Lost My Virginity to my Boss

[free_shoutouts]

I have read many stories on this forum for a while but never posted one of my experiences before. Well here is mine, just thought I'd share, may be boring to some but it is what it is.

I am in my mid-20's, never had sex before, or really done any sexual experience before. I am technically bisexual but mainly into guys and have never dated or even kissed anyone before (but not from lack of trying lol). Part of me has always had that mentality of wanting all those moments with someone special. But as I've gotten older I realized, might as well get it over with but at least do it with someone at least caring and hopefully with someone I know. I genuinely hate dating or hookup apps, not because of the people just not my thing. I'd say I'm 70% masculine mentally, but physically I look like a twink (I'm athletic but just too lazy to work out post my athletic career).

I always thought I was a bottom because of my physical size and my dick (I'm slightly below average but that's fine with me as long as I can jerk it, it also curves up so idk if I can even fuck a person with it). But I bought a sex toy and fucking it feels so nice. Regardless I always wanted to try bottoming in person, using dildos never truly did it for me.

So enough about my insecurities lol, I started a job two years ago and it has been pretty good. Nice coworkers, lots to do, and a safe space. Personally I never thought of anyone there sexually in my mind, they were all just coworkers or friends to me. But about a year in, for some reason, one of my bosses was just constantly on my mind. Like I said, I never thought about him that way but looking at him more and more, it gave me a nice feeling down there. He was cool, we would occasionally get lunch together during work, had some nice conversations and has similar humor to me.

So he is a white man, in his mid-40's, definitely old enough to legally be my dad but whatever, he did have a bit of a dad bod, meaty arms that weren't necessarily muscular but wasn't flabby, had a bit of a beer gut but I liked that. Whenever we talked and I can see his whole body, when he looked away I would take a look at his crotch to see if he had a boner or at least see if he was packing. Unfortunately he's the kind of guy who is between sizes so wears clothes a little too big for him. But my guesses was that he was packing, probably around 7". He also wore undershirts too so I can never see his nipples poking out, but that would have ended me had I could see them.

Anyways, he was divorced with a kid around half my age, and although the idea of dating this man would be cool, I didn't want to interfere with his kid's life. But he's a single man who probably had a whole lot of sex with his ex-wife or at least beat his meat a lot based on the sexual humor he always says. Personally, I thought, this man says sex jokes all the time and isn't dating, even though he's straight, he'll be desperate enough to put his dick in any type of hole. Could be a win win situation.

After months of constantly thinking of this man, I finally told myself just go for it. Like it'll be fucking weird to ask but he seems cool enough that even if he was like fuck no, he wouldn't rat me out or disown me as a friend.

So one Friday before the weekend, we went out to lunch. I was flipping nervous. Kept the lunch talk casual before I started to ask him about his sex life. We never talked about that kind of thing before but I felt like I had to ease my way into the asking part. The conversation was a little awkward on both ends, but he pointed out he hasn't really had sex since his divorce which was years ago. He also hadn't really talked to any other female romantically since then as well.

The conversation and lunch pretty much ended there and threw our trash away and headed to the car. I drove so I was in the passenger seat and once we got into the car I was so nervous. I basically just ended blurting out "Since you haven't done anything in a while, can I suck your dick?" The look he gave me was definitely a WTF kind of look and I for sure cringed. He said "Dude, are you serious?" in confusion. I was pretty honest, "Yeah like I just thought I'd ask, I kind of want to try and like I won't tell anyone, just stays between you and me". He asked me if I was gay and I explained what I was and I told him "Can I try it, like after a minute you don't like it we can stop, this doesn't mean anything to me I just thought out of everyone you might want it and idk". At first he said no, so I apologized. We kind of sat quietly for a minute and then he kind of looked and me said, "you really want to try it?". I nodded and he said "okay fine, we'll try it but if it gets too weird then I'm stopping you."

I told him okay and made him slide the passenger seat as far back as he could. I hopped into the leg room area and luckily I'm small and flexible enough to fit there between his legs. Even though I was nervous I tried to play it cool and laugh to make it feel less awkward. He definitely had a straight man mentality of looking upset this was happening but let it happen anyways.

