My Straight Best Friend in Medical School - True Story

Next encounter with Rob.

This time, for context, I do want to mention again that Rob was handsome and a big flirt.

The day after our last encounter, I noticed that Rob seemed grumpy and distant. I knew right away that he probably was angry about what occurred the previous night. I stayed away and acted diplomatic to keep the peace so we could go on with our daily routine. I knew that at some point we were going to talk things out and resolve this. 2 days passed. That day we had long planned to complete a pathology assignment together. I wasn’t sure if we would even do it but it was important to finish. He told me that we need to talk things out, clear some air first so that we can get to working on our assignment. I said fine. We waited till the other housemates left for dinner and we had some alone time. He told me that he was mighty pissed with himself that he went as far as a blowjob with another guy. I told him that it happened only after he consented to it. He asked why I would give a guy a blowjob just because they asked. I told him that I don’t have any qualms about it since it was him and how close we were. That we were so emotionally connected. He again blamed me partly for not stopping it from happening. We argued and went back and forth. We concluded that we weren’t going to let it happen again. But I also warned him that I would not proactively stop myself if he asked for it. He said he would never ask for it again. Or so he thought.

A bunch of us friends traveled to another city for a mini vacation. Rob and my girlfriend went with us. His girlfriend couldn’t make it. We all crashed at a mutual friend’s place to save money. This mutual friend’s cousin (girl) hung out with us on a night out. Rob was heavily flirting with her all night. We wanted weed and the girl had a connection. She asked Rob to go with her to pick it up. They came back after a couple of hours. I looked at Rob and he winked. That was his way of telling me that he banged her and he was happy. I gave him a thumbs up. The next day, Rob told everyone that he had to go meet an old friend. But he told me his secret that he was going to hang out with that girl. He didn’t want his girlfriend finding out so had to do this on the sly. He came back the next morning. He seemed tired but cheerful. He told me that he had some juicy details to share.

We came back home from our vacation. 2 days went by but we never got a chance to hang out and talk. It was a weekday evening, we didn’t have any plans, not much was going on with school work so we decided to smoke some weed and drink the scotch we bought during our vacation.. We decided not to invite anyone else as he was eager to tell me about his rendezvous with that girl. We had the house to ourselves. We started drinking the scotch and toked. He finally told me details about the wild night that he had. He had his first threesome with 2 girls and it was a long time fantasy that came to fruition! He came back a happy man. The girl brought a friend of hers and they all met at a bar, drank and decided to check into a hotel for some fun. He described in gory detail about all the things that they did. They first did it on the bed, various positions. He described how he always fantasized about eating a girl’s pussy for hours all the while getting a blowjob by another girl. He got to fulfill his fantasy. He actually came during that act and the girl happily swallowed his cum. Then they sat around for a couple of hours, smoking, drinking, talked about their sexual fantasies. One of the girls did ask him if he ever had sex with another guy and he told them no and that it does not turn him on one bit. They decided to go at it again but this time in the large shower stall in the bathroom just to spice things up. They soaped each other, he got to finger them both at the same time, took turns in fucking them both, tried fucking one of the girls anally for the first time and more. He described the experience as being in sex-heaven.

He lamented how his girlfriend is not sexually adventurous and that he would continue hooking up with other girls to fulfill his fantasies. He asked me how I handle my fantasies, if I would pursue them, about my girlfriend, if I am open to hooking up with other girls. He wanted me to describe my girlfriend’s pussy and what it tasted/felt like. At times I wondered how erotic and sexually charged the whole atmosphere was getting with all the sex talk. I could see that he was walking around with a boner in his shorts. I was rock hard in my shorts as well. He would sub-consciously give his cock a tug or adjust his cock while we were talking. But I told myself that if anything was to happen, he would have to make the first move and give me clear consent. Otherwise, I told myself that I’ll just jerk-off before hitting the bed. I had to. I was totally turned on.

The conversation turned to blowjobs and we were comparing notes. He said something that still stays with me even today. He said there are things that I did during the blowjob that I gave him that felt different in a nice way. That it took the blowjob to another level compared to all the blowjobs that he got from the girls. I responded that it may be because that only a guy would know exactly the right spots, sensations, pace/pressure which would in turn affect the cock-brain axis. In hindsight, I think that the weed/alcohol combination played a big role in such an uninhibited conversation. He did ask if I was enjoying my blowjobs from my girlfriend. I told him that they were fine and do feel good. He then asked if I ever tasted my own cum. I said no but that I tasted my pre-cum. He asked if it tasted any different from his pre-cum and I said I didn’t feel any difference. I asked him if her ever did. He said he tried to one time but the first lick of cum from his hand felt disgusting so he spit it out. He asked if I had any inhibitions in tasting cum. I told him that I probably wouldn’t taste my own because once I orgasm I would probably lose any drive to do it. He reflexively asked if I would ever taste another guy’s cum. And I reflexively responded yes, if it is your cum but probably not with anyone else (I lied). He gave a surprised look and said wow. I teased him not to get any dirty ideas. He said no way. Then we said let’s call it a night as it was way past midnight and the housemates might be back anytime. He said he wanted to jerk-off and asked me to stay out in the living room until then. I told him that he could do it in the bathroom as I was sleepy. He wasn’t thrilled with the idea but said okay. I was pretty turned on too so I told him that I’ll let him go first and then I will jerk-off after him. I was in my bed when he walked into the room 2 minutes later. I was surprised and asked are you done already? You take so much time to cum usually? He said he just peed and didn’t jerk-off. He said he thought about it and was wondering if a blowjob would be better. I said, are you asking me? He said yes. I reminded him that he would get angry the next day. He said he wanted to experience those sensations again and assured me that he would not get pissed. I smiled. He took that as a yes and locked the door from the inside.

