him he will need some photographs to show to his clients. I hesitated and he said,"No photos, no deal." Reluctantly, I agreed.

We drove in his sporty Saab to a small motel in a seedy part of town. Nice office I thought, wondering again what I was getting into with this guy. A motel room for Christ's sake. Was he looking to audition his cock in my ass as part of the interview? He took some photos of me standing and then sitting on the bed. "Now some candid camera shots. Okay, take off your clothes", he ordered.

"What! You want pictures of me naked?"

"My clients want to see more than your pretty face."

"And then what do you do with the photos?"

"Your personal portfolio gets posted on my secure, subscriber-only website. Don't worry. The pictures cannot be downloaded."

"Yeah. I bet. So can I check out your clients too? Don't want to bed down with some fat old fart you know", I inquired sarcastically.

"Cut the crap Seth! Anonymity is critical for my clients. They are all professional men and most are married. I'm paid to to avoid any possibility of a scandal. No one will see your portfolio but my clients and they sure don't want any problems. Now strip if you want the job."

I pulled off my shirt and dropped my pants. I was wearing a red Jockey bikini to which Benjamin exclaimed, "Nice! Sexy underwear is a plus." He took a variety of shots of me posing in my undies. "Good! Now shuck the underwear", which I did. "Oh, great! Shaved and smooth is a real big plus." He took nude pictures of me in various poses - leaning against the wall, in the bathroom, sitting open-legged in a chair and lying on the bed both supine and prone. He also took some close-ups of my genitalia and my butt cheeks spread wide. "Seth, I know my clients are going to love you! And you will like their money."

I dressed quickly. Benjamin drove me back to campus. "When will I hear from you?", I asked.

"It might take a week or two, maybe sooner. I got your cell. I'll call you."

 

[rain09]

can't wait to see how this develops- it's great so far

 

[hardreader]

Hey, Todd, life is always good when you're writing. Good to see you back on the boards. I'm ready for Seth to get a workout!

 

[ShihTzuTylenol]

hmmmm generous tippers? maybe I have missed my calling HA!

keep the pages coming Todd

 

[Toddxxx]

Ten days passed before Benjamin finally called. "How does this Thursday night work for you?” he inquired.

"It's good. What time and where?” I asked, trying not to sound too eager.

"Nine o'clock at the Marriott. When he checks in he will call me with his room number which I'll pass on to you. Go straight to the room. Do not stop at the front desk,” and he hung up before I could ask him anything else.

I was anxious all day Thursday. Benjamin called with the room number, Suite 920. I asked him about the client but all he would tell me was that he was one of his regulars and the boys liked him. I showered and brushed my teeth. I decided to wear that same red bikini that I wore for my interview photo shoot; the one Benjamin said was "a plus". I got to the hotel a bit early so waited until nine to knock on the door of Suite 920.

"Well, you must be Seth. Come in. Can I get you something to drink from the mini-bar?"

"No sir,” I replied.

"Skip the sir. Call me Terry."

"Yes sir....I mean Terry,” I said with an embarrassed smile.

Terry looked to be in his late forties, maybe fifty. He was handsome, trim and soft spoken, someone who had his hair cut weekly whether it needed it or not. He was wearing only a white undershirt and black silk boxers. He invited me to sit down while he poured himself some scotch. He engaged me in small talk about college life for a few minutes while he sipped his drink.

"I loved your pictures,” he offered and, fingering my shirt, added with a knowing smile, "and I'd like to see a little more of you, in the flesh so to speak." I started to unbutton my shirt. "No. Let me do that,” he said and proceeded to undo each button slowly. I noticed that his cock was beginning to tent his boxers. He began rubbing his hands over my bare chest.

"Relax Seth. I don't bite." He then unbuckled my belt. I stood up, kicked off my sandals and let my pants drop to the floor. My bulging crotch was at his eye level. He cupped my balls softly with one hand. "Now that's nice,” he whispered.