Sitting between his legs he started to unbuckle his pants as I pulled his zipper down. We tried to pull his boxer briefs down but doing it in a car isn't ideal. So he got up a little and pulled his pants and briefs down above his knees. I was so focused on getting his pants down that I didn't see his junk unveiled but when I looked up and saw his cock and balls, it looked so nice. He was soft and looked small at first (bigger than me for sure though) but even when he was soft, his dick was thick. My mouth was small so that I knew was going to be a problem. I looked at it for a few seconds and he was looking away because he didn't want to think of being sucked off by a guy and I went for it.

I put his soft dick in my mouth and closed my eyes and put all of it in my mouth while I could before he gets hard. I went back and forward on it at a decent pace, not slow but not fast. The only thoughts in my head were wow I'm giving my first blowjob and I hope he likes it. I kept going and around what I thought was a minute, he didn't stop me. After another minute I can feel him getting harder, at a rate he got really hard. He was definitely a grower cause that what actually turned out to be 7" thick cock was way big for my mouth. I couldn't fit the whole thing in there and I knew I would gag if I tried the whole thing. I could pretty much barely get half in my mouth. But I kept sucking that thing. I opened my eyes and looked up while holding his dick and licked from bottom to top and he had his eyes closed looking ready to moan.

I took his hand and he tried to snap back thinking I was going to hold it. But I grabbed it again and he let me as I put it on the back of my head. After a bit he would bob my head back and forward. At some points I gagged cause his dick was so thick. I took a quick breather and went right back to sucking. Sometimes I tried deep throating his dick and gagged and teared up a bit but then continued to suck. I wasn't paying attention just sucking and then he hastily pulled my head back and said "fuck I'm gonna cum". He grabbed his dick and stroked it and told me to open my mouth. I personally wanted him to nut while I sucked him dry but it all happened pretty quick. He groaned a bit as he released his cum, half missed and ended on the bottom of the seat, but a little got in my mouth and some on my nose and around my lips. Once he stopped I moved his hand and sucked the head of his cock to get any remainder of cum. He didn't want to at first and I could tell he was sensitive after busting but I still went for it to a point he said to stop. I backed off and wiped the cum off my face and try to lick it all but there was a lot so I wiped the rest with a napkin.

We didn't say anything while we cleaned up and then all he said after was that we need to head back to work. I tried to make conversation but it was a little awkward for both. I asked him if was good, he said it was alright. Personally, I'll take that. But I joked that it was the best he ever had, he smirked.

I have more to the story, just have to do a part 2 when I have time

 

[jeez_00]

cool!

 

[justhereforaday]

I have read many stories on this forum for a while but never posted one of my experiences before. Well here is mine, just thought I'd share, may be boring to some but it is what it is.

I am in my mid-20's, never had sex before, or really done any sexual experience before. I am technically bisexual but mainly into guys and have never dated or even kissed anyone before (but not from lack of trying lol). Part of me has always had that mentality of wanting all those moments with someone special. But as I've gotten older I realized, might as well get it over with but at least do it with someone at least caring and hopefully with someone I know. I genuinely hate dating or hookup apps, not because of the people just not my thing. I'd say I'm 70% masculine mentally, but physically I look like a twink (I'm athletic but just too lazy to work out post my athletic career).

I always thought I was a bottom because of my physical size and my dick (I'm slightly below average but that's fine with me as long as I can jerk it, it also curves up so idk if I can even fuck a person with it). But I bought a sex toy and fucking it feels so nice. Regardless I always wanted to try bottoming in person, using dildos never truly did it for me.

So enough about my insecurities lol, I started a job two years ago and it has been pretty good. Nice coworkers, lots to do, and a safe space. Personally I never thought of anyone there sexually in my mind, they were all just coworkers or friends to me. But about a year in, for some reason, one of my bosses was just constantly on my mind. Like I said, I never thought about him that way but looking at him more and more, it gave me a nice feeling down there. He was cool, we would occasionally get lunch together during work, had some nice conversations and has similar humor to me.

So he is a white man, in his mid-40's, definitely old enough to legally be my dad but whatever, he did have a bit of a dad bod, meaty arms that weren't necessarily muscular but wasn't flabby, had a bit of a beer gut but I liked that. Whenever we talked and I can see his whole body, when he looked away I would take a look at his crotch to see if he had a boner or at least see if he was packing. Unfortunately he's the kind of guy who is between sizes so wears clothes a little too big for him. But my guesses was that he was packing, probably around 7". He also wore undershirts too so I can never see his nipples poking out, but that would have ended me had I could see them.

