This is a continuation of my first time experimenting with a woman. You may want to check out [part 1](https://www.reddit.com/r/gonewildstories/comments/ei4665/ff_my_first_time_with_a_woman_my_roommate/) and [part 2](https://www.reddit.com/r/gonewildstories/comments/eiccu8/ff_my_first_time_with_a_woman_my_roommate_part_2/) first.
After Mary fucked me with a strap on and had a very strong orgasm from the vibrator within the strap we took a nap together in her bed. I woke up and saw Mary looking at me. I asked how long she had been looking at me and she said only a few minutes but she liked watching me sleep that I looked so peaceful. We were laying in bed facing each other naked and we started just talking. I asked her when the last time she fucked a guy. She said it had been years but confessed to fantasizing about fucking my boyfriend Tim.
She started asking me what it was like to be fucked by Tim and how he compared to other guys I had been with. I told her that he was the only guy I’d actually ever been with and I loved having sex with him, but I didn’t have any experience with other men other than being being fingered and gone down on a few times by a guy in 11th grade. And right before I met Tim I hooked up with a different guy from school and he went down on me twice. Other than that all of my other sexual experiences were either with Tim or Mary. She was a bit shocked by that I think considering how sexual I am.
I told her Tim’s cock is really thick and the first time we had sex it hurt a lot and if we don’t do it for a while it hurts and he has to loosen me up a bit. She asked how he loosens me up. I told her I have a dildo that’s about 2/3rds of his girth and he’ll use that on me to get me ready. She asked if I ever use it on myself. I told her not really that when I masturbate I prefer all clitoral play. She giggled and told me that I had the strongest orgasm she had ever seen by clit sucking. She thinks it was so strong for me because my clit is bigger than average. We started talking more about how Tim fucks me and what I like about it. One thing I told her I love is when he cums inside me. There is no better feeling. She told me even though she’s been fucked by a few different guys she’s never done that and always used condoms. I told her that Tim and I hadn’t used condoms in over 4 years which is when I started the pill. I also told her that one thing I really like that Tim does is when he’s really turned on and fucking me that he tells me how it feels which is such a huge turn on for me. I told her I also think it’s hot when I turn him on so much he can’t last and cums too fast. It doesn’t happen all the time but I like when I drive him crazy.
I asked her what she liked when she was being fucked by a guy. She said she likes the strength and while she’s not super attracted to men she loves the feeling of someone strong taking control and fucking the shit out of her. She told me that she fucked our coworker Jonathan a few times. I almost died laughing because I thought she was kidding because he’s a super nice guy, but he’s kind of a weird geek. He’s in his 30’s but acts and dresses like a 15 year old boy. She told me he has a huge cock. We both were laughing because that is all I was going to think about when I saw him at work. We started talking more and more about sex then Mary asked me about my first ever sexual experience or when I first got really horny.
When I was 14 and in 8th grade my best friend was a girl named Victoria who had an older brother Eddie who super cute and a senior in HS. I used to sleep over her house quite a bit. I woke up in the middle of the night because I had to pee. Victoria and her brother shared a bathroom that each of their rooms had a door too. I went into the bathroom and saw that Eddie’s door to his room was open a bit. I was going to close it so I could pee. When I got closer to the door I saw him on his desk chair looking at something (probably a magazine) and he was jerking off. I had never seen a real life cock in person. I had seen one porn and a few pictures thanks to my neighbor Robyn (I’ll tell that story another time). I was frozen watching him stroke it. He kept saying oh yeah Samantha take my big dick. I wasn’t sure who Samantha was but I was turned on. I felt my panties getting wet. I kind of wished I was Samantha and he was putting his dick in me. I had sexual thoughts before but not blatant like that. He started stroking it super fast and I saw him look over at the door and right into my eyes. I don’t know if he actually saw me or not because his eyes were glazed over and then he tilted his head back and cum shot out of his cock. I quickly went back to Victoria’s room and pretended to be asleep on the couch in her bedroom. After about 30 minutes of him not coming in to scold me or call me out I thought I was safe. My pussy was still throbbing. I looked over and Victoria was sound asleep. I started to rub my clit. I bit down on the pillow so no one would hear me and came so hard. I had made myself cum before but it was never that intense. I drifted right to sleep. I woke up in the morning and went to pee and was disappointed that Eddie’s door to his room was closed.
Mary had asked if I ever hooked up with him, I said no, but I told her he randomly added me to Myspace (remember Myspace?!) a few weeks ago and sent me a message with a winky face. I have no idea if he saw me that day or not we never spoke about it. Victoria and I had a falling out towards the end of 8th grade so I never really had a reason to see him anymore. I asked Mary about her first sexual experiences and when she realized she was attracted to women.
