- Joined
- Jul 6, 2017
- Messages
- 20
This is an outing I had about a year ago. I'm a little late posting the report 
I met this chick at a bar crawl and took her number. A couple of weeks later, I schedule a meet and go out with her. When the day comes, I text her about an hour before our date to confirm we’re still meeting up. Shes says yes but asks if we can meet an hour later than scheduled. I say okay. She was at a pool party and said she needed to go home to get ready. I picked a dive bar near my place and I get there before she does. I wait for her inside the bar and she texts me saying she’s going to be a few minutes late. When she walks in, it’s about 10 after. She’s 50 years old, I was 30 at the time, but she looks good for her age. She has long blonde hair, big boobs, she’s a little chubby but she has nice legs and her face is cute enough.
We hug and go to the bar to order drinks. We each get rum and coke, she also gets a water, and I walk us over towards the back of the bar where there’s a circular booth. We sit on opposite sides and the table moves whenever she or I put weight on it. She talks about how she’d already been drinking at the pool party she was just at and says she’s dehydrated from being in the sun all day. After talking for a while, we go to get another round. When we come back, I make it a point to sit next to her so I can be closer and start touching her. We talk some more for a while and I begin touching her leg underneath the table. After about two hours, I ask if she wants to go back to my place to watch a movie. She agrees and we leave the bar and go to her car.
She’s parked closer than I am, so she drives me to my truck. It’s dark out now and I tell her to follow me and on the way back to my pad I have a couple of close calls. I get in my truck and back out of the parking space. While I’m backing up, I’m not paying attention to my right-hand side and I almost hit a car that’s parked behind me. I have her follow me but on the way, she falls behind so I pull over to the side of the road to let her catch up. Once I see her coming, I check to see if any cars are coming and merge back onto the road and almost hit a car as it passes me. I swear I didn’t see it.
After these two close calls, I make it back home and I have her park at the church next to my place. When we get inside, she uses the bathroom while I put the tv on. She comes out of the bathroom and I offer her a drink. She asks for water and says she’s still dehydrated. I give her water and I go use the bathroom myself.. I get out and pour myself a glass of water and walk over to the couch where she is sitting and begin browsing netflix. She’s sitting on the side of the couch that’s closest to the door. I’m hoping this makes her more comfortable so she can feel like she could leave if she wanted to and not like she’s being held hostage. I pick a movie but it loads to 10% and stops. I exit that one and try another but it does the same thing. I consider putting on Youtube instead but I restart Netflix and it works fine after that.
While the movie’s playing, we talk some more about her tattoos and she shows me some more of them. We watch the movie for about 10 minutes and I say her lips look dry and she should bring them over here. She laughs but I hesitate and I don’t go for the kiss. After watching the movie for a few more minutes and procrastinating, I call her name to get her attention and begin kissing her.
We make out for a minute while I touch her leg. We stop and go back to watching the movie for a little bit then I begin kissing her again, this time touching more of her body and moving my hand up and down her leg. I also kiss her neck. I take her by the hand and lead her into the bedroom. We sit on the bed and start making out some more. Then she starts having second thoughts and stops.
“I’m so much older than you” She says.
“I’m okay with it if you are. It doesn’t bother me.”
“Really? I’m so much older than you.”
“It doesn’t bother me.”
“What are you trying to do?”
“I’m just looking to date and have some fun. I’m not trying to rush into a relationship or anything.”
“Then we shouldn’t rush into sex.”
We both stay quiet for a moment.
Me: “ What are you looking for?”
Her: “ Not to just date and have fun. You were really persistent.
Me: “ You like persistent, right?”
Her: “Yeah. You wore me down”.
We sit there for a minute and I consider saying something else but I decide not to and start kissing her again. While we’re making out, her phone rings. I worry that it’s her daughter cause she had mentioned earlier that she might have to go pick her daughter up. She ignores it and we continue making out. It rings again so we stop and she tells me she needs to check her phone cause it may be her daughter. She goes back to the living room where she left her phone. I wait in my room for her to come back but she doesn’t return right away so I go check on her. She’s texting someone. I left the tv going so I stand there watching it while I wait for her to finish.She sets her phone down and I stand there pondering what to do next. I’m not sure if I should take her to the room again or just let it go at this point. Fortunately, she asks if I want to go back to the room to which I respond yes and lead her back.
