Weird night.
So, first day of the conference yesterday I get sat next to a fairly good looking girl. We are partners for all the dumb little activities, and we have lunch together. She's 31 and while being very serious, (I kept having to follow quips up with "I was just joking there" when met with silence, and then she would say "I know, it was funny" without laughing, lol) I was feeling fortunate. Near the end of the day, she said she was hoping to go to a theater performance that night, and I said "If you want some company, I wouldn't mind going.", and she said "Yes, thats what I was asking."
Now again, this whole time, she's been very serious, at no point did I get a flirting vibe or anything, even though I clearly was. So, after the conference, I go back to my room and brush my teeth/grab a couple condoms, because why not be prepared, just in case. Well, she calls me and says she is on her way to get me, I offer to drive, but she insists. She's very serious, I kind of wonder why I'm even going. She picks me up and drives me to this theater. When we are getting out of the car her phone starts ringing, she looks at it, and says "It's my husband, don't say anything." I go "Ohh sure." and kind of stand there dumbly. She starts talking on the phone with her husband, reaches out, takes my hand, and starts walking. So now I'm holding hands with her, walking up to the entrance of this place, as she tells her husband what she is doing and tells him she will take pictures, and wishes he was there. She makes the whole thing sound like she is alone.
When she gets off the phone, she says "Sorry about that, did holding your hand make it a little less weird?" and I say "Well, that was nice, so I suppose it did."
We sit down, and as soon as the show starts she is rubbing my back, and putting her hand on my leg, etc. I put my hand on her leg and watch the show. Midway through she slides her hand up and gives my cock a squeeze. I look over and she is smiling, first time I've seen her smile, and says "The play is that way" and points back to the stage. She moves her hand back to my leg, and we finish the play. Afterwords, we go back to her car and she asks if I want to go get some food, its just about 10pm at this point, and I say "Sure, if you want to, I'm pretty much fine.", she says she is too, but maybe we will stop somewhere for a drink. When she starts driving I lean over and put my hand on the far side of her neck, and kind of pull her in while I kiss her neck a couple of times, she kind of purrs, and I say "I'd actually just really like to go back to the hotel." and she says "That's where I was going."
Her husband calls again on the drive there, and she tells him she is going to eat and then go to bed. She talks about her kid school as well. I sit there half heartedly ask myself if any of this bothers me. I decide it bothers me less than sex excites me.
We get back to her hotel room, and she kicks off her shoes, and flops down onto the bed. I kick my shoes off too, and climb on top of her, kissing her neck, and then face, and mouth. She pretty much immediately is reaching down while I'm kissing her, and pulling my cock out from my fly. She's in a dress, and rubs my cock up against her pussy, although she still has her panties on. I start to try to pull her dress off, and she stops me and asks me to turn the light off. I tell her I would like to see her, and she says she isn't comfortable. I turn the bathroom light on, crack the door, and turn off the lights, ask her if the dim light is ok. She says yes, I fully undress and so does she. I try to go down on her but she after 5 seconds she is pulling me up to kiss me. She's grabbing my cock and trying to pull it up to her. I stop her and tell her I need to grab a condom. She says good idea and I stand up to get it. I grab one and go to open it, and she lays on her stomach and starts going down on me. I let her and just hold the condom in my hand a minute. She is ALMOST deep throating me, like, all but half an inch or something, it was pretttttty fucking awesome.
After a few minutes I pull her off and she lays on her back, I put the condom on, and we do that for a few minutes. She kind of surprises me and pushes me, springs up, and goes into doggy style. We do that a bit. After a while I'm getting tired and slowing down, and she goes "I can't tell if you are stopping or just slowing down" I told her I was just getting tired and would she ride me a bit. She was like "I'll try, I don't really know how" and she tried, but it wasn't doing much other than giving me a break. At this point it had probably been 25-30 minutes, and she asks me if shes not doing it right, or doesn't feel good or something. I tell her now, I'm just enjoying it and am not ready to be done yet. I flip her back over, and start doing missionary again, and holding her legs up over my shoulder. Maybe another 15 minutes like this, and 2 more times she is like "I'm sorry, am I too lose, tell me what you want me to do?" she was just really worried about it. I kept saying nice things, telling her how amazing she was and beautifull, how good she felt, things like that, and you could tell she was into it, but I think the timespan just made her think I was lying or something. She honestly did feel great, and I was just really enjoying it. At one point kind of early on she told me to cum for her, and I had to say "Ohh, I'm not even close, we have a lot more to do before that happens" or something, and increased my pace for a couple minutes to kind of show her
Well, I ask her to stand up next to the bed, and have her bend over at the waste, laying her upper torso on the bed, bed letting me fuck her from behind. I just went to town like that, knowing it would push me to orgasm. When I got close, I thought about pulling out and trying to whip the condom off and cum on her back, but then I kind of wanted to do it on her chest, so when I got close I pulled out and said "turn around" and pull the condom off. She stand up and turns around and goes "Huh, what?" looking me in the face. I say "I'm going to cum" and she says "Ok... um....what do you want me to do?"
It's like the unsexiest thing ever. So, I'm standing face to face with her, jacking my dick, and she is just very serious and matter of fact again. I say "I was going to cum.. like on your chest, ok?" And she goes. "Ohhh, um, yes, ok, sure." and drops to her knees. I stand there jerking off, but I'm not really super close anymore, and after 20 secs of so she starts sucking my cock again while I jerk off. That does it, and I say "I'm going to cum!" and she goes "MMMMMM CCCMMMMM" or something, still sucking my dick, so I cum. She sucks me for a little bit and then pulls my dick out and licks it a few times, and looks up and smiles again. I say "thank you" and she goes "No problem." and hops into bed.
I lay down next to her and kiss her neck a couple time, and then she goes "Was it really ok? Were you very dissapointed?" and I say "The only part of that I didn't enjoy was you doubting it the whole time" and she says "Sorry, I worry." I ask if she's ok, and she says yes. She's pretty much just quit though and I say "I could use some positive feedback here, now I'm feeling self conscious." She says "That was perfect.
She then exclaims "Ohh shit, I left my phone on silent, I see it flashing." and grabs her phone. Its her husband. She answers and starts talking. After 20 minutes I get up and go to the bathroom, I throw my underwear back on. I lay next to her and play puzzle and dragons. She doesn't get off the phone for almost an hour. I ask her if she wants me to sleep here, or was she planning on taking me back. She says she needs to get a shower and get some sleep, so if I want to stay that would be best. She goes to take a shower and I fall asleep.
She wakes me up. She asks me if I would mind sleeping on the couch in her room, she just doesn't feel comfortable with me in the bed. I groggily say no problem, and go to the couch thinking thats weird.
We get up this morning, everything seems fine, and we weren't in the same class for the convention today. At like 4 she asked me via text if I wanted to get dinner tonight and I said sure. I texted her a couple times for details but never heard back. She just sent me a text while I was typing this saying she is coming to get me now.
Already a weird fucking trip, but, on the bright side, sex? lol, what the fuck am I doing. >_<