Mary told me her story involved an older brother also, but her older brother. Mary’s older brother who was 21 when she was 14 was home from college for thanksgiving and brought his new girlfriend Michelle home with him. Mary’s parents were super conservative and wouldn’t let Michelle stay in her brother’s room although it was pretty clear they were sleeping together in college. Mary was instructed to share her room with Michelle for the weekend. Mary grew up pretty well off and had her own room that included her own bathroom. Mary had come into her bedroom and without thinking just walked in and there was Michelle sitting topless at Mary’s desk doing her makeup. Michelle smiled and said oh hi come in. Sorry I always make a mess of my clothes when doing my makeup so I do it topless hope you don’t mind. Mary came in and pretended to be picking out clothes to wear but really she was watching Michelle’s breasts and getting very turned on. She didn’t really understand why she felt this way, but she did. She told me she fantasized about sucking on Michelle’s nipples for weeks and felt very guilty about it. She also told me when her parents were out black friday shopping Michelle and her older brother fucked like rabbits and she heard the whole thing. She masturbated constantly listening to them and wanting to be the one and fantasizing about fucking Michelle. She was so sexually charged and horny she was masturbating 7 or 8 times a day for weeks.
A few months later there was a guy at her school that really liked Mary and asked her to their spring dance. She had been taught her whole life that being gay was a sin and gays went to hell that she was determined to make herself attracted to men and figured why not say yes and experiment with him. They went to the dance together and then “parked” at the park which is where couples from high school went to make-out or fuck in cars. She told me he was touching her pussy and she closed her eyes and was picturing Michelle touching her pussy and she came so hard. This guy thought he was the shit for getting her off so fast, but really it was because of her fantasies. She told me she liked the way he touched her she just wasn’t super attracted to him but she thought she could make this work and would just fantasize but live the “normal life”. This went on for almost a year she even let him fuck her all the time but would fantasize about Michelle or her friend Justine from swim team who she frequently saw naked changing out of their swimsuits.
When Mary was a sophomore in high school she won some state championship for swimming and was asked to try out for the Olympics (she never made it but you don’t care that’s not why you’re reading this story ;)). Mary went to a training camp in southern California to train with other girls her age. One of her coaches was a woman named Barbara who was in her mid 30s but Mary thought she was extremely sexy and loved watching her change secretly. Mary said she always felt like a perv secretly watching but she said it helped her keep up her “facade” so she could fantasize when she was with guys. About a month into training camp Barbara called Mary into her office to talk to her. Barbara mentioned that she saw Mary looking at her when she was changing and asked if she was a lesbian. Mary denied it up and down. Barbara looked at her and Mary said she might be attracted to women but she didn’t want to live that way and didn’t want to go to hell. Barbara confided in Mary and told Mary she was a lesbian and lived with a woman. Barbara told Mary anytime that Mary wanted to talk about it she was welcome to talk to Barbara and that she wouldn’t go to hell and there was nothing wrong with her feelings. Mary opened up and told her everything about Michelle about Justine about this guy she had been dating over a year that she was having sex with but fantasizing about women while doing so.
Barbara took Mary to a Gay and Lesbian teen center that was run by a non profit so Mary could meet other young gay people. That is where Mary met Jasmine who was an 18 year old lesbian from the area. They became friends and then more than friends. Mary said the first time her and Jasmine were intimate it was like fireworks went off. She told me Jasmine was the one that taught her about clit sucking. And about sex toys and being comfortable with her sexuality. Jasmine was a senior in HS and was about to graduate and was heading to Smith College in Massachusetts. Mary didn’t know a thing about Massachusetts or Smith College but she decided that is where she wanted to go. She wanted to be anywhere that Jasmine was. Mary ended up going back to Georgia. This is pre-internet (this was probably in 1991/92) so Mary promised Jasmine she would open up a PO Box somewhere so they could write each other letters. The wrote each other almost everyday. Mary said she got a job at an office supply store in her town just because they had PO Boxes and she could get a discount. Mary showed me some of the letters they were very erotic.
Mary didn’t get into Smith but she did get into a university in Boston. Unfortunately her and Jasmine drifted apart but Mary found her first lesbian club/hang out when she was a freshman in college and went wild. She had an affair with a 40 year old stay at home Mom named Donna. Mary would go to her house after class and they would eat each others pussies and fuck each other with toys until Donna’s husband came home. She told me that when her son was watching cartoons her and Donna would go into another room and fuck each other with toys or even put vibrators in their panties and sit on the couch out by her son and orgasm quietly. She told me that Donna used to hire a trans prostitute sometimes that still had her cock and could get it hard but had these huge fake tits. Donna loved getting fucked by the prostitute and playing with her tits.
