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Gay Stories
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Bi-Sexual Male / 49
Losing My Anal Virginity
I was very curious about gay sex as a teenager. I had a girlfriend in high school and had sex with her but my curiosity for dick has me questioning my sexuality. Then one summer day I took my girlfriends anal virginity at her house when he parents went on vacation. See my dick sink into her tight butthole. See the expression on her face. It made my hole tingle.
I worked at a hardware store during high school. A Mature older guy named Fred owned it. He was pretty good looking too. I’m sure he caught me staring at his bulge or staring at him when he changed his pants there. He had a nice bulge in his underwear. Was no hiding that bulge in tighty whities.
Then one day in his office he asked me about my girlfriend. I said everything is going fine. Then he got up and locked his office door. He undid his belt and jeans and let them fall to his ankles. He reached in his tighty whities and pulled out a nice hunk of meat! At the time it looked huge to me but he was average I’d say. Circumcised and very hairy. He said my wife doesn’t put out often anymore so I was curious if you wanted to help. I got right to my knees and started sucking him off. He shot rope after rope of cum all over my face. He had a huge load! As his cock was still dripping cum he put it back in his tighty whities as he gave me a towel to clean my face off.
Things were kinda awkward for me at work after that. I wanted more but did t know how to ask. Till one day about a week later Fred comes to the store around closing time as usual. He locks the front door and puts the closed sign up. As he’s doing that I’m pulling the money out of the register. He walks down an isle and comes back with Vaseline in his hand! I had a feeling of what was about to cum. He said finish counting then come to my office.
When I walked in his office his jeans and tighty whities were in the chain. He told me to strip. I took my jeans and tighty whities off and tossed them in the other chair. I told him I was a virgin and he said I know. I bent over his desk where he put some Vaseline on my butthole and his dick. Slowly he penetrated me.
It hurt! Won’t lie. I was moaning and he was telling me to breathe and relax. After a few minutes things felt much better and he was finally in my rectum. He started to fuck me. My head was overwhelmed with feels and emotions. I was finally experiencing what I’ve wanted to try. For 5 minutes Fred was fucking my ass till he swelled up real big and let out moans. He was cumming in my butt.
Once finished abd he pulled out he said sorry I should had told you that I cum inside. Said he hated to pull out. I wasn’t worried at all! But boy was my hole feeling funny! We used the shower in his office bathroom to clean up then got dressed. He told me not to be surprised if cum leaks out into my underwear. Glad he told me that because cum was dripping into my tighty whities on my walk home.
The following morning my butthole was so sore! It hurt but it felt great to me. I fucked my girlfriend that day and came pretty quick thinking about the dick I had taken. So from then on Fred would fuck me once or twice a week usually. Many times he fucked me while the store was open and I’d have to wait on customers inbetween getting fucked or with cum in my butt.
But once I moved away to college the fucking stopped. It’s not until now at 49 that I got a craving for dick again. My wife is well aware of my past sexual experiences too.
I worked at a hardware store during high school. A Mature older guy named Fred owned it. He was pretty good looking too. I’m sure he caught me staring at his bulge or staring at him when he changed his pants there. He had a nice bulge in his underwear. Was no hiding that bulge in tighty whities.
Then one day in his office he asked me about my girlfriend. I said everything is going fine. Then he got up and locked his office door. He undid his belt and jeans and let them fall to his ankles. He reached in his tighty whities and pulled out a nice hunk of meat! At the time it looked huge to me but he was average I’d say. Circumcised and very hairy. He said my wife doesn’t put out often anymore so I was curious if you wanted to help. I got right to my knees and started sucking him off. He shot rope after rope of cum all over my face. He had a huge load! As his cock was still dripping cum he put it back in his tighty whities as he gave me a towel to clean my face off.
Things were kinda awkward for me at work after that. I wanted more but did t know how to ask. Till one day about a week later Fred comes to the store around closing time as usual. He locks the front door and puts the closed sign up. As he’s doing that I’m pulling the money out of the register. He walks down an isle and comes back with Vaseline in his hand! I had a feeling of what was about to cum. He said finish counting then come to my office.
When I walked in his office his jeans and tighty whities were in the chain. He told me to strip. I took my jeans and tighty whities off and tossed them in the other chair. I told him I was a virgin and he said I know. I bent over his desk where he put some Vaseline on my butthole and his dick. Slowly he penetrated me.
It hurt! Won’t lie. I was moaning and he was telling me to breathe and relax. After a few minutes things felt much better and he was finally in my rectum. He started to fuck me. My head was overwhelmed with feels and emotions. I was finally experiencing what I’ve wanted to try. For 5 minutes Fred was fucking my ass till he swelled up real big and let out moans. He was cumming in my butt.
Once finished abd he pulled out he said sorry I should had told you that I cum inside. Said he hated to pull out. I wasn’t worried at all! But boy was my hole feeling funny! We used the shower in his office bathroom to clean up then got dressed. He told me not to be surprised if cum leaks out into my underwear. Glad he told me that because cum was dripping into my tighty whities on my walk home.
The following morning my butthole was so sore! It hurt but it felt great to me. I fucked my girlfriend that day and came pretty quick thinking about the dick I had taken. So from then on Fred would fuck me once or twice a week usually. Many times he fucked me while the store was open and I’d have to wait on customers inbetween getting fucked or with cum in my butt.
But once I moved away to college the fucking stopped. It’s not until now at 49 that I got a craving for dick again. My wife is well aware of my past sexual experiences too.
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