The Wager Turned Another Out Gay
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Team Work Turned Another One Gay free porn video
Recently, I moved in with Jason, a friend from college. He and I weren't all that close even though we had plenty in common. Our lives just went in separate directions, but we both needed a place to stay around the same time. We figured we'd put our money together and find a place that accommodated both our needs. We checked out a few apartments before finding one that was a reasonable distance to both our jobs and wasn't too expensive. Between the two of us, it actually saved us money.
Isabella was Jason's best friend. I met her when she helped Jason move in. She was practically the physical representation of everything I wanted in a girlfriend. Pretty face, long dark hair, nice sized boobs that weren't ridiculously massive, and an ass that would require multiple hand prints to cover just one cheek. In other words, she's was the definition of "slim thick." The best part was that she had a great personality. We got along really well and even shared the same taste in music and movies. I didn't try asking her out when we first met as I was still on the tail end of healing from my last relationship and I was sure someone like Isabella would definitely have a boyfriend.
After settling in, Isabella started to hang out with Jason and I on the weekends on a regular basis. We'd drink, play cards, watch movies, and relax after stressful weeks at work. All in all, I was just happy to be able to live in an environment that didn't have constant conflicts like my last roommates.
A couple of months later, I got over my ex and became more and more interested in Isabella as I got to know her. I learned that she was actually single a week or two after meeting her, but at that point, I hadn't shown interest in her. I decided that I would take a chance whenever Jason stepped away so it wouldn't be too awkward.
Jason was the heaviest drinker out of the three of us and took frequent bathroom breaks. I knew it was only a matter of time that I would have an opportunity to ask Isabella out. I was anxious all week as I tried to figure out how to do it. I decided to not try to make a big deal out of it and just invite her to spend some time together during the week.
That Friday night, we all had a couple of drinks after work. We were on the couches and talking about the stupid things that happened that day. It wasn't long before Jason's runs for the bathroom started.
"So, hey," I said. "We've been hanging out pretty regularly and seemed to have a lot in common. Would you like to get to know each other a little more?"
Isabella smiled as if she knew the question was coming. She put her drink down on the table and paused for a moment. I was relieved that it seemed she was giving it some thought.
"Well, you are cute," she said, "and I have noticed you checking me out when you think I'm not looking. I'm not going to say I haven't thought about it, but right now, I'm looking for a specific type."
"And what would that I be," I asked.
"It's. . ."
She bit her lip as if she wanted to tell me, but couldn't bring herself to say it. Her face became pretty red as she blushed for embarrassment.
We heard Jason flush the toilet and she jumped. She gave me a look, and I didn't know what it meant at the time, but she suggested I give her a week to think about it. It struck me as odd, but I didn't want to come off as desperate. I casually agreed and we continued the rest of the night as normal.
The next day, I came home from running errands to find Jason practically waiting for me.
"About time you asked her out."
I sighed. For some reason I didn't think she would tell him, but I should have known.
"Yeah, but she said to give her a week to think about it," I replied.
"You poor soul," Jason remarked.
"Well I don't see you asking her out."
He chuckled at the very idea of it, but his laugh was too genuine to be snark.
"What's so funny," I asked.
"That you've known me for almost three years and never figured out that I'm gay."
I was speechless. There was nothing to indicate that Jason was gay. I started to think about any conversation we could have had that even suggested it. However, I couldn't even think of any examples of him talking about women. The closest were of him encouraging me to go talk to women he knew I was attracted to.
"I had no idea," I finally said.
"You'd be surprised how many gay guys you've probably met. Not all of us are feminine and besides our sexuality, we're just normal guys."
"Apparently," I muttered.
"Anyway, she's probably going to turn you down."
"Wait, why," I asked.
"Because she's really into bisexual guys."
"Oh."
Jason smirked at me.
"'Oh' as in you're cutting your losses," he asked, "Or that you're willing to give it a try?"
That question shocked me more than finding out about Isabella's "type." Over the years, I did get curious about trans women after I stumbled upon it in porn. Some of my favorite pornstars would occasionally work with trans women and something about it turned me on a lot. Eventually, I started watching trans porn when I was really horny and couldn't find anything good through straight porn. I never told anyone about it, but I did fantasize about it from time to time.