When Mary was finished telling me these stories we were both really horny again. I asked Mary what other toys she had. Mary told me to me to come with her and we went into her closet and in the bottom of her closet was one of those big Rubbermaid bins filled with sex toys. Some brand new. In the bin I found what looked like a strap on device but instead of having a cock it had something that looked like a butterfly. I pulled that out and asked Mary what it was for. She told me to put it on. I pulled the straps up my legs and the butterfly sat against my pussy. I saw Mary fish around the bin of toys for something else and she pulled out a purple thing on a key chain. She put a battery in it and hit a button. All of the sudden the butterfly was vibrating against my pussy. She could control the vibrations. As soon as it started to feel good she turned it off. I told her she was a tease. I must have told her at some point that Tim and I sometimes had phone sex and she told me to call Tim and get him horny and she would turn the vibe on and make me cum while listening to him jerk off. I told her I had a better idea. I said sometimes Tim and I use the webcam feature on AIM and I could tell him I got a new toy and you can control from the closet where he can’t see you but you’ll be able to watch him jerk off. Mary thought that was so hot. She grabbed my hand and basically dragged me to my bedroom.
I turned on my computer and saw Tim was online but away I IM’d him but no reply so I called him and said I wanted to go on webcam for him. He said give him 10 minutes. He called me back and told me he kicked a few of his law school buddies out of his room. He told me to turn on my cam. I did and he asked what I was wearing I told him it was a new vibrator I bought the other day. I laid on my back on the bed and faced the cam towards my body so he could see all of me. I told him I wanted to put him on speaker so I could play with my nipples also while I listened but really it was so Mary could hear him. I saw him turn on his cam and made it so it took up my whole screen so Mary could see his thick cock. He said you have me so hard and you’re such a naughty girl. Mary turned the vibe on and I moaned. He said ooh that vibe must feel good on your pussy. How about I fuck you with the vibe on. I bet you’d cum a few times on my cock. Mary slowed it and I grabbed the sheets out of frustration but it also felt so good. Mary turned the vibe on a different setting that was pulsing against my clit. That sensation made me start panting and moaning.
Tim was stroking really fast listening to me. He was saying things like I bet you wish my cock was in you and I bet you wish that was my tongue. I couldn’t take it I was so close but I needed it faster. I started arching my back and grabbing my sheets. Tim was watching and was saying oh yes that’s what you look like when I tease your clit. Yes tease your clit baby. Tease it like I would tease it with my tongue and my cock. Mary adjusted the setting again and it felt almost like a roller coaster on my clit it went slow like it was going up hill but it was strong then it did a long series of buzzes and then it went into fast buzzes. This was getting me there quickly. I was so close. I grabbed my sheets and nearly pulled them off the bed and started shaking. Tim was saying oh yes you’re close I can tell your thighs are quivering. That’s how I know you’re going to explode. Let it go baby. The next round after the slow speed when it got to the buzzing I started cumming. I yelled I’m cumming. Tim was stroking his cock fast. He said oh fuck I need that tight pussy. I can’t wait until next weekend I’m going to cum in you constantly and fill that pussy up. I saw him tilt his head back and then a spurt of cum came out of his cock then another and another. Tim started laughing and said my girlfriend is so naughty and I love it. I could barely move I was in another orgasm coma I felt like. I could barely speak. Tim was laughing at me but told me he had to go he had a big exam coming up and needed to get back to his study group. We told each other we loved each other and would talk soon. I heard his phone click and saw his webcam shut off. I did the same.
Mary came out of my closet and told me how hot she thought that was. She pulled the toy off my pussy and buried her face in between my legs and cleaned up all my juices. She had the strap on and put it on and positioned the dildo cock near my whole and asked if I was ready I said yes. She turned on the vibe fast I could feel it as she fucked me with her fake cock. She pushed my legs back and pounded me. She started saying oh fuck yes I want Tim to watch me fuck you. I want him to watch a girl fuck your pussy. She was shaking and said I’m cumming and the vibrations of the dildo started to make me cum and I came on her fake cock. We both could barely move and giggled and cuddled in my bed.
Source: reddit.com/r/gonewildstories/comments/ejra97/ff_my_first_time_with_a_woman_my_roommate_part_3
Please let there be a part 4