Anyways, he was divorced with a kid around half my age, and although the idea of dating this man would be cool, I didn't want to interfere with his kid's life. But he's a single man who probably had a whole lot of sex with his ex-wife or at least beat his meat a lot based on the sexual humor he always says. Personally, I thought, this man says sex jokes all the time and isn't dating, even though he's straight, he'll be desperate enough to put his dick in any type of hole. Could be a win win situation.

After months of constantly thinking of this man, I finally told myself just go for it. Like it'll be fucking weird to ask but he seems cool enough that even if he was like fuck no, he wouldn't rat me out or disown me as a friend.

So one Friday before the weekend, we went out to lunch. I was flipping nervous. Kept the lunch talk casual before I started to ask him about his sex life. We never talked about that kind of thing before but I felt like I had to ease my way into the asking part. The conversation was a little awkward on both ends, but he pointed out he hasn't really had sex since his divorce which was years ago. He also hadn't really talked to any other female romantically since then as well.

The conversation and lunch pretty much ended there and threw our trash away and headed to the car. I drove so I was in the passenger seat and once we got into the car I was so nervous. I basically just ended blurting out "Since you haven't done anything in a while, can I suck your dick?" The look he gave me was definitely a WTF kind of look and I for sure cringed. He said "Dude, are you serious?" in confusion. I was pretty honest, "Yeah like I just thought I'd ask, I kind of want to try and like I won't tell anyone, just stays between you and me". He asked me if I was gay and I explained what I was and I told him "Can I try it, like after a minute you don't like it we can stop, this doesn't mean anything to me I just thought out of everyone you might want it and idk". At first he said no, so I apologized. We kind of sat quietly for a minute and then he kind of looked and me said, "you really want to try it?". I nodded and he said "okay fine, we'll try it but if it gets too weird then I'm stopping you."

I told him okay and made him slide the passenger seat as far back as he could. I hopped into the leg room area and luckily I'm small and flexible enough to fit there between his legs. Even though I was nervous I tried to play it cool and laugh to make it feel less awkward. He definitely had a straight man mentality of looking upset this was happening but let it happen anyways.

Sitting between his legs he started to unbuckle his pants as I pulled his zipper down. We tried to pull his boxer briefs down but doing it in a car isn't ideal. So he got up a little and pulled his pants and briefs down above his knees. I was so focused on getting his pants down that I didn't see his junk unveiled but when I looked up and saw his cock and balls, it looked so nice. He was soft and looked small at first (bigger than me for sure though) but even when he was soft, his dick was thick. My mouth was small so that I knew was going to be a problem. I looked at it for a few seconds and he was looking away because he didn't want to think of being sucked off by a guy and I went for it.

I put his soft dick in my mouth and closed my eyes and put all of it in my mouth while I could before he gets hard. I went back and forward on it at a decent pace, not slow but not fast. The only thoughts in my head were wow I'm giving my first blowjob and I hope he likes it. I kept going and around what I thought was a minute, he didn't stop me. After another minute I can feel him getting harder, at a rate he got really hard. He was definitely a grower cause that what actually turned out to be 7" thick cock was way big for my mouth. I couldn't fit the whole thing in there and I knew I would gag if I tried the whole thing. I could pretty much barely get half in my mouth. But I kept sucking that thing. I opened my eyes and looked up while holding his dick and licked from bottom to top and he had his eyes closed looking ready to moan.

I took his hand and he tried to snap back thinking I was going to hold it. But I grabbed it again and he let me as I put it on the back of my head. After a bit he would bob my head back and forward. At some points I gagged cause his dick was so thick. I took a quick breather and went right back to sucking. Sometimes I tried deep throating his dick and gagged and teared up a bit but then continued to suck. I wasn't paying attention just sucking and then he hastily pulled my head back and said "fuck I'm gonna cum". He grabbed his dick and stroked it and told me to open my mouth. I personally wanted him to nut while I sucked him dry but it all happened pretty quick. He groaned a bit as he released his cum, half missed and ended on the bottom of the seat, but a little got in my mouth and some on my nose and around my lips. Once he stopped I moved his hand and sucked the head of his cock to get any remainder of cum. He didn't want to at first and I could tell he was sensitive after busting but I still went for it to a point he said to stop. I backed off and wiped the cum off my face and try to lick it all but there was a lot so I wiped the rest with a napkin.