He asked if he could fuck my mouth. I told him that sounded too hardcore and unsure if I’d able to pull it off considering his size. He didn’t ask the lights to be turned off so that was surprising. He took off his shirt, shorts and undies and lay on the bed. This was actually the first time I was seeing his naked body with all the lights on. I stroked his cock a bit and smelt it. That felt so damn good. I started sucking his cock. This time I was using a lot of saliva and slobbered all over his cock. I could see that he was loving it. I asked if I could lick his balls. He said go for it and I did. He was moaning and dripping pre-cum. I tasted that and loved it. I was really enjoying pleasuring him so in that spirit I told him to stand so he could try and fuck my mouth but to be gentle. He stood up and I told myself that he really had a nice ass. I grabbed his buttocks and he slowly started thrusting his cock into my mouth. Then he kept increasing his pace. After a point I had to stop him as it was too big to take. I told him to sit on the chair. I started slobbering over his cock again. He was pushing his hips up and thrusting it in too. He said he was going to cum. I didn’t respond and continued sucking him and he blew a huge load into my mouth. He said that felt like a volcanic explosion and he really loved it.
Any pics? Either of you?
 
Next encounter with Rob.

This time, for context, I do want to mention again that Rob was handsome and a big flirt.

The day after our last encounter, I noticed that Rob seemed grumpy and distant. I knew right away that he probably was angry about what occurred the previous night. I stayed away and acted diplomatic to keep the peace so we could go on with our daily routine. I knew that at some point we were going to talk things out and resolve this. 2 days passed. That day we had long planned to complete a pathology assignment together. I wasn’t sure if we would even do it but it was important to finish. He told me that we need to talk things out, clear some air first so that we can get to working on our assignment. I said fine. We waited till the other housemates left for dinner and we had some alone time. He told me that he was mighty pissed with himself that he went as far as a blowjob with another guy. I told him that it happened only after he consented to it. He asked why I would give a guy a blowjob just because they asked. I told him that I don’t have any qualms about it since it was him and how close we were. That we were so emotionally connected. He again blamed me partly for not stopping it from happening. We argued and went back and forth. We concluded that we weren’t going to let it happen again. But I also warned him that I would not proactively stop myself if he asked for it. He said he would never ask for it again. Or so he thought.

A bunch of us friends traveled to another city for a mini vacation. Rob and my girlfriend went with us. His girlfriend couldn’t make it. We all crashed at a mutual friend’s place to save money. This mutual friend’s cousin (girl) hung out with us on a night out. Rob was heavily flirting with her all night. We wanted weed and the girl had a connection. She asked Rob to go with her to pick it up. They came back after a couple of hours. I looked at Rob and he winked. That was his way of telling me that he banged her and he was happy. I gave him a thumbs up. The next day, Rob told everyone that he had to go meet an old friend. But he told me his secret that he was going to hang out with that girl. He didn’t want his girlfriend finding out so had to do this on the sly. He came back the next morning. He seemed tired but cheerful. He told me that he had some juicy details to share.

We came back home from our vacation. 2 days went by but we never got a chance to hang out and talk. It was a weekday evening, we didn’t have any plans, not much was going on with school work so we decided to smoke some weed and drink the scotch we bought during our vacation.. We decided not to invite anyone else as he was eager to tell me about his rendezvous with that girl. We had the house to ourselves. We started drinking the scotch and toked. He finally told me details about the wild night that he had. He had his first threesome with 2 girls and it was a long time fantasy that came to fruition! He came back a happy man. The girl brought a friend of hers and they all met at a bar, drank and decided to check into a hotel for some fun. He described in gory detail about all the things that they did. They first did it on the bed, various positions. He described how he always fantasized about eating a girl’s pussy for hours all the while getting a blowjob by another girl. He got to fulfill his fantasy. He actually came during that act and the girl happily swallowed his cum. Then they sat around for a couple of hours, smoking, drinking, talked about their sexual fantasies. One of the girls did ask him if he ever had sex with another guy and he told them no and that it does not turn him on one bit. They decided to go at it again but this time in the large shower stall in the bathroom just to spice things up. They soaped each other, he got to finger them both at the same time, took turns in fucking them both, tried fucking one of the girls anally for the first time and more. He described the experience as being in sex-heaven.

He lamented how his girlfriend is not sexually adventurous and that he would continue hooking up with other girls to fulfill his fantasies. He asked me how I handle my fantasies, if I would pursue them, about my girlfriend, if I am open to hooking up with other girls. He wanted me to describe my girlfriend’s pussy and what it tasted/felt like. At times I wondered how erotic and sexually charged the whole atmosphere was getting with all the sex talk. I could see that he was walking around with a boner in his shorts. I was rock hard in my shorts as well. He would sub-consciously give his cock a tug or adjust his cock while we were talking. But I told myself that if anything was to happen, he would have to make the first move and give me clear consent. Otherwise, I told myself that I’ll just jerk-off before hitting the bed. I had to. I was totally turned on.