We sit on the bed and start making out again. I debate turning the lights off but I don’t wanna stop in case she changes her mind again. I lie her down on the bed and I’m on top of her now. I take off her dress and my clothes so I’m only in my underwear now. I have to say, she looked better to me with her clothes on than with her clothes off. She has kind of a big belly and she has stretch marks underneath her stomach. I make out with her again, kissing her neck and touching her all over but I’m not getting hard. I even pull one of her tits out but it still doesn’t do it for me, she has big nipples which I personally am not a fan of. I start to worry in my mind that I’m not going to get hard. I want to because I’m so close but it’s not happening. I try dry humping her but that doesn’t work. We’re still in our underwear at this point.
I really like cowgirl so I put her on top of me and she starts grinding on me. This doesn’t work either. I start undoing her bra but I can’t get the last hook so she gets it for me. She also has the same stretch marks underneath her boobs. She stops cause she says she’s getting hot and asks if I can turn on the fan so I turn the fan on but I also leave the light on. She’s starts grinding on me again but now my mind is in a full sprint running all sorts of calculations. I start worrying what my friends will think when I tell them I had a half-naked woman on top of me and I couldn’t get hard.
“Will they think I’m gay?” I wonder. “I can’t tell them. I’ll have to make something up.” I start thinking about what I’m going to tell them while she continues to grind. I’m also worrying she’s going to lose patience with me and stop. I wonder how much more time she’s going to give me until she says fuck it. My mental panicking gets so bad I even start to question my own sexuality. Another thing that bugs me is some of the loose hairs of my torso are on her stomach so I start picking them off her body like a monkey. Eventually she does stop and lies down next to me with my arm around her.
“Well that was a different kind of sex.” She says.
“Yeah.” I respond. I don’t know what else to say.
I’m lying there in disappointment now. My mind is too busy running through what just happened that I can’t think of anything to say. Aside from her noticing my motorcycle helmets, we just lie there in silence until she decides to get ready to leave. She gets dressed and I walk her out to her car. We get to her car and hug. I ask her if she’s sure she didn’t forget anything and she says yes. She gets in her car and I wish her a good night then she leaves.
I met this chick at a bar crawl and took her number. A couple of weeks later, I schedule a meet and go out with her. When the day comes, I text her about an hour before our date to confirm we’re still meeting up. Shes says yes but asks if we can meet an hour later than scheduled. I say okay. She was at a pool party and said she needed to go home to get ready. I picked a dive bar near my place and I get there before she does. I wait for her inside the bar and she texts me saying she’s going to be a few minutes late. When she walks in, it’s about 10 after. She’s 50 years old, I was 30 at the time, but she looks good for her age. She has long blonde hair, big boobs, she’s a little chubby but she has nice legs and her face is cute enough.
We hug and go to the bar to order drinks. We each get rum and coke, she also gets a water, and I walk us over towards the back of the bar where there’s a circular booth. We sit on opposite sides and the table moves whenever she or I put weight on it. She talks about how she’d already been drinking at the pool party she was just at and says she’s dehydrated from being in the sun all day. After talking for a while, we go to get another round. When we come back, I make it a point to sit next to her so I can be closer and start touching her. We talk some more for a while and I begin touching her leg underneath the table. After about two hours, I ask if she wants to go back to my place to watch a movie. She agrees and we leave the bar and go to her car.
She’s parked closer than I am, so she drives me to my truck. It’s dark out now and I tell her to follow me and on the way back to my pad I have a couple of close calls. I get in my truck and back out of the parking space. While I’m backing up, I’m not paying attention to my right-hand side and I almost hit a car that’s parked behind me. I have her follow me but on the way, she falls behind so I pull over to the side of the road to let her catch up. Once I see her coming, I check to see if any cars are coming and merge back onto the road and almost hit a car as it passes me. I swear I didn’t see it.
After these two close calls, I make it back home and I have her park at the church next to my place. When we get inside, she uses the bathroom while I put the tv on. She comes out of the bathroom and I offer her a drink. She asks for water and says she’s still dehydrated. I give her water and I go use the bathroom myself.. I get out and pour myself a glass of water and walk over to the couch where she is sitting and begin browsing netflix. She’s sitting on the side of the couch that’s closest to the door. I’m hoping this makes her more comfortable so she can feel like she could leave if she wanted to and not like she’s being held hostage. I pick a movie but it loads to 10% and stops. I exit that one and try another but it does the same thing. I consider putting on Youtube instead but I restart Netflix and it works fine after that.