Terry stood, pulled me toward him and gently kissed me. Earlier I had worried that maybe I couldn't even mount a hard-on in a paid for sex situation, but with the feel of his hard cock and silky underwear pressing against me I sprouted a major erection. I returned his initial kiss. He was hot for sure, me too. Our tongues sensuously explored each other’s mouths. "You are one very hot boy,” he muttered between breaths.

I had always thought that my partner's sexual wants at the moment were signaled by where he put his hands upon initial encounter. Terry's hands went straight for my ass which he massaged softly as we continued kissing. I was turned on, no doubt about it. I wanted him!

Terry took my hand and led me to the bed. Still in our underwear, he laid on top of me, shifting his pelvis in barely perceptible slow movement against mine. I loved that feeling. Terry sure knew what he was doing. After a few minutes we exchanged positions, continuing our hot pelvic engagement while kissing passionately. Terry's hard cock was now protruding through the fly of his boxers and I wanted it. I started on his neck, then his nipples, kissing and sucking as I descended toward his raging cock. I pulled off his boxers. His hard cock was no more than six inches with an upward curve. His pubes were closely trimmed and his balls smooth, maybe shaved. He spread his legs. I started working my tongue on that sensitive spot at the base of his balls. He moaned when I took his balls one at a time into my mouth and gently massaged them with my tongue. I could tell that he loved it when I ran my tongue repeatedly up and down the underside of his beautiful cock. I toyed with his glans before getting down to some hard cock sucking.

After about five minutes of me giving him some incredible head, Terry pulled me off him. He reached into the nightstand for a condom and rolled it over his erection. He extracted my cock from my bikini and slipped it off. He raised my butt, spread my cheeks and rimmed me for a short while before positioning his cock on my hole. With some gentle pressure he penetrated me easily, pushed me down and commenced a long, slow fuck. He paused periodically. I knew that he didn't want to cum too soon, sort of like edging while enjoying the pleasures my tight ass. I sure wasn't about to complain. I loved the sensation of every stroke of his curved cock. I don't know how many minutes this went on, but when he pulled me up on my knees and began some hard fucking I had a terrific orgasm, shooting loads of cum onto the sheets. Terry came with a loud groan soon afterwards and collapsed on top of me. He kissed the side of my neck until his erection subsided and his cock slid out.

We lay there for a few minutes catching our breath. "That was fantastic,” Terry whispered. "You are one fucking hot boy!"

I got dressed and was about to leave when Terry said, "Wait!" He found his wallet. "Here. Something extra for an incredible time. Thanks". He gave me two fifty dollar bills. "I'd like to see you again, okay."

"Yes sir. Any time,” I answered and left.

 

[DonQuixote]

Hi, Todd.
I haven't hit the main story listings for a few, missed your latest entry till this morning. Very nice installment. Unfortunate(?) to find oneself in need of becoming an escort, but it sounds like his first night was certainly an enjoyable one!

I'm looking forward to your further efforts - you write so nicely!

 

[bulge]

Great work, man. And don't forget: being an escort makes a man out of a boy. Great work.

 

[ShihTzuTylenol]

I just hope those Grants aren't counterfeit, Seth seems a little naive. I don't want to see him taken advantage of...

 

[____]

I love reading this story . Great story.

 

[Toddxxx]

I definitely had conflicting thoughts that night. On one hand, I was repulsed by the thought that I was prostituting myself, offering my body for money. But on the other, I sure did not feel like a Rent-A-Boy whore while I was with Terry. He didn't make me feel dirty, not at all. I enjoyed sex with him, probably even better than with all the guys my age that I had fooled around with. Terry was the first older guy I slept with. No quick fuck with him. He made love to me, and so sensuously. It was a terrific experience.

The next morning I met Benjamin to get my money. "Hey, how did it go?” he asked.

"Okay I think,” I answered.

"Well, better than okay. It seems like you did real good, stud. He's coming back to town again in two weeks and wants to know if you can stay the night with him."

"For how much?"

"Double,” Benjamin replied.

"Three hundred? He can get a hell of a lot of me in one night you know,” I exclaimed.

