Alright so I had sex with the girl of my dreams, let call her Amanda but she was also a good friend of mine so it was a little awkward.
A little bit of background on me. I am what you guys would call a natural and I have never had much of an issue getting girls but something about this just threw me off and I need to know how to fix it.
I am in college, so is she, and we used to live together in the same house (how we met). When we met she was dating this guy, Mike, and she recently (2 weeks ago) broke up with him after dating him for 3 years. I met her about 18 months ago. She is about a year older than me and is from out of state so she didn't know too many people around here (she transferred to school here) and all of my friends graduated when I moved into that house so I also didn't know too many people either. So we hung out a lot and we flirted a lot.
In the house I moved into, there was me, her, 2 other girls and 1 older awkward guy. Both of the other girls moved out a semester into us getting there (graduated) and one had a boyfriend. The other was not very attractive but the first night we all moved in we decided to drink and go out to have a roommate bonding experience. I hooked up with the single one and since then I kind of got the reputation as a partier/guy that hooks up with a lot of girls. I never hooked up with her again.
Anyways like I said the two girls moved out a semester in so me and Amanda became good friends and we would sit outside and smoke together and flirt a lot but she was dating mike and I got cheated on in my first relationship (eons ago) so I've always been against cheating. We also became friends with neighbors to the left (Dans house), our neighbors to the right (Sarahs house) and the neighbors two to the right (Kevins house). A year after living there, after my lease expired I moved out to Kevins house but me and Amanda kept in touch and hung out all the time, with the neighbors as well.
Side story but the awkward guy fell in love iwth her and would write her poems and send her long emails and shit and I tried to help him get with her but she felt really weird about it and after I moved out apparently threatened him with a restraining order and he left.
Anyways Amanda broke up with her boyfriend and like a week later was at my house hanging out and things got heated and we had sex. We wanted it to be a friends with benefits kind of thing but it was ...not great.
When we started going at it we were sitting on my couch and I kissed her and then we kinda paused and evaluated and decided on a friends with benefits kind of thing and then we just started hooking up again and she started giving me head on the couch but she was worried about my roommates coming up (even though 1 was asleep and the other was at work) so whenever there was a creek (it was middle of the night) she would stop and pretend nothing was happening real quick but then resume with it which through me off but whatever. Eventually we went up to my room and were having sex but it wasn't great. She couldn't get me off by giving me head and she really wanted to (she always claimed to be very good at giving head and she wasn't bad at it at all but wasn't the best I ever had) and she couldn't. We also randomly were laughing during it which was just fucking awkward. It was like that scene in friends where ross and rachel are about to do something (ross grabs her ass) but shes laughing and then she tells him to just stick his hands out and she'll back into it or something. Anyways pretty awkward, finally give up on her giving me head and we just start fucking and I start doing her doggy style but it keeps popping out and shes kinda small so she was too low on the bed and I was nervous (should have propped her up on a pillow in retrospect but I didn't). Anyways I eventually just finish by me basically jacking off while she plays with my balls/uses her mouth and she swallows and we just lay together for hours. Like we're randomly talking about stuff and making out. But she says something about how this was a failed experiment and never again. But we laugh about it and stay together all night and continue to make out.
She used her teeth a little bit while giving me head and I called her out on that which made me not 100% hard and she jokes about me being soft while I joke about her smile/teeth.
Around 6 AM she goes back to her place (2 doors down) and she runs into her roommate Nick (who used to live at Dans house) and he knows that she hooked up with someone. She told him it was a random guy because neither one of us want our friends to know we hooked up. (this was last thursday morning/we hooked up on a wednesday).
I went to atlantic city this past weekend (my bday was saturday) and we didn't really talk at all but she came over tonight (just left, nothing happened). Between last thursday and now, here is our text conversation between the night we had sex and prior to her coming over tonight:
April 18th (we went out to a party the night before at Dans house):
Me: Dude thats fucked up.
Her: What are you talking about?
Me: Knowing the girl Kevin brought bac was a virgin but letting him waste his time on her lol... Hilarious though!
Her: Yea I didn't know that at all. Not sure if you guys are trying to mess with me, but this isn't the best week to do that.
Her: That sounded kind of pissy - I didn't mean it that way
but I really had no clue that girl was a virgin. Me: Just messing with you haha. Busy week?
Her: Rough. Ha I need a dozen happy hours right about now.
Me: Heh, well I'd be down to go tomorrow if you are. You usually get back [from work] later though right?
--break in convo--
Me: Wanna go out tonight actually?
