Confessions of a Sugar Boy

Hi my name is Marko. I'm 28 years old, and I'm a Dentist. I am gay, and this story helped me decided to come out. This story is 100% true, and probably the best times of my life while I was at the end of Dental School. For privacy reasons some details have been changed. 

I was in my 3rd year of Dental School. The classes were getting easier, and I was able to start enjoying some free time from the hard classes and constant studying. I swam in college, and grew up swimming. Swimming was always important to me. I enjoyed wearing tiny speedos, and having a great swimmer's body. I was at the school's pool swimming like I always due. The pool is full of older overweight men who can't swim. There might be the occasional younger swimmer like me, but for the most part recreational. No one else at the pool wears a speedo. I love speedos, and always will. The best thing about being a swimmer is the excuse to shave your legs, so I still shave my legs. I am not a very hairy person, but my legs have always been really hairy. So, I shave my legs a couple times a week just to look cleaner when I swim. 

On a random afternoon I was swimming, and to my surprise I happened to get a glimpse of another guy wearing a speedo. This turned me on. He was a few lanes down from me, but was wearing a tight black speedo brand speedo...classic. He wasn't as good as me, but was decent. He looked really tall and tan. After a few more laps, I noticed the guy got in the lane next to me. I stopped at the wall to catch my breath. While I was on the wall, I heard the guy start talking to me.

He said "Hey man, don't see many other guys rockin' the speedo around here. I dig it." I said "No kidding." He introduced himself. His name was James. He was tall, and handsome. His hair was dark black and slicked back. His smile was perfect. We made small talk nothing serious. Then both got back to swimming. I could not stop thinking about how hot he was while I finished swimming that day. I jerked off a few times that night thinking about him. 

One week later, I was swimming my laps, and then I saw James standing above my lane. I stopped. I looked up, and all I saw was his huge bulge in his tight speedo. He asked if he could swim with me since all the other lanes were taken. I said sure. We swam separately for a little bit while he warmed up. We got to talking more, and I found out he was divorced. I told him I was in Dental school. He was impressed with how smart I was...I was impressed by how sexy he was. He didn't say, but I would guess he was 10 years older than me. He worked in finance downtown is all he said about his job. We swam, then talked, and swam more. We both got tired. I said I was going to go shower off and change. He followed me to the locker room. 

The showers were one big open area. I usually just rinse off while keeping my speedo on. I never use any shampoo or body wash, and just towel dry my hair when I'm done. Well, I was showering and then James walked into the shower naked with a dope kit full of bathroom things. I could not help but stare at his amazing body. His dick was huge. Not to mention he didn't have one hair on his entire body (which I guess I didn't notice before?). He wouldn't stop talking about stupid things, but I could not stop staring at him. I then decided to take off my speedo. I took it off, and hung it on the wall. I tried not to get rock hard, but it was impossible. I could smell his masculine body wash. I asked him if I could borrow it. He let me borrow all his things. I didn't really care about brands, but these looked like some expensive brands. Especially the Versace Body wash. It smelled amazing. I couldn't help but keep pouring that all over my body. He turned off his shower and walked to his locker butt naked and dripping wet. I finished using all his products. I could not figure out if he was gay or not? Some things he did made me think he was, but he acted very straight. Did he think I was gay? I tried my best to act straight around him. I turned off my shower, and grabbed my speedo. 

His locker was 2 away from mine...He said "what are the odds?" His hair was dripping wet and slicked back. He had amazing hair. He said he came from work, and had to put his suit back on. I just had jeans and a Tshirt. He was talking, and asked what I was doing for dinner since it was about 5:00. I said nothing, and he asked me if I wanted to go to dinner with him just as a couple guys getting a beer and food..."nothing weird" he added. I said "sure why not?" He asked me if I had been to a certain restaurant, I had not...and if I was thinking about the right place it was really expensive? He said it was a little more formal. I said I only had jeans and a Tshirt. He then said I could borrow some of his clothes if I didn't mind going to his place real quick. I said no that fine, and he had already offered to drive. We finished changing, and walked out his car. His long black hair was still wet and slicked back. His suit looked very expensive and perfectly tailored. My hair was a mess, and my outfit was sloppy compared to his. He unlocked his car, and the headlights to a brand new Range Rover went off. I couldn't believe he would drive that nice of a car? I said nice car, and he said he just got it. I got in his car, and we started driving downtown. 

