Straight Male / 45
Life changes are always hard to deal with, especially when you get older, try to change friends, make new friends, get a different social circle, move out of lame relationships, and meet new people. I have been lucky, that on occasion, I've had an FWB to really enjoy their company, a lot of good sex, and unfortunately, a couple times not so good sex and lousy companionship. Through the last year or so, I have learned to enjoy chat rooms, discussion boards, online posting forums, and Omegle. Chat Roulette is another new one for me, having only recently gotten introduced to it. It's been fun to anonymously show off, and be online flirting with people I don't know, and on occasion get dirty with people who have no clue who they are talking to. I also love getting off to complete strangers, because it's private, and I'm not going to worry about running into someone I might live near or work with.
About three weeks ago, though, I was online chatting on Omegle with a bunch of different girls. It was fun in the text/chat room, and then I took it to a live camera room. I always make sure it's private, and I had never shown my face. I just don't want someone to come across me, screen shot me, or have my junk show up online. I'm not going there. Well, I'd gotten into a good hot chat with a girl, who initiated it, and she was all into it. It continued on, and slowly, the clothes started coming off. I almost jumped ship when she said she wanted to see "all" including my face. Considering her initiating the chat, and me having the idea that she was legal at best (but even that was touchy), I was hesitant. Just not really sure I wanted to go there, and for all I know, I'd get someone online that might end up acting like a total asshole. I had no ambition to get turned on, worked up, ready to blow my load, and then get laughed at or whatever. Yeah. Well that didn't happen. Just the opposite.
We were almost "there" when she said that she wanted to get off, but wanted to watch who was watching. And she wanted me to join her. I was so horny I couldn't help it. So I decided to go there. I knew there would be risks. I was scared. But I was tempted to try something new. I got the shock of my life, when we are almost completely undressed, and I see my sister's kid on the other end of the camera. I knew she was into risky stuff, into taking crazy dares, and I suspected she was into shit that my sister had no idea of. But yeah. I wasn't expecting to randomly come across my teenage niece in the chat room, half dressed in underwear and a bra, and me having a massive hard on, ready to squirt. Nor was I expecting her to tell me that we'd gotten this far, so why not finish the rest and have ourselves some fun? I knew I wasn't going to tell anyone what she was doing, because it would come out what I was doing. So yeah, say what you will, but we ended up crossing a line I'd never crossed before, sitting in my computer chair, watching my niece get off, and letting her watch me pop my load.
This past weekend, however, while I was online, I get a text message. I'd been texting friends, trying to make plans, and it hadn't panned out yet. My kids were with their mom, so I was looking at the evening alone, chilling, maybe watching movies, jerking it to some porn, whatever. A typical weekend if I didn't have something going on. When she texted me, she said she wasn't doing anything all weekend, and wanted to hang out. It wasn't usual, especially if my kids weren't home, but at that point, I was up for anything, just not really wanting to spend the whole weekend at home alone. My sister called, and asked if it was OK. I told her yeah. I wasn't doing anything. And she said that was fine, as her and her husband wanted to go out, and their youngest was staying with some friends. Matty brought her daughter over, said "thanks for letting her hang" and wanted to know if she could have a friend over too. I said sure. Well, Karley tried, with no luck, to get someone else to hang out. It ended up being the two of us. Not really "weird as she'd been over there since she was a kid.
When she went into the spare bedroom to take her clothes bag in there, and her laptop and other stuff she'd brought, she said she was going to change into her pjs since we were ordering pizza and I had junk food in the house. When I saw her go into her room to change, I walked down the hall, and about died. She was standing there in underwear and a bra just like I'd seen her wearing when I saw her get off, and let her watch me jerk off on cam a few weeks ago. It was awkward and weird at the same time, looking at her up close and in person like that, considering I'd never as much as seen her getting undressed even as a kid.
When she came out, I never let on that I'd seen anything. We were hanging out for awhile, chatting, waiting for the pizza to show up. Ended up stuffing ourselves on junk food, eating pizza, and she asked me for a wine cooler. I don't normally let that happen, but figuring she wouldn't say anything, we both had one, and were sitting there. And out of the blue she says to me "so it's not awkward sitting next to me, knowing what we were doing a couple of weeks ago?" I just kind of looked at her, and laughed awkwardly and said "well yeah. Truth be known, it is kind of weird. I wasn't sure why you wanted to stay over here. Figured maybe talk about it or something?" to which she smiles and says "well yeah. Kinda sorta". and I just said OK.