"Three hundred, that's it. Take it or leave it, stud. You in?"

"I'm in! And stop calling me stud! You can be an asshole, you know."

“Got it! Now that that's settled I have another client wanting to meet you. He's a little kinky though".

"Kinky? Like how kinky?"

"Cross dresser, who likes to role play with young boys".

"Oh, shit! A weirdo!" I said, thinking that I was getting into stuff I didn't want.

"Cut the crap, Seth. Don't be so judgmental. He's a real big shot. He just has some fetishes that get him off. It's not unusual. Pretty common in fact,” Benjamin retorted, obviously annoyed.

"He probably wants me to fuck him then, right?” I asked.

"You can top, right?” Benjamin inquired.

"Yeah...., I can top when I have to. When does he want to play?"

"Sunday night. Same routine. I'll call you when I get his hotel and room number. And here's your money. Good job, Seth."


Benjamin called. Eight o'clock at the Marriott. The Marriott again? Wondered if that hotel knew all the stuff that was going on there or even cared. Guess it's not unusual. I knocked on door 216, more than a little anxious about my first encounter with a cross dresser and having no idea what he might want of me.

"I'm excited to meet you in person. Come in! You look even younger than in your photos. I like that,” he said. "Benjamin explained my special interests I hope,” he asked.

"Yes he did. Thank you,” I responded.

He removed his bath robe. He was wearing black stockings and very little panties with lace fringes that barely contained his stuff. "I like to dress up,” he admitted, which was pretty obvious.

What do you respond to that? "You look great,” was all I could think to say.

"I like smooth boys. I saw your pictures. Can you show me?"

I stripped. My cock was flaccid and I wondered if I could get it up for anything like this. He was sitting on the bed and beckoned me toward him. He cupped my balls and gently stroked my cock. Still limp. This will not work, I thought. He pulled me to him and began to suck me. Work my cock and I'll get hard regardless of the situation, and I did.

"I love young boys,” he spluttered. He was more of an eager than a good cocksucker. Regardless, getting your cock sucked vigorously always feels good. I got hard. I was far from coming when he asked if I wanted to fuck "Momma,” as he put it.

I was getting into his needs. "Momma wants to his boy to fuck him?” I asked, knowing what he wanted.

He turned over exposing his ass. He said nothing, just lowered his panties. I was still hard from his sucking. I stoked my cock a few times real hard. No problem entering him, real loose asshole. I pounded his ass for a few minutes, and then came in a burst of cum. Not my best orgasm, but okay. He was still hard so I jerked him off till he came. We collapsed onto the bed.

Where do I go from here?

 

[DonQuixote]

Todd,
I guess we're going to be treated to all manner of needs and desires - of a safe, high class clientele sort.

Mama wants her boys to bang her good, huh? lol

Looking forward to the next encounter.

 

[Toddxxx]

It would be quite an understatement to say that I was eager to spend an entire night with Terry. Before falling asleep each night I discovered myself dwelling on my brief encounter with him and getting aroused. Somehow my time with him seemed so much more than just the pleasure of good sex. He treated as a partner, an equal, not just a cheap trick he purchased to fulfill his secret sexual needs.

But wait! I'm getting ahead of myself. Benjamin set me up with yet another of his clients a few days before I was to be with Terry. This one was even worse than my experience with that cross-dresser. No hotel meet. He picked me up in the Wall-Mart parking lot. He was a geeky looking guy, maybe in his late thirties. I thought he might be a priest or something with the rosary beads hanging from the rear view mirror, but he had an infant seat strapped in the back, so I guess not.

We drove out of town and off onto a deserted dirt road. He turned the engine off and lowered his trousers and boxers to his knees, revealing his erect cock. There was not a single word exchanged before then until he said, “Go for it boy. I know you want it!" I wrapped my hand around his hard on and began stroking. "I'm not paying for a hand job. Suck me, slut!" he shouted. I leaned over and started to give him head, but with the steering wheel it was a bit awkward.