While the movie’s playing, we talk some more about her tattoos and she shows me some more of them. We watch the movie for about 10 minutes and I say her lips look dry and she should bring them over here. She laughs but I hesitate and I don’t go for the kiss. After watching the movie for a few more minutes and procrastinating, I call her name to get her attention and begin kissing her.
We make out for a minute while I touch her leg. We stop and go back to watching the movie for a little bit then I begin kissing her again, this time touching more of her body and moving my hand up and down her leg. I also kiss her neck. I take her by the hand and lead her into the bedroom. We sit on the bed and start making out some more. Then she starts having second thoughts and stops.
“I’m so much older than you” She says.
“I’m okay with it if you are. It doesn’t bother me.”
“Really? I’m so much older than you.”
“It doesn’t bother me.”
“What are you trying to do?”
“I’m just looking to date and have some fun. I’m not trying to rush into a relationship or anything.”
“Then we shouldn’t rush into sex.”
We both stay quiet for a moment.
Me: “ What are you looking for?”
Her: “ Not to just date and have fun. You were really persistent.
Me: “ You like persistent, right?”
Her: “Yeah. You wore me down”.
We sit there for a minute and I consider saying something else but I decide not to and start kissing her again. While we’re making out, her phone rings. I worry that it’s her daughter cause she had mentioned earlier that she might have to go pick her daughter up. She ignores it and we continue making out. It rings again so we stop and she tells me she needs to check her phone cause it may be her daughter. She goes back to the living room where she left her phone. I wait in my room for her to come back but she doesn’t return right away so I go check on her. She’s texting someone. I left the tv going so I stand there watching it while I wait for her to finish.She sets her phone down and I stand there pondering what to do next. I’m not sure if I should take her to the room again or just let it go at this point. Fortunately, she asks if I want to go back to the room to which I respond yes and lead her back.
We sit on the bed and start making out again. I debate turning the lights off but I don’t wanna stop in case she changes her mind again. I lie her down on the bed and I’m on top of her now. I take off her dress and my clothes so I’m only in my underwear now. I have to say, she looked better to me with her clothes on than with her clothes off. She has kind of a big belly and she has stretch marks underneath her stomach. I make out with her again, kissing her neck and touching her all over but I’m not getting hard. I even pull one of her tits out but it still doesn’t do it for me, she has big nipples which I personally am not a fan of. I start to worry in my mind that I’m not going to get hard. I want to because I’m so close but it’s not happening. I try dry humping her but that doesn’t work. We’re still in our underwear at this point.
I really like cowgirl so I put her on top of me and she starts grinding on me. This doesn’t work either. I start undoing her bra but I can’t get the last hook so she gets it for me. She also has the same stretch marks underneath her boobs. She stops cause she says she’s getting hot and asks if I can turn on the fan so I turn the fan on but I also leave the light on. She’s starts grinding on me again but now my mind is in a full sprint running all sorts of calculations. I start worrying what my friends will think when I tell them I had a half-naked woman on top of me and I couldn’t get hard.
“Will they think I’m gay?” I wonder. “I can’t tell them. I’ll have to make something up.” I start thinking about what I’m going to tell them while she continues to grind. I’m also worrying she’s going to lose patience with me and stop. I wonder how much more time she’s going to give me until she says fuck it. My mental panicking gets so bad I even start to question my own sexuality. Another thing that bugs me is some of the loose hairs of my torso are on her stomach so I start picking them off her body like a monkey. Eventually she does stop and lies down next to me with my arm around her.
“Well that was a different kind of sex.” She says.
“Yeah.” I respond. I don’t know what else to say.
I’m lying there in disappointment now. My mind is too busy running through what just happened that I can’t think of anything to say. Aside from her noticing my motorcycle helmets, we just lie there in silence until she decides to get ready to leave. She gets dressed and I walk her out to her car. We get to her car and hug. I ask her if she’s sure she didn’t forget anything and she says yes. She gets in her car and I wish her a good night then she leaves.
