I consider myself heterosexual, but have often been attracted to male friends. I was a late bloomer and late in losing my virginity (24). So, I really never fully explored my sexuality.....
When I was around 32, I was leading a team at work across many different locations. When I first met George, a 25 year old on our team, I was taken by his intelligence and boyish looks. I got hard just being in the room with him. Over a 2 year period I always found it difficult to be in the same room with him because I would get hard, want to touch him, etc. I recall once on a team offsite in a cabin in the woods he and I arrived the first night alone. When he got out of the car I sensed a emotional connection. But he worked for me, I am married, there was no way.....
When he turned around 27 he got into business school and left the company. He had me come and speak at the school a couple of times. We met up afterwards in my hotel room to talk. I was horny all the time when he as there. I thought about feigning the need for a massage to help my back from all the travel, hoping he would offer to help, but was too timid. I found it interesting that we kept finding ourselves in these awkward arrangements.
During his second year of business school we were both attending the same conference in Boston. He knew I was going and asked to share a room since he was on a student's budget. I said sure. I booked a king room, but told him it was 2 queens. When we both got to the hotel, I lucked out that it was booked full up. When they said "Here is your king", I said, "But we need to queens". The hotel was very upset. George said "Hey, don't worry we can make it work".
I normally wear boxers, but switched to briefs for the trip to help accentuate things. I have a good 8", about 5" soft. With a good size set of balls that really push things out in briefs. After the evening conference session when we returned to the room I turned on the TV, put on a tee shirt and got rid of my pants. I laid towards the foot of the bed watching TV while doing email. He unpacked some things but kept dressed. He sat up towards the other side of the king and worked. I kept wriggling a bit in the bed trying to get in the right position. I made a comment that I was tired traveling because it keeps hurting my lower back...... After about 30 minutes of the suggestions about back pain and having my ass in briefs just a step away to his left, he said "You know, I am pretty good at massage, I can maybe help your back"
I said "Really? You would not be weird with that?"
George said "No"
He came over and sort of straddle my back, slowly rubbing right above my waist. After a few minutes he suggested I take off my shirt so it was out of the way. He went to the bathroom to get some of the lotion to make it a little easier. When he came back he said "do you mind if I take of my pants, I don't want the lotion to get on them".
"No Problem"
I edged up to the foot of the bed a little more to allow my head to drop off the end of the bed. I made sure to let the comforter draw my briefs down about 1/2 way, showing a good part of my crack. George was also wearing briefs and it was clear he had a good thing hidden under them. He went back to work on my back, straddling me just below my ass. He was rubbing me up and down my back, working closer to my now exposed crack. I could feel his hardening cock rub up against my cotton briefs. I was rock hard. The tempo and gyrating started to pick up. We started to work down my legs, towards my crotch, etc. He stepped up and took off his briefs. He had a nice smooth 8 1/2 inches that with not much girth - long and thin.
As he continued the massage he kept pushing his tip up against my briefs and into my hole. I was losing my mind. He took some lube and soaked his dick, pulled the briefs aside and slowly pushed into my asshole. I have never been fucked. I never thought I would be fucked. But at that moment in time I would have done anything in the world to have that cock up my ass. And George obliged. I didn't care that it was bareback. I wanted him to come in my ass.
It hurt, in a good way. Every time the pain increased, he seemed to pause to let my ass relax. Once he was fully in rubbing rather than pushing on my prostate, I could hardly breath. I had precum pouring out of my dick. And still wearing briefs while getting my ass plowed was a huge turn on.
He pulled out his dick, took off my briefs and then pushed back in. He worked me for another 15 mins or so. Working up to a climax that just filled me with a seemingly unbelievable amount of cum. I have never been so turned on in my life. I just quivered there for a while his dick went soft deep in my ass, him laying on my back with our breathing in sync.
As his dick slid out of my ass, I rolled over and kissed him on the lips. We had a passionate kiss for a bit. A few tears of pleasure rolled off his face and hit me on the cheek. We just held each other until are bodies were at ease.
We kept going all evening, but this story is getting a bit long for this post. Around 2 am we were talking (After he went down on me and I fucked him, also bare back). He said he had been hot for me every since we first met. He did not know why, but he constantly fantasized about just what happened that evening.