We were in the car making small talk, and we got downtown to the nicest building. He pulled up to the front of the building, and we got out. I couldn't believe he lived in the most expensive building in the city. He handed the valet worker a $20 bill to park his car. As we walked through the lobby, I could not help but notice how fancy it was. There were shops, and rich people everywhere. Then, the front desk yelled his name. We walked over there, and they asked James "are you here for your hair appointment?" James had forgot he had a hair appointment that was scheduled for 5 min ago. He asked if I cared if he went and got his haircut, I didn't care. He said I could just watch and wait. The building was so nice and fancy. We got to the salon in the basement, it was the nicest salon I had ever been too. We walked to the back of the shop where a small Italian guy was is in the back waiting on James. 

James hands me his suit jacket and tie, while he unbuttons his white dress shirt. The barber and James are making small talk. After about 20 minutes they were done with his hair. James looked amazing. His hair was still long on top, but the sides had been taken in. It was slicked back with pomade. Then, the barber put his chair down and started shaving his face...I had never seen a guy get his faced shaved at the barber...it was quite sexy. I was getting a little hard. 10 minutes later he was done. James' face was clean shaven to go with his slicked back hair. He looked even more sexy. 

Then, James pointed at me and said "You're next." James had sweet talked the barber into cutting my hair. I hadn't had my hair cut in 6 months. It was long. My hair was dark brown and bushy. I didn't do much with it ever, sometimes I put some gel in it if I needed to look more professional. I sat down and he put the cape around me while James and the barber stood behind me talking about hair options. They agreed on something, and the barber got to work. He grabbed his clippers and took a lot of hair off the sides...leaving plenty on top. He then got out his scissors and cut a few stray hairs. He washed my hair, and then blow dried it backwards. After several minutes of blow drying my hair, he grabbed some gel and slicked my hair backwards, then parted it on the side. I looked in the mirror. I had never looked so sophisticated or smart. I looked like a real gentleman. Then, the barber did it...he lowered my chair, and started putting shaving cream on my face...then a hot towel. He removed the towel, and then put more shaving cream on my face. Then, the razor was pressed against my face. It felt funny, but very sexy. 10 minutes later, he put my chair up and I saw a completely clean shaven smooth face. I looked so handsome. Then, he asked if I had ever had my eyebrows waxed. I said no...my eyebrows were a little bushy, but I didn't think they looked bad? He then put some hot wax on my eyebrows, and pulled...it hurt. But, they looked fabulous. I looked like a different person. The barber then washed my entire face off with some sweet smelling lotion. Followed by a lot of after shave. It burned, but smelt very masculine. 

We left the salon both looking good. We got to the elevator, and James pushed one of the buttons on the top row. James looked over at me, and said "You look like a new man!" I thanked him for the compliment. He then said "That he couldn't go to dinner with someone that didn't look their best." I agreed with him...I could have used the help of a small makeover. There was tension in the elevator. Then, James did something I was not expecting. James touched my clean shaven face, and said "Don't you love the way that feels?" I could not help but think James left his hand on my face for a very long time. I said "My face feels very smooth." He then asked if I wanted to touch his face...I felt obligated to touch it...so I ran my hand along his chiseled jaw line. It was very smooth. I could feel my penis throbbing. The elevator kept going up and up. Then finally we reached the top floor. James owned the penthouse. The doors opened and his apartment was incredible. 