"I'm not hearing a no," Jason said with a devilish grin.
"I was just surprised," I said. "I haven't met anyone into something like that. I mean, most guys talk about bisexual women, but I never considered women would be into bisexual men."
"It's more common than you think. If you want, I can help you."
"How," I chucked. "I'm not into guys. I'll just move on."
"She does really like you."
"Very funny," I said as I walked into my room.
I shut the door behind me. It was a heavy blow. I didn't realize how much I had taken a liking to Isabella before that moment. I sank into my bed and stared at the ceiling. I would have to just move on because there was just no way I'd be up for it. Right?
I started to wonder if I was was even willing to give it a try. I wasn't into men at all, but I did find some trans women incredibly attractive. After a certain point, I didn't even care they had dicks anymore. I even started to like them because of it.
A thought occurred to me. I was getting this information from Jason. Sure, he's known her a long time, but how would I know if he was telling the truth? For all I know, he could have had a crush on me and was just using this opportunity to his advantage. Though, Jason didn't come off like that kind of guy. He's been a good friend and I couldn't think of anything manipulative that he's ever done.
I was lost in confusion about the whole thing when there was a knock at my door.
"I'm not buying it," I shouted.
"Will you just look at this," Jason asked.
I got up and opened the door. He handed me his phone. It was open to texts he had with Isabella. The first message I read did prove that Jason was telling the truth.
Isabella: I think he's a great guy and I really like him, but I just don't think I'd be fulfilled. I've been wanting to have a bi bf for so long and I don't want to force him to do anything just to date me. What if it offends him?
Jason: He's never said anything homophobic that I know of. I've seen him almost fight a guy for being an asshole to this gay guy in college. He doesn't give any gay vibes, but it never hurts to ask. Worst case scenario, he says no.
Isabella: Or he gets super uncomfortable when I'm around.
I handed Jason his phone and sat down on the edge of my bed. I wondered what to do next. I couldn't figure out what I wanted. On one hand, I could date someone I got along with very well and live out a fantasy I've secretly had for years. On the other hand, there were so many things that could go wrong. I started to be concerned what would happen if she and I broke up. Would she expose me out of spite?
"Wait," I said. "When did you have that conversation?"
"About a month ago. I had to go through my phone a bit to find it."
"She's been thinking about it for that long," I asked.
"She was thinking about it since the day you met. Why do you think she's been over here so much?"
"To hang out with her best friend," I said.
"To get to know you," he replied. "She was hoping that since you moved in with me, you have messed around with guys before."
He walked over to me and showed me one more message.
Isabella: I would do practically anything he wanted to do to me if he was into cocks.
I noticed the date of that message. It was the night before, not long after she left our apartment.
I took a deep breath and asked, "How would you be able to help me?"
"Simple," he said. "Since I'm assuming it would be your first time-"
I nodded.
"- then I will make it easy for you. All you have to do, is let me suck your dick."
"Okay? Say I did, that. Then what?"
"Then," he said as he walked slowly in front of me. He got on his knees and reached for my belt. "I send her a text, telling her what happened, and that you're interested. The rest will be up to you two to discuss. Deal?"
"I don't know if-"
"I do give really good blowjobs," he said. "You get to cum and get the girl you've been wanting for weeks. It's a win/win/win."
"Wait, why the third win," I asked as I started to realize I was actually getting turned on.
Jason pulled my dick out, moaned in approval of my size, then licked from the base up to the head of my cock and said, "Because I fucking love sucking cock."
I don't know if it was purely from Jason's skills or the fact that it was a new experience for me to get a blowjob from a guy, but it was a lot better than I imagined. The way he swallowed my cock while running his tongue across the shaft with every stroke. It was like he was making out with my dick and it was the best blowjob I had at the time.
I found myself getting more into it. Jason took my dick as deep in his throat as he could and rolled his eyes in pleasure. I grabbed his hair and started to thrust into his mouth as he went down on it.
"You're really fucking good at this," I said, realizing I was out of breath.
He took my cock out of his mouth for the first time and replied, "I told you, I love sucking cock."
He sucked it harder this time around. I started to pay attention to his lips and how they puffed up as he sucked my cock. The more I looked at him and how much he was enjoying himself, the more I wondered if I would be like that if I sucked cock.