We were talking for about 20-25 minutes, after eating pizza and crap food, and ended up sitting on the couch and love seat. I finished my wine cooler, and I went up to get a beer. She said to me "can I have another one?" and I figure not a risk, as she wouldn't say anything, and was spending the night. I said yeah. I went in, and got her another one, me a drink, and came back. And as I was sitting down, she said to me "so did it do it for you?" I looked at her confused, and said "what?" and she said "well you know. Watching me". I just nodded and said yeah. I said "it's uncomfortable to admit it. But yeah. I mean, it did". She started asking me questions about being single, about dating, about stuff like that, and I said "I don't wanna talk about my sex life. Come on Karley. That's kinda weird" She just laughed and said "I'm "x" years old, not 12. Come on. I'm not lame Uncle Mark". So I don't know why, but I went there. We just started talking about it. So I threw it on her. "How about you? Exciting sex life? Lots of action? Great guys? Massive fucks? All that?" She laughed and said "Uh No. Not exactly. One guy. Who really sucked. I mean really sucked. The other guy didn't even quite finish. Pussied out, claimed my age was a factor. But yet didn't seem to be a factor while we were making out, and I was blowing him". I just started laughing and went "well thanks for that then". She cracked up.
And she looked at me. I stared at her, and she said "I'd go there if you wanna" and I said "go where?" and she looked right at me and said "I'm not stupid. I told you that if you were into me, well yeah, I'd go there even more than just watching on cam". My heart about stopped. I said "wait. What?" and she laughed and said "Yeah. That's what I'm talking about".
I felt my dick get hard. I looked at her and said "you're serious? That's just not possible" to which she says to me "why? You said you liked what you saw. You liked ME. You got into it" and I said "Yeah. But watching on cam isn't quite the same as crossing the line and having sex with someone". She just said "well I know. But I'm not gonna say anything. You know that" and I said I knew that. I was sure of it. And I said because we don't need to take that risk.
She got up, and walked over to me and said "What if I change your mind? If you decided to do it? Would you let me try?" I wanted to. I really did. I hesitated. She climbed over on me, straddled me, and pushed. I felt it jump. And she said "Oh my God". That was all it took. I could not physically control myself. Multiple times I kept saying "I don't want to get in trouble. I really don't want to fuck up my life" and she would look at me and say "It's not going to happen. I just am curious. I won't say nothing. Serious"
We ended up in our underwear and her in her bra within about 15 minutes of heavy petting and making out. I wanted ot desperately see her without anything on. So I looked at her and said "I want to see more. I don't want to sound lame, but God I really want to see more". She stood up, and pulled off the rest of her clothes. And Lord help me, I sat there staring at the same naked body I'd seen on cam three weeks ago.
She moved down, I was staring at that red patch of pubic hair, and her round boobs that were moving slowly as she moved towards me. I said "wait" and she looked at me. She said "I'm on BC. For real" and I said "but I'm not sure". She just nodded. And said "well, not to sound gross, but I brought condoms. I guess you know.." and I had to laugh. i said OK.
She went over to her purse. She got one. Handed it to me. And I unwrapped it. I looked at her. She nodded. I put it on, pulled it down my hard cock. I was sitting on the couch. She lowered herself gently to me, and I slid inside her. She was super wet. I put my arms around her, and I felt it slide deep inside her. I heard her gasp and she said "oh jesus" and I felt her shudder. I looked at her, and was going to kiss her, and I heard her say "oh my god I'm going to cum". I put my mouth on hers, and she went.
It took me about 3 minutes, and I said to her I wasn't going to be able to hold back. I came inside her. In the condom. I let loose. My body was shaking and trembling. I kept holding onto her, and she was looking at me. It was massive. I couldn't stop.