Her: I'd be down for drinking or hanging out at the house, but I have work tomorrow morninig so I'm not down for going out. PLUS I've had a week and a half, I'm thinking I'd be better to play it semi-cool tonight.
Me: Had a week and a half..? Alright well I'll hit you up when I'm home. Around 9:30 prob
Her: That's so late! I want to hang out at 6!
Me: I'm at work.
Her: Well you should rethink your priorities.
Me: Haha well if I could get out of it I would. Want to reschedule to tomorrow afternoon/evening?
Her: Hell no. Can't back down now.
Me: See you tonight.
-- Break in convo --
Me: Her its just kevin and I chillin right now but you can head over whenever.
--> We hung out that night, with dans house and everyone. My friends and I went to the bar but she stayed in. I didn't know at the itme but the reason she said she had a rough week was because she had JUST broken up with Mike. (Yes I thought she meant she was on her period, I know you did too)
April 25th (Morning after we had sex)
Her: You know what, I think what I was trying to say is you're really soft
Night!Me: Hahahhaha... btw don't forget to brush your teeth. Everyone at work needs to see that perfect smile
[making fun of her using teeth during her blowjob// I know that comes off as me being a fucking pushover but its not meant that way at all]Her: Don't worry, it was the first thing I did when I got home. Burn?
Me: Dunno why you had to do that.. I mean I basically had to do all the work myself so I doubt it was that necessary. Burn?
Me: (two seconds later) I know, I know, I'm "such an ass." Haha
Her: I must say that a lot.
Me: You do but to be fair I probably deserve it.
--Break in conversation--
Me: Holy shit dude have yous een FML today? Front page: "today I finally hooked up with the guy I have been in love with forever. If there is such thing as soul mates this guy is it. He's my best friend in the whole world. IT WAS THE WORST SEX I"VEEVER HAD. Fml." hahahahahhahahahah
Her: Hahah I just got out [of work]. And surprisingly I had the most epic day at work. No sleep ddi me some good.
Her: Btw Nick was home when I got home (we commuted to work together with Dan) and congratulated me. If only he knew how awkward the night was I'm pretty sure he would have taken back my high five. I told him it was a random person, don't fret.
Me: Haha good. We should leave it at that. We should go out though, I could use that bathroom stall wingman-ing thing.
Her: Gross.
Me: Whaaat? Did you forgot about our conversation about how girls in the bars talk in the bathroom [about whether to just make out with a guy or to go home with him -- she said she would pretend to be interested in me to get other girls jealous]
Her: I'm just playing. I hear you're too good for wingmen [I prefer to just talk to girls and pick them up myself, I hate when my friends see me talking to a girl and just walk up and stand there awkwardly until introduced] It's probably better though, I wouldn't want to lead girls into dissapointment ;-D
Me: Ouchhh... or maybe we should just go to old ladies homes so I can find someone without teeth!?
Her: JUST messing with you I hope you know. Don't want to cross a line, I just enjoy playful banter.
Me: Haha there's nothing you could say that would actually hurt my feelings. I'm messsing with you also as usual obviously.
Her: Okay good. I know there's a line there somewhere - there's only so much self esteem to be lost.
Me: Dunno I'm basically at zero. Can't go much lower haha.
Her: hahahah what were with thinking?
Her: Like at each step it was like this is bad, but I bet the next stage would be better. Fail.
Me: RIGHT!? It's because we're bothing fucking optimists. Fuck optimisim. Also, not gonna lie, seemed like a good idea at the time.
Her: HA, nothing good happens after 3am. I should have known.
Me: Dammit teds mom is always right. I gotta get you a link to the most recent season too that reminds me.
--break in convo--
Her; YOu know what? Fuck that. We're awesome. We don't give, even when the future looks bleak, we're champions.
Her: Thats nto his last name is it?
Her: Never again?
--break in convo-- (I was at work so I couldn't respond to these texts)
Me: What? Ted is from how I met your mother and in one episode he talks about how his mom says nothing good happens after 3am and then tells a story about how he went out after 3am.
Me: Damn fucking right we're champions! When we mess up we just get back to training and win fucking first place.
Me: Not gonna lie.. Never again is probably for the best.. But I've had fleeting thoughts of how we could make it much better. Like my bed is low and you are small so when we went doggy style I should have propped you up on a pillow or something. But yeah probably a conversation to have in person.. Or never.
Her: Yea, I know the episode, slow one, I don't think you have his last name right.