"Outside!” he ordered.

When I got around to his side of the car he was leaning against the hood, pants and underwear now at his ankles, cock up and ready. He pushed me down in front of him. He was real hairy and I hate going down on a bush. All my boyfriends, Terry too, were either smoothly shaved or at least well trimmed. Shit! Who likes a mouthful of hair anyway?

"Suck my dick, you little fagot,” he sputtered. He seemed to get off with dirty, demeaning talk. Bitch, queer, slut were slurs he repeatedly expressed while I sucked his cock and milked his hairy balls. He held my head and mouth-fucked me forcefully. Just before cumming he pulled me off and sprayed his juices over my face, then rubbed his cock all around my it in his cum.

"Like that, you little cocksucking fag?” he concluded. I never had a problem maintaining an erection and cumming while giving head to a boyfriend. But with this guy I never even got hard. I was glad when it was over. He drove me back to the Wall-Mart lot in silence. What a jerk, I thought!

That night I had trouble sleeping, wondering if this was really worth it. Sure, the money was good and I already had enough to make a major payment on what I owed the college. But so many desperate, closeted assholes out there who need to own up to themselves. What the hell should I do? Then I began to think about Terry and how beautifully he made love to me. I got aroused just remembering his tender touches and kisses. I slid of my briefs, edged for awhile before finally shooting off in my sheets and fell asleep on a real good note.

 

[DonQuixote]

Todd,
I guess not ALL of his clients are quite what you would call " high class".

Thanks for continuing to share with us.

 

[Toddxxx]

Finally, the day arrived when Benjamin called with Terry's hotel and room number - same hotel, different suite. I was excited, but also a little apprehensive. Maybe like with movies, I thought, the sequel is never as good as the original is remembered. I showered, taking shaving cream and safety razor in with me to remove any stubble from my pubes. "Smooth is a big plus,” Benjamin had advised. As usual, I got a hard on while shaving, but decided to leave it be this one time. After brushing my teeth and gargling I looked into my underwear drawer wondering what to wear. I held up a pair of pink, low rise briefs. Yeah, Terry will go for these. Another spontaneous erection arose as I pulled them on. Holy shit! I was so fucking hot, but again I let it subside unanswered. I was intent on saving all I had for him. So cool it, Seth, I cautioned myself.

Terry greeted me warmly. "You've been on my mind constantly." He pulled me to him and we kissed. "I just got in. You're a little early, but no problem." He was still in his business suit. I hesitated, not knowing if I should make the first move. He shed his jacket and tie and dropped his pants. I did too. He checked out my bulge in my hot pink briefs. "You are just fantastic,” he announced while smiling and cupping my crotch. He was wearing one of those CK white briefs with the red waistband and was obviously aroused. Our cocks met and engaged through our underwear as we hugged and kissed. No small talk this time. Terry sure wasn't wasting any time getting down to business and I was in no condition to complain.

Terry led me to the bed. I wanted to please him. I reached for his groin. I liked the idea of knowing I was the source of a man's arousal and I wanted this man badly. More caressing and kissing as we lay on the bed. He rolled me on my abdomen and began massaging my shoulders, back and especially my butt so nicely wrapped in pink.

"I am so ready for you, Seth,” he whispered. He pulled off my briefs, and his own also. His cock looked gorgeous as I watched him roll a lubed condom over it. He lay on his back, sheathed member pointing toward the ceiling. "Want a ride?” he invited.

I immediately straddled his body, facing him and lowered my ass to his waiting erection. Terry smiled as he positioned his cock on my hole. Two big deep breaths, my sphincter relaxed and he entered me. I liked the greater control of bottoming in this position. I could tell he was excited because right away he began strong pelvic thrusts while he held my hips. The sensation was intense. In literally minutes we were bouncing forcefully on the bed, both moaning in pleasure and working toward a quick, sexually satisfying climax. Terry came first. I could feel his pulsating cock unloading inside me. I grabbed my hard, moist cock and with a half dozen vigorous strokes exploded gobs of cum onto his chest and face. Fuck! That was awesome. I bent over on top of him in my own cum as we kissed.

