Not what I expected
One of my friends just got destroyed in a horrible divorce. His wife took everything. God I’ve never seen a guy so down in my life. So Out for a beer and a eventually back to his place for shoulder to cry on. We were watching porn when I asked him if there was any way that I could help him. He blushed and said nothing but thanks for being such a good friend but he quietly wondered how serious I was. He’s a good guy so I mentioned that wanted to help. Then it got weird.
He reaches behind the couch and hands me a bag full of clothes and asks me to try them on. I look and it’s a blonde wig, bra and panties set amazingly in my size. He’s basically begging me to put them on because it would actually make him feel better. He was so down that I felt that if this would make him better what could it hurt? So I reluctantly agreed. Bad idea.
I check myself out in the bathroom mirror fully dressed and I had to admit I actually looked good. I came out to model for him and he asked me to sit on the couch while he got me another beer. I was pretty drUnk. He came back and kinda surprised me. He had sissy husband crossdress porn on the television and it was kinda hot, causing my erection. He gave me my beer then sat next to me on the couch and commented about my erect penis through the silk panties, god they were comfortable. He then mentioned my pert nipples but instead of just commenting, he moved his hand over and started twitching them before he began feeling me up. I finally understand how women feel when suddenly a guys hand is in their bra
I’m super uncomfortable at this point as this guy who I thought was my friend is pawing me everywhere, including “accidentally” stroking my super erect rod. From this point on he is under the assumption that I’m an actual woman really attacking my swelling man boobs. Then the moment arrived when he decided to lick my face and French kissing me. Now I’m actually trying to fight back but it’s not going well as I realize what a boob man he is. The more I push the stronger he gets and the weaker I seem to be.
Eventually it’s time for the main event as he coaxes me down by pushing my shoulders and eventually I’m on my knees and has me pull off his boxers revealing his erect, pulsating penis. He’s quite gentle now bumping it off my solidly closed lips and rubbing it all over my face, precum and all.
He very confidently looks down and mentions that it’s time as he continuously rubs it across my lips that seemingly start involuntary begin to open as he gently puts it in my mouth and says that I know exactly what to do. I reluctantly but willingly start sucking as it grows in my mouth. The motion is smooth as his penis and my tongue work in unison and he is pleased leaning back with enjoyment. We all know what comes next as him being a guy palms the back of my head to push it in my mouth the way he wanted it and to show his dominance. This goes on a while when I notice he’s full of goosebumps and tearing up with pleasure and maybe he wasn’t the only one. I find my man boobs swell, nipples really pert and I’m rock hard. I’m totally humiliated but I’m still doing it.
He eventually pulls me away reaches back in the bag and pulls out a condom. He has me open it and wants me to put it on his Dick. I don’t know about you but I had never put a rubber on another guy’s cock before. It was the worst but I did it anyways and was actually really good at it. He then laid me on my side got behind me and slid my silk panties out of the way as he slid his cock deep into my ass with the lubed condom. After some time getting it in correctly laid on his side behind me, stuffed his hand in my bra grabbing my tit for leverage and got going on the business of kind of romantically have sex with me. He was kissing my neck and really working over my boob the whole time, telling me how beautiful and wonderful I was. I gotta admit, I didn’t see that coming or ever expected to hear it from another guy. It was amazingly creepy yet somewhat comforting.
After a while he eventually came in the condom and started falling azsleep when he wanted to thank me and reached down for a damn good hand job. The night was done with the two of us together on the couch. The next morning came and I snuck out and went home to clean up. Thank god nobody saw me as I got into my car with my girls stuff on. I showered and went to bed and slept in. Later that afternoon when I was out he dropped off my washed and dried clothes, wallet, and phone. We’ve seen each other at work and around town several times since this incident and we never bring the subject up. It’s not awkward or uncomfortable, just never spoken about. The worst part was the stupid fuck reconciled with his ex. If they break up again it’s HIM that’s giving the blowjob!!!
He reaches behind the couch and hands me a bag full of clothes and asks me to try them on. I look and it’s a blonde wig, bra and panties set amazingly in my size. He’s basically begging me to put them on because it would actually make him feel better. He was so down that I felt that if this would make him better what could it hurt? So I reluctantly agreed. Bad idea.
I check myself out in the bathroom mirror fully dressed and I had to admit I actually looked good. I came out to model for him and he asked me to sit on the couch while he got me another beer. I was pretty drUnk. He came back and kinda surprised me. He had sissy husband crossdress porn on the television and it was kinda hot, causing my erection. He gave me my beer then sat next to me on the couch and commented about my erect penis through the silk panties, god they were comfortable. He then mentioned my pert nipples but instead of just commenting, he moved his hand over and started twitching them before he began feeling me up. I finally understand how women feel when suddenly a guys hand is in their bra
I’m super uncomfortable at this point as this guy who I thought was my friend is pawing me everywhere, including “accidentally” stroking my super erect rod. From this point on he is under the assumption that I’m an actual woman really attacking my swelling man boobs. Then the moment arrived when he decided to lick my face and French kissing me. Now I’m actually trying to fight back but it’s not going well as I realize what a boob man he is. The more I push the stronger he gets and the weaker I seem to be.
Eventually it’s time for the main event as he coaxes me down by pushing my shoulders and eventually I’m on my knees and has me pull off his boxers revealing his erect, pulsating penis. He’s quite gentle now bumping it off my solidly closed lips and rubbing it all over my face, precum and all.
He very confidently looks down and mentions that it’s time as he continuously rubs it across my lips that seemingly start involuntary begin to open as he gently puts it in my mouth and says that I know exactly what to do. I reluctantly but willingly start sucking as it grows in my mouth. The motion is smooth as his penis and my tongue work in unison and he is pleased leaning back with enjoyment. We all know what comes next as him being a guy palms the back of my head to push it in my mouth the way he wanted it and to show his dominance. This goes on a while when I notice he’s full of goosebumps and tearing up with pleasure and maybe he wasn’t the only one. I find my man boobs swell, nipples really pert and I’m rock hard. I’m totally humiliated but I’m still doing it.
He eventually pulls me away reaches back in the bag and pulls out a condom. He has me open it and wants me to put it on his Dick. I don’t know about you but I had never put a rubber on another guy’s cock before. It was the worst but I did it anyways and was actually really good at it. He then laid me on my side got behind me and slid my silk panties out of the way as he slid his cock deep into my ass with the lubed condom. After some time getting it in correctly laid on his side behind me, stuffed his hand in my bra grabbing my tit for leverage and got going on the business of kind of romantically have sex with me. He was kissing my neck and really working over my boob the whole time, telling me how beautiful and wonderful I was. I gotta admit, I didn’t see that coming or ever expected to hear it from another guy. It was amazingly creepy yet somewhat comforting.
After a while he eventually came in the condom and started falling azsleep when he wanted to thank me and reached down for a damn good hand job. The night was done with the two of us together on the couch. The next morning came and I snuck out and went home to clean up. Thank god nobody saw me as I got into my car with my girls stuff on. I showered and went to bed and slept in. Later that afternoon when I was out he dropped off my washed and dried clothes, wallet, and phone. We’ve seen each other at work and around town several times since this incident and we never bring the subject up. It’s not awkward or uncomfortable, just never spoken about. The worst part was the stupid fuck reconciled with his ex. If they break up again it’s HIM that’s giving the blowjob!!!
11 months ago