Me: I never said his last name? It's mosby but I was talking about his mom.. Myabe you misread the text?
Her: I feel like any effort we ever make would only be to restore any sense of self esteem that, let's be honest, we still have, because we're both chalking it up to being the other ones fault.
Me: Yeah... why don't we just blame the blanket and be done with it haha.
Her: I'm probably going to blame you and convince myself I'm right next time I'm in bed and it's awesome. You can do the same for me. Such a failed experiment. Our next partners are going to have no idea why were so happy when things go well.
Me: Hahhahahahha yeah. They will just think they were awesome in bed and their next partners will crush their self esteem and the vicious cycle begins anew.
Me: The thing is guys will very rarely if ever say a girl is bad in bed so you're pobably gonna get raving reviews the next time whereas I've gotta bring my A game. A lot of pressure..
Her: Please, girls never say anything. ANd I always bring my a game, it's not my fault you didn't know how to pick it up
Me: Girls don't say shit but I know when they were dissapointed .. Damn you made me so damn nervous for my next one. Btw send you a link on facebook for the new season of HIMYM
Her: Yessss!
Her: Are you serious? You could not have messed with me more. Haha so much for being prepared my next time.
Me: Dude I feel like I fucking lasted too long.. [because she couldn't get me off with just head].. I didn't know that was a thing until last night.
Me: And like every time someone laughs I'm gonna probably have a fucking 20 minute conversation or something. I can't handle these responsibilities.
Her: Hahaha so many remarks I could make, I'll be nice this time
Me: Please be brutally honest.
--break in convo--
Me: Damn are you writing a really fucking long text? Fml.
Her: hahaha no no. I was in class.
Me: How did you pull off the 'random guy' if you just walked up with just a laptop? Btw have you seen your facebook? [made a subtle joke about her smile/teeth on it]
Her: no, why?
Me: You'll see lol. Nothing to be alarmed about but I thought you might appreciate some subtle humor I posted on your wall.
Her: ...Oh I see. I'll make sure to check that out. It's on.
Her: Haha it wasn't like he was waiting for me at the door.
Me: I figured he was in the living room lol
--Break in convo--
Her: Did you get any sleep?
Me: No lol, fucking started working out/stretching because I felt terrible lol.
Her: Aw you poor baby. ANd yet you want to go out tonight?
Me: Hell yeah, gotta find osmeone to help me get my confidence up haha. Did you want to?
Me: Go out I mean.
Her: Ha, I like that you felt the need to clarify.
Me: Shush you, it's not awkward unless you make it so.
Her: Who are you trying to convince? Ha I'm jellin.
--Break in convo --
Her: Are you @ your house?
--Break in convo --
Her: Alright wheen you are you have a package here.
[I was at work, I think she was drunk because of the extra e in when and the extra 'you' instead of 'here'. I took the package thing to mean a sex thing but she actually had some of my mail that got delivered to her house]
--Break in convo --
Me: Just got off work brah. My friends are coming over at 9:30/10
Me: The package is at your place?
Me: I see no package [I thought she meant she was in front of my place and saw a package originally, but actually it was delivered to her house]
Her: At 8306 (Dan's house)
Me: That doesn't help me at all lol. Should I swing by and grab this package or should I just get it later? I am going to be in AC until Sunday evening so I can't grab it till then if not tonight .
[Basically I wanted her to leave Dan's place alone so I could fuck her again]
Her: At dans now. You could pick it up later? Or I could just drop it off tomorrow.
Me: I'll pick it up later tonight. Hit me up when you leave?
Her: Aren't you out with your friends?
Me: Drinking and watching the NFL draft at my place but depending on what time you leave I can meet up with you before we go to the bar [the bar is literally 5 minutes away walking -- and it was like 10:30pm at this time]
Her: haha that's what we're doing.
Me: Well y'all are welcome to come over here and combine parties if you want.
[she/they didn't come and I went out with friends)
--break in convo--
Me: [2 AM drunk text] Hey my friends just left but I'm leaving for AC before noon tomorrow. You mind if I grab that package now?
--break in convo--
April 26th:
Her: Serious question. What do I need to do to make sure we won't speak of this? I shouldn't not have done that so fast after a relationship and I feel awful. I don't know what I would do with myself if that information was passed along.
Me: I'm not telling anyone. I promise you that. I don't want people to know either... Don't worrry./ I know you probably don't believe me but I'm not going to break this promise to you. Why are you bring this up again? Especially over text...