I started to think about how many guys Jason has probably blown to get this good. I loved getting blowjobs, but I never actually thought about how I would give one. All the years of me fantasizing about a trans woman with a nice fat cock and I never thought about how I'd suck it.
In the heat of the moment, I allowed myself to just let go. The world was gone and all that was left was my fantasies of cocks while Jason swallowed me whole. I thought about how it would be hot to lick a cock before sucking on the head. How degrading, yet sexy, it would be to have that cock slap my face every so often between devouring it. What sent me over the edge was the thought of how this whole situation started - Isabella. I wasn't just doing this for me, I was doing it for her too. I felt myself reach the peak of an orgasm as I thought about Isabella playing with herself as she watched me suck cock.
I moaned and became more light headed with every breath. Before I knew it, my body was quivering as I unloaded in his mouth. He swallowed it all. I was staring at the ceiling, but my mind was completely elsewhere. I was sure I just heard Jason say he'll go tell Isabella.
He left my room and I didn't move. I was still out of breath from what just happened. I always thought if I hooked up with a guy, that I would cum and feel guilty about it. Instead, I was relieved. I had been denying part of my sexuality and now that it has finally happened, I knew that I needed to just embrace it. I will always love women more, but I could definitely see myself having fun with cock every so often.
As I started to become aware of my surroundings again, the clock was showing that I was daydreaming for almost an hour. I heard the doorbell ring and heard Jason open it, then nothing. I would have thought Jason would be talking to our guest, but there was no words exchanged. Instead, a shadow appeared beneath the crack of my door.
There was a knock. I realized I never put my pants back on. I damn near fell as I quickly tried to stand and pull them up in a hurry. As I stumbled, I used the doorknob to catch my balance. I opened the door to find Isabella standing in front of me.
"Did you really let Jason-suck your cock"
"Yeah," I said with a smile of relief. I knew I could tell her about everything that led up to hooking up with Jason. I knew she'd understand and not judge me for it.
"Then I don't need a week," she said. "Jason did you get it all on video" WTF video? Yeah as Jason turn on the Tv there he was sucking my cock. Jason started rubbing his cock, Well if you don't want Jason to email it to all your friends you'll suck his cock. As Jason dropped his pants stroking his semi hard cock. But what about us? I never date a guy that suck cock!
Isabella was Jason's best friend. I met her when she helped Jason move in. She was practically the physical representation of everything I wanted in a girlfriend. Pretty face, long dark hair, nice sized boobs that weren't ridiculously massive, and an ass that would require multiple hand prints to cover just one cheek. In other words, she's was the definition of "slim thick." The best part was that she had a great personality. We got along really well and even shared the same taste in music and movies. I didn't try asking her out when we first met as I was still on the tail end of healing from my last relationship and I was sure someone like Isabella would definitely have a boyfriend.
After settling in, Isabella started to hang out with Jason and I on the weekends on a regular basis. We'd drink, play cards, watch movies, and relax after stressful weeks at work. All in all, I was just happy to be able to live in an environment that didn't have constant conflicts like my last roommates.
A couple of months later, I got over my ex and became more and more interested in Isabella as I got to know her. I learned that she was actually single a week or two after meeting her, but at that point, I hadn't shown interest in her. I decided that I would take a chance whenever Jason stepped away so it wouldn't be too awkward.
Jason was the heaviest drinker out of the three of us and took frequent bathroom breaks. I knew it was only a matter of time that I would have an opportunity to ask Isabella out. I was anxious all week as I tried to figure out how to do it. I decided to not try to make a big deal out of it and just invite her to spend some time together during the week.
That Friday night, we all had a couple of drinks after work. We were on the couches and talking about the stupid things that happened that day. It wasn't long before Jason's runs for the bathroom started.
"So, hey," I said. "We've been hanging out pretty regularly and seemed to have a lot in common. Would you like to get to know each other a little more?"
Isabella smiled as if she knew the question was coming. She put her drink down on the table and paused for a moment. I was relieved that it seemed she was giving it some thought.
"Well, you are cute," she said, "and I have noticed you checking me out when you think I'm not looking. I'm not going to say I haven't thought about it, but right now, I'm looking for a specific type."