The conversation turned to blowjobs and we were comparing notes. He said something that still stays with me even today. He said there are things that I did during the blowjob that I gave him that felt different in a nice way. That it took the blowjob to another level compared to all the blowjobs that he got from the girls. I responded that it may be because that only a guy would know exactly the right spots, sensations, pace/pressure which would in turn affect the cock-brain axis. In hindsight, I think that the weed/alcohol combination played a big role in such an uninhibited conversation. He did ask if I was enjoying my blowjobs from my girlfriend. I told him that they were fine and do feel good. He then asked if I ever tasted my own cum. I said no but that I tasted my pre-cum. He asked if it tasted any different from his pre-cum and I said I didn’t feel any difference. I asked him if her ever did. He said he tried to one time but the first lick of cum from his hand felt disgusting so he spit it out. He asked if I had any inhibitions in tasting cum. I told him that I probably wouldn’t taste my own because once I orgasm I would probably lose any drive to do it. He reflexively asked if I would ever taste another guy’s cum. And I reflexively responded yes, if it is your cum but probably not with anyone else (I lied). He gave a surprised look and said wow. I teased him not to get any dirty ideas. He said no way. Then we said let’s call it a night as it was way past midnight and the housemates might be back anytime. He said he wanted to jerk-off and asked me to stay out in the living room until then. I told him that he could do it in the bathroom as I was sleepy. He wasn’t thrilled with the idea but said okay. I was pretty turned on too so I told him that I’ll let him go first and then I will jerk-off after him. I was in my bed when he walked into the room 2 minutes later. I was surprised and asked are you done already? You take so much time to cum usually? He said he just peed and didn’t jerk-off. He said he thought about it and was wondering if a blowjob would be better. I said, are you asking me? He said yes. I reminded him that he would get angry the next day. He said he wanted to experience those sensations again and assured me that he would not get pissed. I smiled. He took that as a yes and locked the door from the inside.

He asked if he could fuck my mouth. I told him that sounded too hardcore and unsure if I’d able to pull it off considering his size. He didn’t ask the lights to be turned off so that was surprising. He took off his shirt, shorts and undies and lay on the bed. This was actually the first time I was seeing his naked body with all the lights on. I stroked his cock a bit and smelt it. That felt so damn good. I started sucking his cock. This time I was using a lot of saliva and slobbered all over his cock. I could see that he was loving it. I asked if I could lick his balls. He said go for it and I did. He was moaning and dripping pre-cum. I tasted that and loved it. I was really enjoying pleasuring him so in that spirit I told him to stand so he could try and fuck my mouth but to be gentle. He stood up and I told myself that he really had a nice ass. I grabbed his buttocks and he slowly started thrusting his cock into my mouth. Then he kept increasing his pace. After a point I had to stop him as it was too big to take. I told him to sit on the chair. I started slobbering over his cock again. He was pushing his hips up and thrusting it in too. He said he was going to cum. I didn’t respond and continued sucking him and he blew a huge load into my mouth. He said that felt like a volcanic explosion and he really loved it.
Dang that a lot
 
My next encounter with Rob.

I could sense that Rob was getting comfortable with the idea of being naked around me . The fact that he didn’t get mad after our last super-charged sexual encounter was comforting for me. I was fighting my own battle in my head. I would crave for the moments to openly talk about sex and also for our sexual encounters to never end. But the friendship was more important for me so I had to work extra hard not to seem desperate to get in bed with him. I had to put up an external attitude that if it happens then fine. If it doesn’t then that is fine as well.

One day, out of the blue, he asked me if I could help him with shaving his pubic area again as he felt that I did a great job. Of course I said yes. A couple of days later, it was around the evening time. He was going in for a shower and asked if am free to help him with the shaving. Yes was my answer. He got his gear ready. I told him to wash off with soap once and then shaving would be cleaner. He did. I went in and immediately noticed that he had a hardon. I didn’t comment on it and nonchalantly applied the shaving cream and stared shaving. I could see that his cock was bobbing at times. I of course had to hold it a a few times to get a close shave. I shaved his balls and was shaving his inner thigh area when I noticed and asked if he wanted me to shave his taint. He said sure. I tried but it was kinda tough doing it while he was standing. I told him that he needs to sit on some thing and spread his legs. We went back into the room as we had a bench in there. Locked the door. He laid on the bench, got into position and spread his legs apart. This was a good angle and I was shaving his taint and super turned on to be staring at his asshole. I so wanted to touch it so I casually mentioned that there is hair around his anus. He said shave it off. Damn! My heart jumped with joy. I took my time to apply the shaving cream,, slowly shaving each spot, took every chance to touch his hole. He didn’t flinch at all and seemed very comfortable. I was done. On purpose, I asked him to touch himself and feel the clean shaven taint and asshole. He did and that was so hot watching him touch and feel his hole. I was hoping he would ask for a blowjob but he didn’t. That was disappointing. He jumped into shower and am pretty sure he jerked off.

Some days later, he made plans to hook-up with the girl he had a threesome with. He was really excited to spend 2 days with her. He told me that he probably would come back with wild stories for me. He spent the 2 days with her and got back home. I was eagerly waiting for him to describe his wild getaway. He kept teasing me that he had some wild times with this girl. We had to wait for a couple of more days for some alone time. So it was just the 2 of us at home that night and that was our chance to have our secret conversations. We got the booze and he started telling me all about his wild adventures. This girl knew he was up for some wild times and he tacitly consented to it. The first day he fucked her twice. He described all the positions and the types of foreplay. That evening they were going out for a drink. She said a friend of hers would meet them at the bar. They were at the bar and this guy walks towards them. And that was her friend. Rob was puzzled for a moment and quickly realized that she was setting up a threesome with another guy. He got a little nervous but didn’t wanna ruin things with her so he went along with it. They drank, talked and socialized at the bar. She told Rob that this friend (Jake) was her friend with benefits and that she had many threesomes with him. Rob asked if it was with 2 girls or 2 guys. Jake responded both. The girl took it for granted that Rob would not say no. Both of them checked with Rob if he was cool with it. Rob told them it would be his first time but he doesn’t mind trying it. Jake told him that he was straight and Rob said the same. They all went back to the hotel. Once in there, the girl took total control and guided them with each act. They both took turns in fucking her in different positions. Rob ate her pussy out while she gave him a blowjob and they changed positions. She wanted the guys to cum on her belly. Jake ejaculated first and sprayed it all over her belly. Then Rob sprayed his cum on top of his. After that, they sat around, talked, got back into it again. But this time it was just foreplay. Rob mentioned that at one point she was licking Jake’s asshole and that surprised him. I had so many questions in my head but had to use a filter and asked straight-ish questions only. Jake wanted to stay over the next day as well but he had to get back to work. After he left, Rob and the girl spent time together. He fucked her one more time before he came back home. The kicker was she promised him a foursome with another couple for the next visit.