Her: I woke up thinking I was a bad person... was afraif of the person I would hurt if they ever found out. [she means her ex]
Me: Amanda you are single you do not need to feel guilty for doing anything with me or anyone else. Stop second guessing yourself. There is noone that should be hurt if they fudn out what we did. Regardless, I'm not telling anyone. Btw, since youa re awake can I grab that package? Was it from amazon?
Me: Sorry for the urgency but I suspect it's something for my birthday.
Her: Dropping your package off at your house now, that alright?
Me: Yeah.
Her: You there? or should I just leave it on the steps.
Me: I'm here.
[we talked for a bit, I was in a wifebeater in the sun and these scars I have on my left shoulder from when I got stabbed were mentioned. We continued our conversation she said I looked like wolverine from xmen/pretty badass, etc.]
Her: Thanks for responding the way you did this morning regardless of how irrational you think I was being. You're a sweetheart (accept it), and I really appreciate it. Thank you.
Me: No I'm badass. Like super manly and wolverine scared and lumberjack beard and all. Badass as it gets. None of that sensitivity bullshit here. But seriously you're welcome and you know that you can talk to me whenever, even if its about me
Her: Lumberjack beard? Please. I'll give you everything else.
--break in convo--
Her: Are you leaving tonight?
Me: I'm leaving in like an hour. But you/me/whoever is around/hookah date when I get back.
Her: Deal.
--Break in convo--
Her: They say bad experiences bring friends closer. I concur.
Me: Depends on the friend.
Her: Well we're both pretty epic.
--> I leave for AC, come back Sunday.
April 28th:
Me: We still on for tonight?
Her: Actually I forgot I had a dinner date with my girlfriend in DC tonight. We're eating grasshopper tacos! - apparently its a big thing?
Me: I heard its equally good for you and doesn't taste bad or somthing... Anyways let me know how it is. Let me know if you wanna hang out sometime.
Me: Dammit I hate that I feel the need to clarify but.. I didn't mean as if you wanna do what we did the last time we chilled.. Just if you wanna hang out I mean.
Her: hahahha shut your mouth.
--break in convo--
Her: We had to get drunk to get rid of the taste of grasshopper. That about sums up the experience.
Me: haha wel want to smoke hookah/watch TV? I need a study break
--break in convo--
April 29th:
Her: What are you up to tonight?
Me: Watching prometheus. You?
Her: Ha watching cartoons with dinner. Cool kid over here.
Me: Haha come over? We can plot to take over the world.
Her: Don't wanna interrupt the show, maybe after?
Me: It ends at 10? I havent started the movie yet if you want me to wait, but yeah that works. See you soon.
--break in convo--
Her: Down to smoke or you already knees deep in the movie?
Me: I'm down to smoke.
Her: Ha you sound thrilled.
Her: Also I meant hookah, not to be misleading.
Me: OMGOMGOMOG can't wait to smoke hookah when ar eyou gettin ghere!?!?!?!?
She comes over tonight and immediate the tone is all out of whack. She's wearing a v neck white tee with a lot of clevage and leggings that show off her amazing ass, and considering the time between when she texted me asking me what I'm doing and her coming over, I know she changed. BUT I have an L shaped couch and she sat like on the other leg of the L than me... so I dunno. Anyways we talk about the sex we had and how its awesome things aren't awkward between us and she was telling me how Dans house is hitting on her after that morning since Nick realized that she was having sex again or whatever. Dunno overall a pretty normal hang out session for us but no sex.
I want to hook up with her again though. Don't know how to approach it though.
P.S. The thing is I hooked up with a girl from our other neighbor Sarah's house and she talked about it and Amanda knows I can be good in bed and similarly based on our sex experience I know that she knows what she was doing but there just wasn't chemistry there in bed. Awkward because she just got out of a relationship, or because it was me and her? Or idk. Point being that I know that she doesn't think that it I'm inexperienced but that she chalks it up to us not being compatible together.. I think that works in my favor. And tonight she said as much, (she said she could tell I knew what I was doing but it just wasn't working)
Anyways we made tentative plans for Friday and next week. Dan's house is having a happy hour thing on Wednesday she said she would stop by for but I don't think I'm going to go (I have work). When I said that, she said Friday instead.
In atlantic city there was these girls on a bachlorette party and I was dancing/talking/flirting with the whole group and I was oging to go upstairs to the hotel room with one of them but I fucking kept thinking about Amanda and I didn't. I told Amanda about this; make her jealous? Idk. I was actually just being honest with her.
My confidence is so fucking shaken. I don't know what to do.