We walked in...then James started taking off his clothes. He said we had dinner reservations in 20 minutes so we needed to hustle. I followed him to his closet. The closet was full of suits and dress clothes. With one whole wall full of shiny dress shoes. James had already taken off all his clothes except for his underwear. They were tiny white Calvin Klein briefs. His dick was packed perfectly in the front. He told me to hurry up and take off my clothes, so he could figure out what to give me. I stood there in just my Nike compression shorts. He laughed, and said "that underwear will not work with suits." He tossed me some underwear. I caught it in my hands. It felt small. As I looked at it...it was an Emporio Amrmani black thong with a gold waistband. I took off my compression shorts, and slid the smooth cotton fabric over my body. They were small, but just the right size. I had never worn a thong before. It felt incredibly sexy. It was tight on my dick, and my ass pinched the back just right. James said "Those fit you perfectly!" I nodded yes. We were both standing there in just our sexy underwear. It was very hot. Then, James picked out a suit for me. It was dark charcoal. He handed it to me, and then handed me a plain white dress shirt. I quickly put on the shirt and then the suit pants. They both fit perfectly. I thought everything would be too big, but it fit just right. James put on a black pin striped suit with a white dress shirt. James then handed me a pair of shiny black dress shoes. I asked for a pair of socks, but he said I didn't need them. He said "Guys your age look good without dress socks. Its the new trend." So I put on the shoes. James put on a pair of black leather dress boots. They were so sleek and sexy. We were still feeling rushed to hurry and get to the restaurant. James came up from behind me, and said "I think you should wear a tie." So, he grabbed one, and then put it around my neck. His face was so close to mine. I could smell the after shave on his face. James tied my tie tight, and then said "I think thats good." He didn't wear a tie...his dress shirt was left unbuttoned, and you could see some of his chest. James said "One more thing before we go." He walked to his bathroom, and said "Which one do you want?" There were at least 10 bottles of cologne on a counter. I had no idea which one would be good...I never wore cologne. Then, James said "I will pick for you." He grabbed a Versace bottle, and then sprayed at least 8 sprays of cologne all over me...James said "I think you have to smell good all the time. Don't you?" James picked up a different bottle, and then gave him self a generous amount of cologne. I could start to smell myself, I smelled very strong and masculine...It made my dick hard. I caught a glimpse of myself in the mirror, just as we were about to get in the elevator. I was hot. I looked like a movie star. My hair was perfect, clean shaven face, and tight fitting suit. James looked really good too...As we rode down the elevator I got a bit of an erection. I didn't want to make things weird. We were just two good looking guys going for dinner as friends. 

We walked out of the lobby, and a black Bentley was waiting in front of the building. James walked towards it...He then said "Get in man, we are late!" So, I got in another one of his cars. It was very nice and very expensive...I was beginning to think James was very very rich. We talked about the car for a while. Then James said "Mark you look very handsome. I am very proud of myself. I managed to make you look handsome enough to be my date tonight." I thought date was a weird choice of words...but I said "Thanks! You look really good too James." He smiled back at me and winked...I was unsure why he winked at me...I think I had a different idea of what was happening.

We pulled up to the very fancy restaurant. James got out, and then quickly went to my door. James opened my door for me. I was confused, but thought I would just go with it. James reached for my hand. I grabbed it thinking maybe it was a hard car to get out of? James grabbed by hand, and the would not let go of my hand. He then put his arm around my shoulder, and kissed my cheek. He then whispered in my ear "You are mine for the night." I didn't move...I had thought about pushing him off me, but I thought that would be a bad idea. So, I just walked next to him. We got to the door, and he said "after you honey." The hostess said "Hi James welcome back. This must be your boyfriend." I didn't know what to do...I just smiled and nodded to the young girl. We followed her to the table, and James' arm was around my shoulder the whole time walking...I had never been gay out in public like this...I was nervous, and several people were starring at us? I secretly liked it...a lot...I was still confused though? Was James gay? 

We sat and ate dinner. James kept grabbing my knees under the table, and then my wrists above the table. Constantly touching me...as his way of keeping me from running...little did he know...I was not interested in running...This was sort of a fantasy of mine...James just didn't realize that. We had a couple glasses of champagne with our dinner. We were talking about random things. School and work. Then, dinner was over, and it was time to leave. 

James stood up first, and then grabbed my hand. We held hands until we made our way to the front to get back in his Bentley. James opened my car door for me, and let me in. Then, James got in the drivers seat. We were both quiet. Then, James asked me "Are you okay with how things are going?" I didn't know what to say, and then I said "sure." He said "You know Mark, I saw the way you were watching me swim, and you would not stop starring at my dick in the showers." I nodded. James then said "I am in the market for a good sugar boy to be my companion." I didn't say anything. James then said "You know, I'm sure you could use the money. Tonight was a test to see if you could look hot enough to be my sugar boy...and you passed. You looked so hot this evening." I blushed a little. I then said "Thank you for giving me a makeover, and I enjoy spending time with you. I just don't know what a sugar boy means?" James then said "I will pay you to hang out with me. You are a very handsome man, and if it leads to the bedroom then no big deal, right?" I was nervous...but secretly very excited and horny. I said "Ok." 