This whole conversation was such a turn-on for the both of us. At times, Rob was grabbing his cock through his shorts and it was rock hard. He kept saying that talking about the sex was making him super horny. I asked if he wanted a blowjob and he said yes please! Locked the door, took his shorts off, he took his shirt off. He was dripping with pre-cum. I licked it off. Sucked his cock, licked his balls, he fucked my mouth. This time I wasn’t afraid to lick his taint and he didn’t flinch. In fact he seemed like he was enjoying it. I made it seem like I was just licking his balls and the area around it. He seemed very comfortable grabbing my head while I had his cock in my mouth. He finally came inside my mouth and I happily swallowed his load.
 
My next encounter with Rob.

I could sense that Rob was getting comfortable with the idea of being naked around me . The fact that he didn’t get mad after our last super-charged sexual encounter was comforting for me. I was fighting my own battle in my head. I would crave for the moments to openly talk about sex and also for our sexual encounters to never end. But the friendship was more important for me so I had to work extra hard not to seem desperate to get in bed with him. I had to put up an external attitude that if it happens then fine. If it doesn’t then that is fine as well.

One day, out of the blue, he asked me if I could help him with shaving his pubic area again as he felt that I did a great job. Of course I said yes. A couple of days later, it was around the evening time. He was going in for a shower and asked if am free to help him with the shaving. Yes was my answer. He got his gear ready. I told him to wash off with soap once and then shaving would be cleaner. He did. I went in and immediately noticed that he had a hardon. I didn’t comment on it and nonchalantly applied the shaving cream and stared shaving. I could see that his cock was bobbing at times. I of course had to hold it a a few times to get a close shave. I shaved his balls and was shaving his inner thigh area when I noticed and asked if he wanted me to shave his taint. He said sure. I tried but it was kinda tough doing it while he was standing. I told him that he needs to sit on some thing and spread his legs. We went back into the room as we had a bench in there. Locked the door. He laid on the bench, got into position and spread his legs apart. This was a good angle and I was shaving his taint and super turned on to be staring at his asshole. I so wanted to touch it so I casually mentioned that there is hair around his anus. He said shave it off. Damn! My heart jumped with joy. I took my time to apply the shaving cream,, slowly shaving each spot, took every chance to touch his hole. He didn’t flinch at all and seemed very comfortable. I was done. On purpose, I asked him to touch himself and feel the clean shaven taint and asshole. He did and that was so hot watching him touch and feel his hole. I was hoping he would ask for a blowjob but he didn’t. That was disappointing. He jumped into shower and am pretty sure he jerked off.

Some days later, he made plans to hook-up with the girl he had a threesome with. He was really excited to spend 2 days with her. He told me that he probably would come back with wild stories for me. He spent the 2 days with her and got back home. I was eagerly waiting for him to describe his wild getaway. He kept teasing me that he had some wild times with this girl. We had to wait for a couple of more days for some alone time. So it was just the 2 of us at home that night and that was our chance to have our secret conversations. We got the booze and he started telling me all about his wild adventures. This girl knew he was up for some wild times and he tacitly consented to it. The first day he fucked her twice. He described all the positions and the types of foreplay. That evening they were going out for a drink. She said a friend of hers would meet them at the bar. They were at the bar and this guy walks towards them. And that was her friend. Rob was puzzled for a moment and quickly realized that she was setting up a threesome with another guy. He got a little nervous but didn’t wanna ruin things with her so he went along with it. They drank, talked and socialized at the bar. She told Rob that this friend (Jake) was her friend with benefits and that she had many threesomes with him. Rob asked if it was with 2 girls or 2 guys. Jake responded both. The girl took it for granted that Rob would not say no. Both of them checked with Rob if he was cool with it. Rob told them it would be his first time but he doesn’t mind trying it. Jake told him that he was straight and Rob said the same. They all went back to the hotel. Once in there, the girl took total control and guided them with each act. They both took turns in fucking her in different positions. Rob ate her pussy out while she gave him a blowjob and they changed positions. She wanted the guys to cum on her belly. Jake ejaculated first and sprayed it all over her belly. Then Rob sprayed his cum on top of his. After that, they sat around, talked, got back into it again. But this time it was just foreplay. Rob mentioned that at one point she was licking Jake’s asshole and that surprised him. I had so many questions in my head but had to use a filter and asked straight-ish questions only. Jake wanted to stay over the next day as well but he had to get back to work. After he left, Rob and the girl spent time together. He fucked her one more time before he came back home. The kicker was she promised him a foursome with another couple for the next visit.