We remain good friends. We hook up now and again. Each time is just as hot. We both love women, but have this special time when we can.
When I was around 32, I was leading a team at work across many different locations. When I first met George, a 25 year old on our team, I was taken by his intelligence and boyish looks. I got hard just being in the room with him. Over a 2 year period I always found it difficult to be in the same room with him because I would get hard, want to touch him, etc. I recall once on a team offsite in a cabin in the woods he and I arrived the first night alone. When he got out of the car I sensed a emotional connection. But he worked for me, I am married, there was no way.....
When he turned around 27 he got into business school and left the company. He had me come and speak at the school a couple of times. We met up afterwards in my hotel room to talk. I was horny all the time when he as there. I thought about feigning the need for a massage to help my back from all the travel, hoping he would offer to help, but was too timid. I found it interesting that we kept finding ourselves in these awkward arrangements.
During his second year of business school we were both attending the same conference in Boston. He knew I was going and asked to share a room since he was on a student's budget. I said sure. I booked a king room, but told him it was 2 queens. When we both got to the hotel, I lucked out that it was booked full up. When they said "Here is your king", I said, "But we need to queens". The hotel was very upset. George said "Hey, don't worry we can make it work".
I normally wear boxers, but switched to briefs for the trip to help accentuate things. I have a good 8", about 5" soft. With a good size set of balls that really push things out in briefs. After the evening conference session when we returned to the room I turned on the TV, put on a tee shirt and got rid of my pants. I laid towards the foot of the bed watching TV while doing email. He unpacked some things but kept dressed. He sat up towards the other side of the king and worked. I kept wriggling a bit in the bed trying to get in the right position. I made a comment that I was tired traveling because it keeps hurting my lower back...... After about 30 minutes of the suggestions about back pain and having my ass in briefs just a step away to his left, he said "You know, I am pretty good at massage, I can maybe help your back"
I said "Really? You would not be weird with that?"
George said "No"
He came over and sort of straddle my back, slowly rubbing right above my waist. After a few minutes he suggested I take off my shirt so it was out of the way. He went to the bathroom to get some of the lotion to make it a little easier. When he came back he said "do you mind if I take of my pants, I don't want the lotion to get on them".
"No Problem"
I edged up to the foot of the bed a little more to allow my head to drop off the end of the bed. I made sure to let the comforter draw my briefs down about 1/2 way, showing a good part of my crack. George was also wearing briefs and it was clear he had a good thing hidden under them. He went back to work on my back, straddling me just below my ass. He was rubbing me up and down my back, working closer to my now exposed crack. I could feel his hardening cock rub up against my cotton briefs. I was rock hard. The tempo and gyrating started to pick up. We started to work down my legs, towards my crotch, etc. He stepped up and took off his briefs. He had a nice smooth 8 1/2 inches that with not much girth - long and thin.
As he continued the massage he kept pushing his tip up against my briefs and into my hole. I was losing my mind. He took some lube and soaked his dick, pulled the briefs aside and slowly pushed into my asshole. I have never been fucked. I never thought I would be fucked. But at that moment in time I would have done anything in the world to have that cock up my ass. And George obliged. I didn't care that it was bareback. I wanted him to come in my ass.
It hurt, in a good way. Every time the pain increased, he seemed to pause to let my ass relax. Once he was fully in rubbing rather than pushing on my prostate, I could hardly breath. I had precum pouring out of my dick. And still wearing briefs while getting my ass plowed was a huge turn on.
He pulled out his dick, took off my briefs and then pushed back in. He worked me for another 15 mins or so. Working up to a climax that just filled me with a seemingly unbelievable amount of cum. I have never been so turned on in my life. I just quivered there for a while his dick went soft deep in my ass, him laying on my back with our breathing in sync.
As his dick slid out of my ass, I rolled over and kissed him on the lips. We had a passionate kiss for a bit. A few tears of pleasure rolled off his face and hit me on the cheek. We just held each other until are bodies were at ease.
We kept going all evening, but this story is getting a bit long for this post. Around 2 am we were talking (After he went down on me and I fucked him, also bare back). He said he had been hot for me every since we first met. He did not know why, but he constantly fantasized about just what happened that evening.
We remain good friends. We hook up now and again. Each time is just as hot. We both love women, but have this special time when we can.