We made it back to the building, and back inside to the Penthouse. James poured us both some drinks. James left for a few minutes then came back. He was wearing just a short black silk robe. He told me to go change out of my suit and put on the other robe. I got up and walked to the closet. There was another dark grey robe sitting in the middle of the closet. I took off my clothes and put on the robe. It was the sexiest robe ever. It ended in the middle of my thighs. I thought I should be careful, or my dick could hang out. I walked past the bathroom. I walked inside and looked at myself in the mirror. Who was this new Mark? I looked very handsome and sexy. Did I look gay? I didn't think so, but it definitely was not as "straight looking" as before. I took a couple deep breaths. I didn't really know what was going to happen, but I think deep down inside I was very happy. As I was about to leave, I saw all the cologne bottles. I thought what the heck? Why not make myself smell good. I picked up the bottle on the end. I opened up my robe, and sprayed some on my chest and all the way down to my dick. It burned for a quick second, then I could start to smell it. It smelled amazing. 

I walked back to the living room. James was laying on the black leather couch. He then said "Come sit next to daddy." My dick started to pulse. I sat next to him, not too close though. He then scooted closer to me. He then put his arm around me, and said "did you use some cologne?" I blushed a little. I said "I did...I could not help it..." He was impressed with me. He then kissed me on the cheek. He asked me if I liked that. I replied with "yes." He then put his hand in my robe, massaging my chest and stomach. My dick started to grow. He leaned over then kissed me on the lips. This was the first time a man had kissed me on the lips...I lost it...My dick was exploding, and I was horny as hell. We were making out, tongues going back and forth. James stopped, and asked me "If I wanted to go to the bedroom." I paused for a second and then said "yes." James stood up and took off his robe. His dick was hard. He reached for my hand, and I stood up...He untied my robe for me. My dick was hard too. He held my hand as we walked to his bedroom. 

We stood at the foot of the bed, and James pushed me down by my shoulders. He said "alright boy, get to work." I put his huge dick in my mouth. It felt weird. I had never given a blow job before. I started liking it more and more. I felt myself trying to get every inch of the dick in the back of my throat. He grabbed the back of my head and shoved my head into his dick. I gagged a little, but kept going. He then, pulled me up, and kissed me. Then he said "My turn." He got down, and put his mouth around my dick. It instantly felt amazing. After a couple minutes I thought I was going to cum. I said "I think I might cum." He stopped, and then said "Not without you getting your hole stretched out. You have to earn that cum." He tossed me on the bed, and then shoved his dick up my ass. I was not ready, but he just plowed into me. I was screaming in pain, but it started to hurt less and less. After a few minutes It actually started to feel really good. I started begging him to go harder and harder. It was amazing. I had never felt such pleasure and pain before. After 10 minutes of him pounding my ass, he pulled his dick out of my newly loosened hole. He stroked his dick back and forth. Then turned me over on my back. He said "Get ready for it." His dick was right next to my face. He said "open wide." I didn't know what to do, so I just opened my mouth. Seconds later he shot his load into my mouth. It was so hot. It tasted funny. I thought I might gag, so i spit a little out. He then licked that off my face. I swallowed a little bit. He said "your turn." He started sucking my dick again. I was rock hard, and about to blow. I said "I'm going to cum!" He said "do it!" I shot my load in his mouth. He swallowed every bit of it...or so I thought. He finished sucking me dry. Then kissed me on the lips, spitting some of my cum in to my mouth. I had no choice, but to swallow it. I didn't really care anymore, I was on such a high from having sex for the first time with a man.

We sat there on the bed for a few minutes while we caught our breaths. We cleaned ourselves off. Then put our robes back on. 

After that night I stayed over at his pent house for the rest of my time in Dental school. He payed for some of my school, and spoiled me with many fancy things. We had so many wonderful adventures. I still text James sometimes. He moved on with another sugar boy, but always invites me to go back. I think about it sometimes, but I'm too busy with work right now. Maybe sometime in the future? It was a great relationship full of love, money, and mostly sex. I was a sugar boy. I eventually came out to my friends and family with the help of James. I don't think I will ever find a man as good as James.