This whole conversation was such a turn-on for the both of us. At times, Rob was grabbing his cock through his shorts and it was rock hard. He kept saying that talking about the sex was making him super horny. I asked if he wanted a blowjob and he said yes please! Locked the door, took his shorts off, he took his shirt off. He was dripping with pre-cum. I licked it off. Sucked his cock, licked his balls, he fucked my mouth. This time I wasn’t afraid to lick his taint and he didn’t flinch. In fact he seemed like he was enjoying it. I made it seem like I was just licking his balls and the area around it. He seemed very comfortable grabbing my head while I had his cock in my mouth. He finally came inside my mouth and I happily swallowed his load.
Wow I can't wait for the next one
 
My next encounter with Rob.

I could sense that Rob was getting comfortable with the idea of being naked around me . The fact that he didn’t get mad after our last super-charged sexual encounter was comforting for me. I was fighting my own battle in my head. I would crave for the moments to openly talk about sex and also for our sexual encounters to never end. But the friendship was more important for me so I had to work extra hard not to seem desperate to get in bed with him. I had to put up an external attitude that if it happens then fine. If it doesn’t then that is fine as well.

One day, out of the blue, he asked me if I could help him with shaving his pubic area again as he felt that I did a great job. Of course I said yes. A couple of days later, it was around the evening time. He was going in for a shower and asked if am free to help him with the shaving. Yes was my answer. He got his gear ready. I told him to wash off with soap once and then shaving would be cleaner. He did. I went in and immediately noticed that he had a hardon. I didn’t comment on it and nonchalantly applied the shaving cream and stared shaving. I could see that his cock was bobbing at times. I of course had to hold it a a few times to get a close shave. I shaved his balls and was shaving his inner thigh area when I noticed and asked if he wanted me to shave his taint. He said sure. I tried but it was kinda tough doing it while he was standing. I told him that he needs to sit on some thing and spread his legs. We went back into the room as we had a bench in there. Locked the door. He laid on the bench, got into position and spread his legs apart. This was a good angle and I was shaving his taint and super turned on to be staring at his asshole. I so wanted to touch it so I casually mentioned that there is hair around his anus. He said shave it off. Damn! My heart jumped with joy. I took my time to apply the shaving cream,, slowly shaving each spot, took every chance to touch his hole. He didn’t flinch at all and seemed very comfortable. I was done. On purpose, I asked him to touch himself and feel the clean shaven taint and asshole. He did and that was so hot watching him touch and feel his hole. I was hoping he would ask for a blowjob but he didn’t. That was disappointing. He jumped into shower and am pretty sure he jerked off.

Some days later, he made plans to hook-up with the girl he had a threesome with. He was really excited to spend 2 days with her. He told me that he probably would come back with wild stories for me. He spent the 2 days with her and got back home. I was eagerly waiting for him to describe his wild getaway. He kept teasing me that he had some wild times with this girl. We had to wait for a couple of more days for some alone time. So it was just the 2 of us at home that night and that was our chance to have our secret conversations. We got the booze and he started telling me all about his wild adventures. This girl knew he was up for some wild times and he tacitly consented to it. The first day he fucked her twice. He described all the positions and the types of foreplay. That evening they were going out for a drink. She said a friend of hers would meet them at the bar. They were at the bar and this guy walks towards them. And that was her friend. Rob was puzzled for a moment and quickly realized that she was setting up a threesome with another guy. He got a little nervous but didn’t wanna ruin things with her so he went along with it. They drank, talked and socialized at the bar. She told Rob that this friend (Jake) was her friend with benefits and that she had many threesomes with him. Rob asked if it was with 2 girls or 2 guys. Jake responded both. The girl took it for granted that Rob would not say no. Both of them checked with Rob if he was cool with it. Rob told them it would be his first time but he doesn’t mind trying it. Jake told him that he was straight and Rob said the same. They all went back to the hotel. Once in there, the girl took total control and guided them with each act. They both took turns in fucking her in different positions. Rob ate her pussy out while she gave him a blowjob and they changed positions. She wanted the guys to cum on her belly. Jake ejaculated first and sprayed it all over her belly. Then Rob sprayed his cum on top of his. After that, they sat around, talked, got back into it again. But this time it was just foreplay. Rob mentioned that at one point she was licking Jake’s asshole and that surprised him. I had so many questions in my head but had to use a filter and asked straight-ish questions only. Jake wanted to stay over the next day as well but he had to get back to work. After he left, Rob and the girl spent time together. He fucked her one more time before he came back home. The kicker was she promised him a foursome with another couple for the next visit.

This whole conversation was such a turn-on for the both of us. At times, Rob was grabbing his cock through his shorts and it was rock hard. He kept saying that talking about the sex was making him super horny. I asked if he wanted a blowjob and he said yes please! Locked the door, took his shorts off, he took his shirt off. He was dripping with pre-cum. I licked it off. Sucked his cock, licked his balls, he fucked my mouth. This time I wasn’t afraid to lick his taint and he didn’t flinch. In fact he seemed like he was enjoying it. I made it seem like I was just licking his balls and the area around it. He seemed very comfortable grabbing my head while I had his cock in my mouth. He finally came inside my mouth and I happily swallowed his load.
I sense that some ass-licking is coming soon. m-m-m-m-m-m
 
I have been intending to share this very relatable, interesting phase of my life for a long time. Work and family life keep me very busy so that is my only excuse for not sharing this sooner.

I have always been a closet bisexual since my teen years.

I lived in a shared 3-bedroom house in med school with 2 guys in each room. The arrangement was that if one of our girlfriends spent the night, then the roommate would sleep in the living room. We were all friendly, had good camaraderie, living a hectic school life so the arrangements were all well-respected.

After the first year, my rommmate moved into a new place with his girlfriend and I got a new roommate. Let’s call the new roommate Rob. Rob and I remained as roommates till we graduated from med school (about 4 years) and a year after that as well, became best friends with a deep emotional connection and more.