When I finally finished, she just looked at me and said "holy crap" and got off. I saw it. Condom was full of my juice. I pulled it off. I put it on the table. She looked at me. And looked at it. And said "I wanna do something" so I just nodded. She took my limp cock in her hand, and started touching it. It was soaked. Then Karley put it in her mouth. I grunted and groaned. She was licking it and sucking it. I just said "it's gonna take awhile" and she stopped, and said "I know" and said she wanted to do it. So she did.
We stopped at that point. And more later...
About three weeks ago, though, I was online chatting on Omegle with a bunch of different girls. It was fun in the text/chat room, and then I took it to a live camera room. I always make sure it's private, and I had never shown my face. I just don't want someone to come across me, screen shot me, or have my junk show up online. I'm not going there. Well, I'd gotten into a good hot chat with a girl, who initiated it, and she was all into it. It continued on, and slowly, the clothes started coming off. I almost jumped ship when she said she wanted to see "all" including my face. Considering her initiating the chat, and me having the idea that she was legal at best (but even that was touchy), I was hesitant. Just not really sure I wanted to go there, and for all I know, I'd get someone online that might end up acting like a total asshole. I had no ambition to get turned on, worked up, ready to blow my load, and then get laughed at or whatever. Yeah. Well that didn't happen. Just the opposite.
We were almost "there" when she said that she wanted to get off, but wanted to watch who was watching. And she wanted me to join her. I was so horny I couldn't help it. So I decided to go there. I knew there would be risks. I was scared. But I was tempted to try something new. I got the shock of my life, when we are almost completely undressed, and I see my sister's kid on the other end of the camera. I knew she was into risky stuff, into taking crazy dares, and I suspected she was into shit that my sister had no idea of. But yeah. I wasn't expecting to randomly come across my teenage niece in the chat room, half dressed in underwear and a bra, and me having a massive hard on, ready to squirt. Nor was I expecting her to tell me that we'd gotten this far, so why not finish the rest and have ourselves some fun? I knew I wasn't going to tell anyone what she was doing, because it would come out what I was doing. So yeah, say what you will, but we ended up crossing a line I'd never crossed before, sitting in my computer chair, watching my niece get off, and letting her watch me pop my load.
This past weekend, however, while I was online, I get a text message. I'd been texting friends, trying to make plans, and it hadn't panned out yet. My kids were with their mom, so I was looking at the evening alone, chilling, maybe watching movies, jerking it to some porn, whatever. A typical weekend if I didn't have something going on. When she texted me, she said she wasn't doing anything all weekend, and wanted to hang out. It wasn't usual, especially if my kids weren't home, but at that point, I was up for anything, just not really wanting to spend the whole weekend at home alone. My sister called, and asked if it was OK. I told her yeah. I wasn't doing anything. And she said that was fine, as her and her husband wanted to go out, and their youngest was staying with some friends. Matty brought her daughter over, said "thanks for letting her hang" and wanted to know if she could have a friend over too. I said sure. Well, Karley tried, with no luck, to get someone else to hang out. It ended up being the two of us. Not really "weird as she'd been over there since she was a kid.
When she went into the spare bedroom to take her clothes bag in there, and her laptop and other stuff she'd brought, she said she was going to change into her pjs since we were ordering pizza and I had junk food in the house. When I saw her go into her room to change, I walked down the hall, and about died. She was standing there in underwear and a bra just like I'd seen her wearing when I saw her get off, and let her watch me jerk off on cam a few weeks ago. It was awkward and weird at the same time, looking at her up close and in person like that, considering I'd never as much as seen her getting undressed even as a kid.
When she came out, I never let on that I'd seen anything. We were hanging out for awhile, chatting, waiting for the pizza to show up. Ended up stuffing ourselves on junk food, eating pizza, and she asked me for a wine cooler. I don't normally let that happen, but figuring she wouldn't say anything, we both had one, and were sitting there. And out of the blue she says to me "so it's not awkward sitting next to me, knowing what we were doing a couple of weeks ago?" I just kind of looked at her, and laughed awkwardly and said "well yeah. Truth be known, it is kind of weird. I wasn't sure why you wanted to stay over here. Figured maybe talk about it or something?" to which she smiles and says "well yeah. Kinda sorta". and I just said OK.