"You know how to make an old man feel so damn good, you know,” he said.

"Hey, you're not that old. And you sure know how to fuck a boy,” I responded. We laid in silence for a while when Terry asked, "Have you been working for Benjamin long?"

"No. Only two weeks. You were my first client,” I replied. "I'd never do this if I didn't need the money so I can get through my senior year." immediately regretting saying that. There I was naked in bed with a man with whom I had just enjoyed a terrific orgasm and genuinely liked. "I'm sorry. I didn't mean that the way it may have sounded. I do like being with you, like it very much. I mean it!" Terry said that he understood and kissed me softly.

After a brief pause Terry said, "I envy you, and your generation."

"Me. Why?,” I asked.

"You seem so comfortable with who you are. Being gay, I mean. When I was your age there was no way. It wasn't possible to admit it. The consequences were too great. I settled for the only option available for me. I told myself that maybe I was bisexual, but increasingly I found myself needing to think about being with another man in order to maintain an erection while having sex with my wife. Born to early and missed out, I guess." I said nothing to his confession, but did understand and felt sad for him.

There was another longer pause. "Seth, do you ever top?"

I kissed him again, passionately. "Yes, I do!" I exclaimed.

 

[youngnihilist]

I'm guessing not a true story because some of the details are inconsistent with real life escorting, but still hot and well done.

 

[DonQuixote]

Todd,
Terry is a prince of a "trick". I can see that this is the only way he can enjoy his true sexuality, due to the generation in which he was raised.

I think he'd very much like to be intimate with our stud on a more regular basis.

Thanks for sharing with us.

 

[Toddxxx]

We lay together for maybe half an hour. Terry inquired about my studies, plans after college, ambitions and even my dreams. He seemed genuinely interested. I liked that. Liked the idea of him caring about me as a person, not just a boy to satisfy his hidden desires.

"Want to take a shower?" he asked. I nodded my consent. He rose and headed toward the bathroom. "You coming?" I joined him without hesitation.

With the refreshing warm water pouring over us we embraced and kissed. Terry started first with the bar of soap, washing my chest and back. I got aroused even before he got down to my groin and worried that I would cum prematurely when he began gently rubbing his soapy hands on my smooth cock and balls. I quickly took the soap from him and started washing him. His body was so attractive, trim yet soft. He leaned against the shower wall exposing his cute white ass to me in an incredibly inviting way. He moaned softly as I ran the bar of soap repeated over his crack. I wasn't sure, but from his reactions I thought I knew what he wanted. He sighed when I slipped a finger in his hole. I was so turned on.

"Let’s go back to bed, okay?" I suggested. We kissed again and dried each other off, both obviously primed for more sex.

He caressed my rigid cock briefly and then went down on me. He sucked me eagerly for a while before taking a condom from the nightstand and slipped it over my intense erection. He rolled over exposing his smooth white ass. I dove in and tongued his hole. He moaned loudly, shivering. I pulled him up onto his knees and gently pressed my sheathed erection on his tight, unyielding hole. I leaned over him and whispered, "Relax, Terry. Deep breaths."

His sphincter softened a bit. I pushed hard and he cried out as I entered him. I paused and waited for him to relax before starting to fuck him with long, slow strokes. His ass was so tight I had to wonder if this was his first time. It felt great. I leaned over, kissing him on his neck, as I picked up my stroke. He moaned repeatedly as I pounded his tight ass. I knew he was enjoying it, maybe even as much as I was. He was so tight it didn't take me long to reach an orgasm and I collapsed on top of him. One awesome fuck! When we disengaged Terry's cock was soft but there were wads of his cum on the sheets. I guess it did it for him too.

We lay quietly for a while. I wanted to ask if it was his first time getting fucked, but didn't have to.

"I've not done that before,” he admitted.

"Was it okay?” I asked.

"You know it was. Hell yes!" he replied and leaned over and kissed me.