Rob was handsome, introvert-ish and very intelligent. He also was a big flirt and dated a few girls through med school and after. When he moved in, he was dating this girl. Since she was still living with her parents, they didn’t need our room to spend nights together. I was single at the time. His GF also became a good friend. In fact, we were a part of a close knit group of friends who always spent time together, going out drinking, movies or studying for exams.

Being roommates and having the same classes, Rob and I got to spend a lot of quality time together. We both partied a little more than others so many times it was just the both of us drinking at a bar or at home and getting into deep-meaningful-philosophical conversations. We also talked about our sex lives with no inhibitions like our jerking off routine, likes/dislikes and more.. But I never dared to tell him (or my other friends) about my sexual orientation. I never sought or hooked up with another guy during those years. I lived a straight life dating a couple of girls. My reasons at the time were fear of being outed and possibly risking any distance between the both of us. Our bond and friendship was more important than anything sexual.

I always wondered, fanatsized about getting sexual with him but there was absolutely no way of that becoming a reality. Med school academically is hard, especially exam phases are tiring and exhausting. We hardly had time to hang out with our girlfriends and it was all understandable as they were going through a similar phase.

Rob and I studied together, discussing, testing each other and we used to get pissed drunk during any break that we could get. One night, we were tired, drunk and having our usual conversation. Rob said his body ached and mentioned that he would try and get a massage from his GF when they meet next. I told him that I could give him a body rub if he was up for it. He was mighty glad and readily accepted it. The only extent that we ever saw each other naked was in our underwear. So he had no inhibitions stripping to his undies for the massage. He laid down in a prone position first and I started rubbing his shoulders, back, legs. Next he was supine and I rubbed his chest, thighs and legs. That was it and he really liked it. I was delighted at the chance of getting to do it.

The massages kept happening more frequently without ever being anything sexual. That went on for sometime. There were times where I noticed his underwear bulge would be more prominent than usual. We also laughed it off a few times. One evening, we woke up after a long nap, lazy, and tired. We went out, grabbed some dinner, had a few drinks. We drank some more after we got back home. We turned off the lights to sleep. After a few minutes, Rob asked if I was up for giving a massage. I was fine with it. I was about to turn the light on and he told me not to. I wondered for a quick second but didn’t think much of it. He stripped to his undies and I was completely clothed as usual. I started rubbing his back, legs. He asked me if I was okay if he took his underwear off as he had a hardon and it was getting uncomfortable laying prone on his hard dick. Why would I say no? He took off his underwear. I could feel my heartbeat getting faster but I acted nonchalant. Then he turned around, I gave him the usual massage, taking extra precaution to avoid bumping into his hardon. That was it.

As time went by, Rob became more comfortable stripping naked during a massage but he always hinted at the lights being off and I never wanted to make him feel uncomfortable. So it always happened in the dark at nights. It was also the best time as other housemates would be sleeping so no danger of getting caught.

One night, while getting ready for a massage, the table lamp was on so I asked if I should to turn it off and he said don’t bother. I wondered for a second but again didn’t want to read much into it. He stripped, I started massaging his back, legs and by then he was also comfortable getting his buttocks massaged. He turned around and there it was! I finally saw his erect cock. I was completely mesmerized but had to act nonchalant. We always talked during the massages but this time he became kinda quiet. I noticed his cock throbbing a few times. I never massaged anywhere near his groin area and always tactfully avoided that area. While massaging his thighs, he told me not to mind his erection, that he was just horny and turned on. He specifically told me not to pay any attention to it. I continued on with the massage. My heartbeat was fast, I was getting hard and I could totally feel this endorphin rush inside my body. I went back to massaging his thighs when he grabbed my hand and pulled it towards his cock. He also muttered if I was okay with it. I said I was fine as long as he was comfortable. He was. So he made me grab his cock. Damn! This peak of excitement has been an unforgettable moment of my life. It was obvious what he wanted so I started to jerk him off until he came. The moments after were just silent, he got up, took a T shirt, cleaned off the cum, turned off the lights, said goodnight and slept off.

The next day was very awkward. He seemed upset and easily irritable. We had classes and a busy day, he spent the night at his GF”s place. The following day, a group of friends went out for a movie, dinner and drinks. He still seemed upset so I just let him be and this was not something we could’ve addressed when others were around.

2 days later, he told me that we need to talk. We went out in the evening and talked. He was angry at himself that he went that far. He blamed it on the alcohol, exam stress and the dry spell that he was going through. He blamed me partly and I kinda defended myself that I did not initiate it. His response was I could’ve stopped it. I told him that I was absolutely comfortable doing it only because of our deep emotional connection and it did not bother me at all. I told him that it seemed very organic for me considering how close we were. He said he didn’t want that to ever happen again. I said fine and we hugged it out. We were back to being the small old friends minus the massages.

That pact didn’t last for long. To be continued…….
My personal opinion is this: it is extremely well-written but boring as hell. I ĺi ed
 
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My third encounter with Rob.

For context, I want to describe Rob’s cock first. It was probably 8+ inches (I never actually measured it and size came up in conversations only), pretty thick, mushroom head, with a very prominent dorsal vein especially when he was hard and uncircumcised.

Rob also had a huge sex drive. Even on days that he had sex with his girlfriend, he would jerk off at least once. His sex drive was definitely more than mine. His girlfriend definitely couldn’t keep up at times as she was a nerd and always on the edge about keeping up with school work. Med school academically does take a toll on you.