We were talking for about 20-25 minutes, after eating pizza and crap food, and ended up sitting on the couch and love seat. I finished my wine cooler, and I went up to get a beer. She said to me "can I have another one?" and I figure not a risk, as she wouldn't say anything, and was spending the night. I said yeah. I went in, and got her another one, me a drink, and came back. And as I was sitting down, she said to me "so did it do it for you?" I looked at her confused, and said "what?" and she said "well you know. Watching me". I just nodded and said yeah. I said "it's uncomfortable to admit it. But yeah. I mean, it did". She started asking me questions about being single, about dating, about stuff like that, and I said "I don't wanna talk about my sex life. Come on Karley. That's kinda weird" She just laughed and said "I'm "x" years old, not 12. Come on. I'm not lame Uncle Mark". So I don't know why, but I went there. We just started talking about it. So I threw it on her. "How about you? Exciting sex life? Lots of action? Great guys? Massive fucks? All that?" She laughed and said "Uh No. Not exactly. One guy. Who really sucked. I mean really sucked. The other guy didn't even quite finish. Pussied out, claimed my age was a factor. But yet didn't seem to be a factor while we were making out, and I was blowing him". I just started laughing and went "well thanks for that then". She cracked up.
And she looked at me. I stared at her, and she said "I'd go there if you wanna" and I said "go where?" and she looked right at me and said "I'm not stupid. I told you that if you were into me, well yeah, I'd go there even more than just watching on cam". My heart about stopped. I said "wait. What?" and she laughed and said "Yeah. That's what I'm talking about".
I felt my dick get hard. I looked at her and said "you're serious? That's just not possible" to which she says to me "why? You said you liked what you saw. You liked ME. You got into it" and I said "Yeah. But watching on cam isn't quite the same as crossing the line and having sex with someone". She just said "well I know. But I'm not gonna say anything. You know that" and I said I knew that. I was sure of it. And I said because we don't need to take that risk.
She got up, and walked over to me and said "What if I change your mind? If you decided to do it? Would you let me try?" I wanted to. I really did. I hesitated. She climbed over on me, straddled me, and pushed. I felt it jump. And she said "Oh my God". That was all it took. I could not physically control myself. Multiple times I kept saying "I don't want to get in trouble. I really don't want to fuck up my life" and she would look at me and say "It's not going to happen. I just am curious. I won't say nothing. Serious"
We ended up in our underwear and her in her bra within about 15 minutes of heavy petting and making out. I wanted ot desperately see her without anything on. So I looked at her and said "I want to see more. I don't want to sound lame, but God I really want to see more". She stood up, and pulled off the rest of her clothes. And Lord help me, I sat there staring at the same naked body I'd seen on cam three weeks ago.
She moved down, I was staring at that red patch of pubic hair, and her round boobs that were moving slowly as she moved towards me. I said "wait" and she looked at me. She said "I'm on BC. For real" and I said "but I'm not sure". She just nodded. And said "well, not to sound gross, but I brought condoms. I guess you know.." and I had to laugh. i said OK.
She went over to her purse. She got one. Handed it to me. And I unwrapped it. I looked at her. She nodded. I put it on, pulled it down my hard cock. I was sitting on the couch. She lowered herself gently to me, and I slid inside her. She was super wet. I put my arms around her, and I felt it slide deep inside her. I heard her gasp and she said "oh jesus" and I felt her shudder. I looked at her, and was going to kiss her, and I heard her say "oh my god I'm going to cum". I put my mouth on hers, and she went.
It took me about 3 minutes, and I said to her I wasn't going to be able to hold back. I came inside her. In the condom. I let loose. My body was shaking and trembling. I kept holding onto her, and she was looking at me. It was massive. I couldn't stop.
When I finally finished, she just looked at me and said "holy crap" and got off. I saw it. Condom was full of my juice. I pulled it off. I put it on the table. She looked at me. And looked at it. And said "I wanna do something" so I just nodded. She took my limp cock in her hand, and started touching it. It was soaked. Then Karley put it in her mouth. I grunted and groaned. She was licking it and sucking it. I just said "it's gonna take awhile" and she stopped, and said "I know" and said she wanted to do it. So she did.
We stopped at that point. And more later...