"And what would that I be," I asked.
"It's. . ."
She bit her lip as if she wanted to tell me, but couldn't bring herself to say it. Her face became pretty red as she blushed for embarrassment.
We heard Jason flush the toilet and she jumped. She gave me a look, and I didn't know what it meant at the time, but she suggested I give her a week to think about it. It struck me as odd, but I didn't want to come off as desperate. I casually agreed and we continued the rest of the night as normal.
The next day, I came home from running errands to find Jason practically waiting for me.
"About time you asked her out."
I sighed. For some reason I didn't think she would tell him, but I should have known.
"Yeah, but she said to give her a week to think about it," I replied.
"You poor soul," Jason remarked.
"Well I don't see you asking her out."
He chuckled at the very idea of it, but his laugh was too genuine to be snark.
"What's so funny," I asked.
"That you've known me for almost three years and never figured out that I'm gay."
I was speechless. There was nothing to indicate that Jason was gay. I started to think about any conversation we could have had that even suggested it. However, I couldn't even think of any examples of him talking about women. The closest were of him encouraging me to go talk to women he knew I was attracted to.
"I had no idea," I finally said.
"You'd be surprised how many gay guys you've probably met. Not all of us are feminine and besides our sexuality, we're just normal guys."
"Apparently," I muttered.
"Anyway, she's probably going to turn you down."
"Wait, why," I asked.
"Because she's really into bisexual guys."
"Oh."
Jason smirked at me.
"'Oh' as in you're cutting your losses," he asked, "Or that you're willing to give it a try?"
That question shocked me more than finding out about Isabella's "type." Over the years, I did get curious about trans women after I stumbled upon it in porn. Some of my favorite pornstars would occasionally work with trans women and something about it turned me on a lot. Eventually, I started watching trans porn when I was really horny and couldn't find anything good through straight porn. I never told anyone about it, but I did fantasize about it from time to time.
"I'm not hearing a no," Jason said with a devilish grin.
"I was just surprised," I said. "I haven't met anyone into something like that. I mean, most guys talk about bisexual women, but I never considered women would be into bisexual men."
"It's more common than you think. If you want, I can help you."
"How," I chucked. "I'm not into guys. I'll just move on."
"She does really like you."
"Very funny," I said as I walked into my room.
I shut the door behind me. It was a heavy blow. I didn't realize how much I had taken a liking to Isabella before that moment. I sank into my bed and stared at the ceiling. I would have to just move on because there was just no way I'd be up for it. Right?
I started to wonder if I was was even willing to give it a try. I wasn't into men at all, but I did find some trans women incredibly attractive. After a certain point, I didn't even care they had dicks anymore. I even started to like them because of it.
A thought occurred to me. I was getting this information from Jason. Sure, he's known her a long time, but how would I know if he was telling the truth? For all I know, he could have had a crush on me and was just using this opportunity to his advantage. Though, Jason didn't come off like that kind of guy. He's been a good friend and I couldn't think of anything manipulative that he's ever done.
I was lost in confusion about the whole thing when there was a knock at my door.
"I'm not buying it," I shouted.
"Will you just look at this," Jason asked.
I got up and opened the door. He handed me his phone. It was open to texts he had with Isabella. The first message I read did prove that Jason was telling the truth.
Isabella: I think he's a great guy and I really like him, but I just don't think I'd be fulfilled. I've been wanting to have a bi bf for so long and I don't want to force him to do anything just to date me. What if it offends him?
Jason: He's never said anything homophobic that I know of. I've seen him almost fight a guy for being an asshole to this gay guy in college. He doesn't give any gay vibes, but it never hurts to ask. Worst case scenario, he says no.
Isabella: Or he gets super uncomfortable when I'm around.
I handed Jason his phone and sat down on the edge of my bed. I wondered what to do next. I couldn't figure out what I wanted. On one hand, I could date someone I got along with very well and live out a fantasy I've secretly had for years. On the other hand, there were so many things that could go wrong. I started to be concerned what would happen if she and I broke up. Would she expose me out of spite?
"Wait," I said. "When did you have that conversation?"
"About a month ago. I had to go through my phone a bit to find it."
"She's been thinking about it for that long," I asked.
"She was thinking about it since the day you met. Why do you think she's been over here so much?"