One night, we were just having random conversations and he asked me about his foreskin, whether it was a little tight and if I found it hard to retract when I jerked him off. I told him yes, it did seem a little tight when he was hard. I asked if he was able to retract it when he is soft and he responded that he only notices it when he is hard. Otherwise, with some maneuvering he can totally retract it when he is soft. He knew I was uncircumcised too so he asked me if I have any such issues. I told him no. He casually asked if he can see mine to check my foreskin and compare. I had no issues with that. We were both studying to be doctors so we were not prudish. So I pulled my shorts down, held my flaccid cock and retracted my foreskin back and forth a couple of times. He then took his cock out and tried to compare. We concluded that he definitely had some degree of phimosis. He decided to consult with the surgeon the following day.

He went with his girlfriend to see the surgeon. The surgeon confirmed the diagnosis and recommended circumcision. Rob agreed, had the surgery. I visited him on the day of surgery. He wanted to go and stay with his girlfriend for a few days so she could be around for him through his recovery phase. I dropped them off at her place.

3 days later, Rob returned back to our place. After dinner, we were just chilling at home, had a couple of beers and talked. He described how his glans was just getting used to friction and wearing underwear was not comfortable at all. He was also frustrated that his girlfriend was too freaked out to even give him a handjob. We joked around about how he missed out on having a sexually adventurous girl. One time he kinda hinted to her about having a threesome with another girl and that he was craving for one. She was pissed off with him for a few days until he somehow convinced her that it was just a fleeting thought. He talked about how he might just end hooking up with a couple of girls to fulfill his fantasy. I noticed that he was really getting deep into describing his fantasies and what all he would get into during the threesome. It was very obvious that he was super-duper horny. I was totally turned on too with all the sex talk. I pointed at his boner and joked that he was pitching a tent in his shorts. He grabbed it gently and said he was rock hard despite being a little raw near the incision area. He gave me a wicked smile and asked I could help him. I could never say no. Why would I?

He was sitting on a chair. I slipped his shorts off. His foreskin edges were still a bit swollen and his glans was red. I told him maybe it is too soon to do it and let it heal for a couple of more days. He said no way that he can wait for another 2 days. He said just grab the base and be gentle with the motions. I grabbed his cock at the base, slowly started jerking him off. I was watching with a keen eye so that I could keep an even pace and avoid causing any pain. He was absolutely loving it! He started moaning, unusually expressive, saying things like it feels so good, and asked to move to the bed so he could lay flat. He was pushing his buttocks up, his body at times was writhing. He also cupped my hands while I was jerking him off, brushed my hair at times, touched my shoulders and all these movements were new. I was loving it! He wanted a prolonged handjob so he stopped me a couple of times when he was about to come. And then started again. I still remember that his cock was warmer than usual. He also blew a much heavier load. His warm cum dripped all over his cock, my hands, his belly. What an unforgettable feeling that was. He thanked me several times saying he needed this so badly. He also joked if we could do it again in the morning. And yes, we did it again in the morning.
Loving the story.
Only in the US would a circumcision be recommended for slight phimosis!
 
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My next encounter with Rob was the usual blowjob that he asked for one random night and I happily obliged.

Rob officially had a side-chick (Julia) who he was hooking up with whenever he could travel to her town and I was the only one who knew his secret. He went over to spend time with her for a night. After he came back, I asked him about the trip and asked him sheepishly if he got to fuck her brains out. He laughed and said he would tell me some juicy details. I was excited but of course we had to wait for some alone time.

One evening, we finished studying for a test in our room a little earlier than anticipated and decided to have a couple of beers. This was my chance so I told him to tell me all about those juicy details. He was in his jeans and he goes ‘let me first change into my shorts in case I get a hardon and these jeans are tight.’ That sounded hot!

Julia told him that they would be meeting 2 of her friends for some drinks in the evening. It was Jake and another friend (girl). Rob immediately realized that she was possibly setting up the foursome. He asked her and she said that it may happen. So they all met at the bar, drank, talked, flirted. Rob noticed that the new girl was heavily flirting with Jake, rubbing his crotch at times and that Jake had a noticeable bulge. They decided to check into a hotel. Once in the room, the girls started making out and that got both of them excited. They both picked a girl, took their clothes off, started eating out their pussies. The girls then started giving blowjobs, in various positions, they started fucking the girls. Then switched to oral sex again. At one point, Rob noticed that the new girl was blowing Jake and was licking his ass as well. Julia was blowing Rob and slowly but surely went down to his ass, licked it for a bit and then went back for his cock. Then they swapped, fucked the girls and came. They sat around talking, drinking, exchanging crazy sex stories when Rob mentioned that the last time, Julia, Jake and himself had a threesome in the shower. So the new girl said let’s do it again. They went in and started having some wild sex. Rob again noticed Julia licking Jake’s ass during one of the acts. That was that.

The next day, before he came back home, Julia casually told him to keep his asshole shaved and asked if he needed help with that. Rob lied to her and told her that he would ask his girlfriend to do it and that she is used to it. He was actually thinking about me when he told her that.

Of course, we were both rock hard when he finished. I was pretty sure he was going to ask for a blowjob but he did not and I was disappointed. He did that sometimes and that would completely throw me off. I would wonder if it was a straight guy thing where he sometimes wanted to just fantasize about a girl while jerking off instead of a blowjob from me. Or the shame stopping him from asking for a blowjob. I never really got to know so I just would go with his needs. He did ask me to help him with shaving and I said yes.

