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Dating Disasters
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Straight Male / 20
Girlfriend's Mom
I've been dating my current girlfriend for about 2 years now. We'd been friends since highschool started but only started dating about a couple of months before school ended.
Even after being together for 6 months she wouldn't let me fuck her. We do oral both ways and she's really good at giving head. I love to eat her pussy too and wish I could fuck her but she's determined to be a virgin on her wedding night. She won't let me finger her even, and there's nothing going in her butt so forget anal.
A little over a year ago I was really getting frustrated. I'm not ready to get married and she agrees that we both need to wait until after college. I was telling her that maybe we should see other people for a while just to be sure about us. (I really just wanted to get laid.) She started crying as if the world was coming to an end. I told her it was just a bad idea and went home.
I got a text from her mom the next day saying we need to talk... In private!
As you can imagine I was pretty nervous about having this talk with her mom. Her mom isn't bad looking for a woman in her 40s. She's kind of short, but thin with a nice butt and small tits. Blonde hair, kinda short cut, but nice.
Anyhow I go over there and my girlfriend Chrissy isn't home, and I sit with her mom in the kitchen. She says Chrissy was crying all night so she had to dig it out of her what was bothering her. So Chrissy said you want to see other girls. Why? I tried to use the same line that I thought we both should be sure that we were the one for each other blah blah blah. She said right. Now tell me the truth. Isn't it because Chrissy won't have sex with you? I was kind of shocked and almost said well we do oral but then thought better of it. I said well, to be honest yes. It's hard not to make love to the girl you love after all, and I'm not sure I can take three more years of this. But I do love your daughter.
She goes on about how I could lose her, or what if I catch something or knock someone up? I said I guess you're right. But I still don't know if I can last until our wedding night if we make it that far. The next thing out of her mouth floored me. Well then fuck me until then.
Now I know most of you would think that I said hell yes, let's go! But I was intimidated or just unsure of myself at that time as I had little experience with sex. I had fucked a couple of girls in my life to that point. But looking back, I wasn't much good at it.
I could hardly look at her when I said are you kidding me? You must be testing me or something. She said look, I understand a young man like you had needs. I also like you and hope you and my daughter end up married one day. I would rather have some control over what you do sexually before you start having sex with Chrissy do you don't bring anything nasty home to her, or get aids and ruin your life. Besides I'm sure I can teach you how to be a good lover for her.
I said that would be a good idea I guess and she noticed the bulge in my pants and says, no time like the present to get started and took her top and bra off. She has really nice tits. Big pink nipples that looked great on her small round tits. I sucked on them right away and she seemed to like it.
She helped me learn how to eat pussy better than I was. How to tease and get her to orgasm easily and powerfully. She taught me how to make her squirt which I fucking love. Then she taught me how to fuck for more than two minutes. It took a lot of practice. I loved practicing with her. After a couple of months I was pretty good at it all. She likes it all, oral, anal, vaginal. We even do DP with her using a dildo in her pussy while I pound her ass.
Now as I got better at oral sex, Chrissy noticed my technique changed while eating her out. She asked me how come I do it different now? I said I read up on it and other things because I thought if I did it better she might give in and give up the pussy lol. She bought it. Whew!
The thing is, I'm totally into sex with her mom. We fuck so much, it's addicting. We have had weekends away together even. I usually have a few guys weekends every year so Chrissy doesn't suspect anything. She just thinks it's a shame when her mom goes to visit her grandparents at the same time when we could have alone time. Lol
I'm not sure how this will all end. Two more years until graduation, so I'm going to enjoy this while it lasts. I keep pushing Chrissy once in a while for that sweet pussy, she still hasn't given it up. But she says more and more that maybe we can do it one day since she's sure we will be getting married. Maybe for our anniversary in January.
If course I say, are you sure babe? I know I love you and I'm sure we will end up married anyhow.
I ask myself if after I start fucking Chrissy will I have to stop fucking her mom? I guess I'll cross that bridge when I come to it. I'll be giving her mom a good pounding in about an hour from now when she stops by. Should I ask her how this will all unfold when Chrissy and I start having sex? Or should I just ride it out?