"To hang out with her best friend," I said.
"To get to know you," he replied. "She was hoping that since you moved in with me, you have messed around with guys before."
He walked over to me and showed me one more message.
Isabella: I would do practically anything he wanted to do to me if he was into cocks.
I noticed the date of that message. It was the night before, not long after she left our apartment.
I took a deep breath and asked, "How would you be able to help me?"
"Simple," he said. "Since I'm assuming it would be your first time-"
I nodded.
"- then I will make it easy for you. All you have to do, is let me suck your dick."
"Okay? Say I did, that. Then what?"
"Then," he said as he walked slowly in front of me. He got on his knees and reached for my belt. "I send her a text, telling her what happened, and that you're interested. The rest will be up to you two to discuss. Deal?"
"I don't know if-"
"I do give really good blowjobs," he said. "You get to cum and get the girl you've been wanting for weeks. It's a win/win/win."
"Wait, why the third win," I asked as I started to realize I was actually getting turned on.
Jason pulled my dick out, moaned in approval of my size, then licked from the base up to the head of my cock and said, "Because I fucking love sucking cock."
I don't know if it was purely from Jason's skills or the fact that it was a new experience for me to get a blowjob from a guy, but it was a lot better than I imagined. The way he swallowed my cock while running his tongue across the shaft with every stroke. It was like he was making out with my dick and it was the best blowjob I had at the time.
I found myself getting more into it. Jason took my dick as deep in his throat as he could and rolled his eyes in pleasure. I grabbed his hair and started to thrust into his mouth as he went down on it.
"You're really fucking good at this," I said, realizing I was out of breath.
He took my cock out of his mouth for the first time and replied, "I told you, I love sucking cock."
He sucked it harder this time around. I started to pay attention to his lips and how they puffed up as he sucked my cock. The more I looked at him and how much he was enjoying himself, the more I wondered if I would be like that if I sucked cock.
I started to think about how many guys Jason has probably blown to get this good. I loved getting blowjobs, but I never actually thought about how I would give one. All the years of me fantasizing about a trans woman with a nice fat cock and I never thought about how I'd suck it.
In the heat of the moment, I allowed myself to just let go. The world was gone and all that was left was my fantasies of cocks while Jason swallowed me whole. I thought about how it would be hot to lick a cock before sucking on the head. How degrading, yet sexy, it would be to have that cock slap my face every so often between devouring it. What sent me over the edge was the thought of how this whole situation started - Isabella. I wasn't just doing this for me, I was doing it for her too. I felt myself reach the peak of an orgasm as I thought about Isabella playing with herself as she watched me suck cock.
I moaned and became more light headed with every breath. Before I knew it, my body was quivering as I unloaded in his mouth. He swallowed it all. I was staring at the ceiling, but my mind was completely elsewhere. I was sure I just heard Jason say he'll go tell Isabella.
He left my room and I didn't move. I was still out of breath from what just happened. I always thought if I hooked up with a guy, that I would cum and feel guilty about it. Instead, I was relieved. I had been denying part of my sexuality and now that it has finally happened, I knew that I needed to just embrace it. I will always love women more, but I could definitely see myself having fun with cock every so often.
As I started to become aware of my surroundings again, the clock was showing that I was daydreaming for almost an hour. I heard the doorbell ring and heard Jason open it, then nothing. I would have thought Jason would be talking to our guest, but there was no words exchanged. Instead, a shadow appeared beneath the crack of my door.
There was a knock. I realized I never put my pants back on. I damn near fell as I quickly tried to stand and pull them up in a hurry. As I stumbled, I used the doorknob to catch my balance. I opened the door to find Isabella standing in front of me.
"Did you really let Jason-suck your cock"
"Yeah," I said with a smile of relief. I knew I could tell her about everything that led up to hooking up with Jason. I knew she'd understand and not judge me for it.
"Then I don't need a week," she said. "Jason did you get it all on video" WTF video? Yeah as Jason turn on the Tv there he was sucking my cock. Jason started rubbing his cock, Well if you don't want Jason to email it to all your friends you'll suck his cock. As Jason dropped his pants stroking his semi hard cock. But what about us? I never date a guy that suck cock!
Cayleigh
- 22.04.2022
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