2 days later, before he jumped into the shower he asked if I had the time to give him a shave. I said sure. I told him that it would be convenient in the bedroom, if he laid down on the bench. So he locked the door. I told him to wash off first. He did that in the shower and then got on the bench for the shave. I shaved his pubic hair, balls, inner thighs and then it was time for the anal area. I asked him to spread his legs, slowly applied the shaving cream. He was rock hard! I took my time in shaving around the hole. After I was done, I told him that I’ll wipe things off with a towel. Before I did that, I told him that I would feel and see if I missed any parts. I gently rubbed his hole. He said ooh, that feels different. I laughed. Then he went into the shower with a rock hard cock and I could see some precum too. It was obvious that he was going to jerk off. He finished his shower, walked out into the room. I noticed that his cock was still erect. He casually asked if I wanted to touch and hold it. Of course I grabbed it and started stroking it. I realized that he didn’t jerk off and wanted me to do it. I told him to lay down on the bed. He did. I started licking off his precum, sucked his cock, licked his balls. He was moaning and I could see that he was loving it. I decided to take a chance and push it a bit further. I licked his taint and slowly started going down to his anus. I pushed his legs up and positioned myself. He didn’t resist. I licked his hole for a bit and went back to his cock. I went for his hole again although I felt that he didn’t seem too keen. I still went there, licked him for a bit, went back to his cock, sucked and he came inside my mouth. I really wanted to ask him about the rimjob but we never really had explicit conversations about me doing things to him so decided not to.
 
My next encounter with Rob was the usual blowjob that he asked for one random night and I happily obliged.

Rob officially had a side-chick (Julia) who he was hooking up with whenever he could travel to her town and I was the only one who knew his secret. He went over to spend time with her for a night. After he came back, I asked him about the trip and asked him sheepishly if he got to fuck her brains out. He laughed and said he would tell me some juicy details. I was excited but of course we had to wait for some alone time.

One evening, we finished studying for a test in our room a little earlier than anticipated and decided to have a couple of beers. This was my chance so I told him to tell me all about those juicy details. He was in his jeans and he goes ‘let me first change into my shorts in case I get a hardon and these jeans are tight.’ That sounded hot!

Julia told him that they would be meeting 2 of her friends for some drinks in the evening. It was Jake and another friend (girl). Rob immediately realized that she was possibly setting up the foursome. He asked her and she said that it may happen. So they all met at the bar, drank, talked, flirted. Rob noticed that the new girl was heavily flirting with Jake, rubbing his crotch at times and that Jake had a noticeable bulge. They decided to check into a hotel. Once in the room, the girls started making out and that got both of them excited. They both picked a girl, took their clothes off, started eating out their pussies. The girls then started giving blowjobs, in various positions, they started fucking the girls. Then switched to oral sex again. At one point, Rob noticed that the new girl was blowing Jake and was licking his ass as well. Julia was blowing Rob and slowly but surely went down to his ass, licked it for a bit and then went back for his cock. Then they swapped, fucked the girls and came. They sat around talking, drinking, exchanging crazy sex stories when Rob mentioned that the last time, Julia, Jake and himself had a threesome in the shower. So the new girl said let’s do it again. They went in and started having some wild sex. Rob again noticed Julia licking Jake’s ass during one of the acts. That was that.

The next day, before he came back home, Julia casually told him to keep his asshole shaved and asked if he needed help with that. Rob lied to her and told her that he would ask his girlfriend to do it and that she is used to it. He was actually thinking about me when he told her that.

Of course, we were both rock hard when he finished. I was pretty sure he was going to ask for a blowjob but he did not and I was disappointed. He did that sometimes and that would completely throw me off. I would wonder if it was a straight guy thing where he sometimes wanted to just fantasize about a girl while jerking off instead of a blowjob from me. Or the shame stopping him from asking for a blowjob. I never really got to know so I just would go with his needs. He did ask me to help him with shaving and I said yes.

2 days later, before he jumped into the shower he asked if I had the time to give him a shave. I said sure. I told him that it would be convenient in the bedroom, if he laid down on the bench. So he locked the door. I told him to wash off first. He did that in the shower and then got on the bench for the shave. I shaved his pubic hair, balls, inner thighs and then it was time for the anal area. I asked him to spread his legs, slowly applied the shaving cream. He was rock hard! I took my time in shaving around the hole. After I was done, I told him that I’ll wipe things off with a towel. Before I did that, I told him that I would feel and see if I missed any parts. I gently rubbed his hole. He said ooh, that feels different. I laughed. Then he went into the shower with a rock hard cock and I could see some precum too. It was obvious that he was going to jerk off. He finished his shower, walked out into the room. I noticed that his cock was still erect. He casually asked if I wanted to touch and hold it. Of course I grabbed it and started stroking it. I realized that he didn’t jerk off and wanted me to do it. I told him to lay down on the bed. He did. I started licking off his precum, sucked his cock, licked his balls. He was moaning and I could see that he was loving it. I decided to take a chance and push it a bit further. I licked his taint and slowly started going down to his anus. I pushed his legs up and positioned myself. He didn’t resist. I licked his hole for a bit and went back to his cock. I went for his hole again although I felt that he didn’t seem too keen. I still went there, licked him for a bit, went back to his cock, sucked and he came inside my mouth. I really wanted to ask him about the rimjob but we never really had explicit conversations about me doing things to him so decided not to.
I need MOOOAAAR
 
Ai meu Deus, eu já chupei um cara hétero e eu gostava de ver o sorriso zombeteiro dele quando ele terminava e gozava na minha boca. Ele sempre me fazia perguntas aleatórias enquanto minha boca ainda estava cheia.

Uma vez eu tentei responder a ele enquanto minha boca ainda estava cheia. Então ele disse: "Cara, ou engole ou cuspa logo."