We didn't say anything while we cleaned up and then all he said after was that we need to head back to work. I tried to make conversation but it was a little awkward for both. I asked him if was good, he said it was alright. Personally, I'll take that. But I joked that it was the best he ever had, he smirked.

I have more to the story, just have to do a part 2 when I have time

Very hot! Part 2 pls! Did he fuck you in the end?

 

[free_shoutouts]

Here is I guess my part 2, what happened later. Sorry if this is too much dialogue, just going off of what I remember.

Following our first encounter, not sure if it was a coincidence or on purpose, but we didn't see much of each other at work the following week. Pretty sure we were both really busy with work and outside stuff but timing just seemed weird. Personally I didn't want things to be weird, I wasn't actively looking to do sexual things with him, just wanted things to still feel normal after it happened.

Towards the end of the next week, things got less busy at work. I decided to head over to him to see if he wanted to grab lunch. He sure in a normal tone so that was a good sign. We drove to a food place, which was pretty empty so once we ordered and got our food, we sat a table with pretty much no one around us.

The conversation was normal, work stuff, life stuff. I didn't want to bring our experience up but I did and I asked him, "So, was I good at you know..." I looked around to make sure no one was around then proceeded, "sucking you off?" He just gave me a look that translated to "are you serious" but with a smirk. He didn't say anything at first but then said "it was fine". I asked if he would ever do it again and he was like "I didn't think you were this horny of a person". I wasn't asking because I wanted to do it again, but was just curious. I said "I'm not I just wanted to know, like I'm not trying to make you anything, sometimes I just wondered." He said okay and jokingly rolled his eyes and didn't answer the question. The conversation changed as we started to pack up to leave.

We got into the car and before he turned on tried to turn on the car, I jokingly told him "Can't believe you think I'm so horny, I bet you are just as horny as a person as me". He denied it, so I slowly grazed my hand towards his crotch. He gave me that are you serious look with the smirk and didn't bother to stop me. I put my hand on his jeans to feel his dick and he was hard. Probably not fully but at least semi hard. I said "see you are just as horny." He claims it wasn't from our conversations but I don't know what I believe.

I asked him "so want to do it again?"

He said, "seriously, you're going to ask that?" I hate that I was getting too comfortable talking about this since I'm not usually this kind of person. I said "what? like I said this doesn't mean anything. How about we just jerk off together." He didn't say anything and looked away.

I definitely got horny as of recently and started to touch myself. I pulled my zipper down and unbuckled my belt and pulled my hard cock out. He looked and softly laughed at me calling me small. Like I said before, I don't care about my size, and hearing him laugh made me think he was a little bit comfortable. I said "come on, just blow off some steam". He again didn't say anything so I leaned over the center console and unbuckled and unzipped him, still just looking at me and not stopping me.

I grabbed his semi hard cock and stroked it slowly and made eye contact with him and he pulled my hand off. He grabbed his own cock and touched it a bit. I kind of smiled at him knowing that he wasn't saying no to this. I asked so "how about this, you let me suck you off if I can cum before you?" He thought it wasn't fair, since I was harder than him. I told him he could watch porn and I'll get soft to make it more fair.

He pulled out his phone and looked up some porn because he claims he didn't want to get sucked off again so he was trying to cum first. His videos started and he started jerking. While he was getting set up, I couldn't look at him because I knew I would get a boner just by seeing his dick. But once I started, it was go time. I know most people are embarrassed of cumming quickly, but honestly I like it, feels nice just to let it go. And even though he got to watch porn, looking at him is the only porn I needed.

His eyes were down on his phone while he stroked his thick cock. He was stroking fast trying to win. But so was I. I can see the concentration on his face almost like he was biting his lip. I just stared at him and his big dick and imagined me leaning over trying to stuff the whole thing in my mouth. Not going to lie, it was probably only 2 minutes from being soft, I announced I was cumming.