Even after being together for 6 months she wouldn't let me fuck her. We do oral both ways and she's really good at giving head. I love to eat her pussy too and wish I could fuck her but she's determined to be a virgin on her wedding night. She won't let me finger her even, and there's nothing going in her butt so forget anal.
A little over a year ago I was really getting frustrated. I'm not ready to get married and she agrees that we both need to wait until after college. I was telling her that maybe we should see other people for a while just to be sure about us. (I really just wanted to get laid.) She started crying as if the world was coming to an end. I told her it was just a bad idea and went home.
I got a text from her mom the next day saying we need to talk... In private!
As you can imagine I was pretty nervous about having this talk with her mom. Her mom isn't bad looking for a woman in her 40s. She's kind of short, but thin with a nice butt and small tits. Blonde hair, kinda short cut, but nice.
Anyhow I go over there and my girlfriend Chrissy isn't home, and I sit with her mom in the kitchen. She says Chrissy was crying all night so she had to dig it out of her what was bothering her. So Chrissy said you want to see other girls. Why? I tried to use the same line that I thought we both should be sure that we were the one for each other blah blah blah. She said right. Now tell me the truth. Isn't it because Chrissy won't have sex with you? I was kind of shocked and almost said well we do oral but then thought better of it. I said well, to be honest yes. It's hard not to make love to the girl you love after all, and I'm not sure I can take three more years of this. But I do love your daughter.
She goes on about how I could lose her, or what if I catch something or knock someone up? I said I guess you're right. But I still don't know if I can last until our wedding night if we make it that far. The next thing out of her mouth floored me. Well then fuck me until then.
Now I know most of you would think that I said hell yes, let's go! But I was intimidated or just unsure of myself at that time as I had little experience with sex. I had fucked a couple of girls in my life to that point. But looking back, I wasn't much good at it.
I could hardly look at her when I said are you kidding me? You must be testing me or something. She said look, I understand a young man like you had needs. I also like you and hope you and my daughter end up married one day. I would rather have some control over what you do sexually before you start having sex with Chrissy do you don't bring anything nasty home to her, or get aids and ruin your life. Besides I'm sure I can teach you how to be a good lover for her.
I said that would be a good idea I guess and she noticed the bulge in my pants and says, no time like the present to get started and took her top and bra off. She has really nice tits. Big pink nipples that looked great on her small round tits. I sucked on them right away and she seemed to like it.
She helped me learn how to eat pussy better than I was. How to tease and get her to orgasm easily and powerfully. She taught me how to make her squirt which I fucking love. Then she taught me how to fuck for more than two minutes. It took a lot of practice. I loved practicing with her. After a couple of months I was pretty good at it all. She likes it all, oral, anal, vaginal. We even do DP with her using a dildo in her pussy while I pound her ass.
Now as I got better at oral sex, Chrissy noticed my technique changed while eating her out. She asked me how come I do it different now? I said I read up on it and other things because I thought if I did it better she might give in and give up the pussy lol. She bought it. Whew!
The thing is, I'm totally into sex with her mom. We fuck so much, it's addicting. We have had weekends away together even. I usually have a few guys weekends every year so Chrissy doesn't suspect anything. She just thinks it's a shame when her mom goes to visit her grandparents at the same time when we could have alone time. Lol
I'm not sure how this will all end. Two more years until graduation, so I'm going to enjoy this while it lasts. I keep pushing Chrissy once in a while for that sweet pussy, she still hasn't given it up. But she says more and more that maybe we can do it one day since she's sure we will be getting married. Maybe for our anniversary in January.
If course I say, are you sure babe? I know I love you and I'm sure we will end up married anyhow.
I ask myself if after I start fucking Chrissy will I have to stop fucking her mom? I guess I'll cross that bridge when I come to it. I'll be giving her mom a good pounding in about an hour from now when she stops by. Should I ask her how this will all unfold when Chrissy and I start having sex? Or should I just ride it out?
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