It was so hot watching him stroke, I didn't know how big my load would be, but I shot my upward curved dick with a few skinny strands of cum up towards my belly button trying not to get it on my sweatshirt. He said "don't get it on my seats". I smiled and grabbed a napkin we had from lunch and cleaned up. He sort of stopped stroking, hand still around his cock doing real slow strokes. I leaned over and said "I win".

He did another eye roll and let go of his cock. I smiled at him and leaned over again this time, more over the center console and moved my head closer to his cock head. I looked at him while I did it, in a way to almost guilt him for losing but also to remind him that I was about to suck his dick. I stayed looking at him even though he tried to look away as I put his downgraded semi hard cock's head in my mouth. I sucked only the tip for a little bit. He needed to adjust a bit as he was uncomfortable in his seat and when he moved it thrusted his cock more into my mouth.

I gagged a little and he laughed and said "my bad". I gave him the are you serious look back to him like he had to me many times that day. I stroked his cock and started to go to town on his cock. His thick dick stuffed my mouth and he made sure of it. He wasn't rough but wasn't gentle as he put his head on the back of my head like last time. This time he actually started to fuck my mouth a bit, and that was so hot. I heard him moan a bit when he did that.

This felt like a long blowjob but it tasted so good. I was sucking while stroking his shaft and playing with his balls a bit. He pulled me off and said he was coming soon. I told him let me suck you until you cum. So he grabbed my short hair and started thrusting again, and he really felt like he was into this. He kept fucking my mouth until I heard him moan like crazy and his cum shot in my mouth. I had never knew how it was going to feel but I could feel his cum in the back of my mouth. Each and every shot. He came back to reality as I pulled off and swallowed his cum. I went back to do a little clean up work on his dick to get the last remaining drips. He grabbed the last napkin, tapped my head to get off and wiped his cock and I looked at him and he was sweating a bit from this.

I laughed at him and he just looked and smirked. He laughed and said okay okay time to go back. It was weird to say this felt so casual now.

More stuff happens later, I still feel weird writing this stuff but a lot of emotion comes from this lol. I'll write more later.

 

[justhereforaday]

Here is I guess my part 2, what happened later. Sorry if this is too much dialogue, just going off of what I remember.

Following our first encounter, not sure if it was a coincidence or on purpose, but we didn't see much of each other at work the following week. Pretty sure we were both really busy with work and outside stuff but timing just seemed weird. Personally I didn't want things to be weird, I wasn't actively looking to do sexual things with him, just wanted things to still feel normal after it happened.

Towards the end of the next week, things got less busy at work. I decided to head over to him to see if he wanted to grab lunch. He sure in a normal tone so that was a good sign. We drove to a food place, which was pretty empty so once we ordered and got our food, we sat a table with pretty much no one around us.

The conversation was normal, work stuff, life stuff. I didn't want to bring our experience up but I did and I asked him, "So, was I good at you know..." I looked around to make sure no one was around then proceeded, "sucking you off?" He just gave me a look that translated to "are you serious" but with a smirk. He didn't say anything at first but then said "it was fine". I asked if he would ever do it again and he was like "I didn't think you were this horny of a person". I wasn't asking because I wanted to do it again, but was just curious. I said "I'm not I just wanted to know, like I'm not trying to make you anything, sometimes I just wondered." He said okay and jokingly rolled his eyes and didn't answer the question. The conversation changed as we started to pack up to leave.

We got into the car and before he turned on tried to turn on the car, I jokingly told him "Can't believe you think I'm so horny, I bet you are just as horny as a person as me". He denied it, so I slowly grazed my hand towards his crotch. He gave me that are you serious look with the smirk and didn't bother to stop me. I put my hand on his jeans to feel his dick and he was hard. Probably not fully but at least semi hard. I said "see you are just as horny." He claims it wasn't from our conversations but I don't know what I believe.

I asked him "so want to do it again?"

He said, "seriously, you're going to ask that?" I hate that I was getting too comfortable talking about this since I'm not usually this kind of person. I said "what? like I said this doesn't mean anything. How about we just jerk off together." He didn't say anything and looked away.

I definitely got horny as of recently and started to touch myself. I pulled my zipper down and unbuckled my belt and pulled my hard cock out. He looked and softly laughed at me calling me small. Like I said before, I don't care about my size, and hearing him laugh made me think he was a little bit comfortable. I said "come on, just blow off some steam". He again didn't say anything so I leaned over the center console and unbuckled and unzipped him, still just looking at me and not stopping me.

I grabbed his semi hard cock and stroked it slowly and made eye contact with him and he pulled my hand off. He grabbed his own cock and touched it a bit. I kind of smiled at him knowing that he wasn't saying no to this. I asked so "how about this, you let me suck you off if I can cum before you?" He thought it wasn't fair, since I was harder than him. I told him he could watch porn and I'll get soft to make it more fair.

He pulled out his phone and looked up some porn because he claims he didn't want to get sucked off again so he was trying to cum first. His videos started and he started jerking. While he was getting set up, I couldn't look at him because I knew I would get a boner just by seeing his dick. But once I started, it was go time. I know most people are embarrassed of cumming quickly, but honestly I like it, feels nice just to let it go. And even though he got to watch porn, looking at him is the only porn I needed.

His eyes were down on his phone while he stroked his thick cock. He was stroking fast trying to win. But so was I. I can see the concentration on his face almost like he was biting his lip. I just stared at him and his big dick and imagined me leaning over trying to stuff the whole thing in my mouth. Not going to lie, it was probably only 2 minutes from being soft, I announced I was cumming.

It was so hot watching him stroke, I didn't know how big my load would be, but I shot my upward curved dick with a few skinny strands of cum up towards my belly button trying not to get it on my sweatshirt. He said "don't get it on my seats". I smiled and grabbed a napkin we had from lunch and cleaned up. He sort of stopped stroking, hand still around his cock doing real slow strokes. I leaned over and said "I win".

He did another eye roll and let go of his cock. I smiled at him and leaned over again this time, more over the center console and moved my head closer to his cock head. I looked at him while I did it, in a way to almost guilt him for losing but also to remind him that I was about to suck his dick. I stayed looking at him even though he tried to look away as I put his downgraded semi hard cock's head in my mouth. I sucked only the tip for a little bit. He needed to adjust a bit as he was uncomfortable in his seat and when he moved it thrusted his cock more into my mouth.

I gagged a little and he laughed and said "my bad". I gave him the are you serious look back to him like he had to me many times that day. I stroked his cock and started to go to town on his cock. His thick dick stuffed my mouth and he made sure of it. He wasn't rough but wasn't gentle as he put his head on the back of my head like last time. This time he actually started to fuck my mouth a bit, and that was so hot. I heard him moan a bit when he did that.

This felt like a long blowjob but it tasted so good. I was sucking while stroking his shaft and playing with his balls a bit. He pulled me off and said he was coming soon. I told him let me suck you until you cum. So he grabbed my short hair and started thrusting again, and he really felt like he was into this. He kept fucking my mouth until I heard him moan like crazy and his cum shot in my mouth. I had never knew how it was going to feel but I could feel his cum in the back of my mouth. Each and every shot. He came back to reality as I pulled off and swallowed his cum. I went back to do a little clean up work on his dick to get the last remaining drips. He grabbed the last napkin, tapped my head to get off and wiped his cock and I looked at him and he was sweating a bit from this.

I laughed at him and he just looked and smirked. He laughed and said okay okay time to go back. It was weird to say this felt so casual now.

More stuff happens later, I still feel weird writing this stuff but a lot of emotion comes from this lol. I'll write more later.

You write the retelling in such a real and visual feeling way. It feels so authentic and hot... I want him to get the courage to fuck you : ) If he hasn't already...

 

[KeepSecret]

Its soo nice to read such a candid story and think on the details of how it happened. I really want to know more.

 

[jjdiamond]

Can’t wait for the next part!

 

[Mikurakof]

Can't wait for part 3

 

[Winteralex]

I need more

 

[freecmax1]

Wow! Need More!

 

[Erlonjris]

I need part 3

 

[alexandro95]

Need pt 3

 

[nikkel]

Ahhh need part 3 and also I need him to fuck you

 

[QuietPrelude]

No anal?

 

[NarutoClark]

Waiting for 3rd part...

 

[EricGarcia1]

Yum

 

[anime_fan27]

No part 3??