[FF] My First Time with a Woman (my roommate)

This story takes place back in 2006 during a huge blizzard we had in the northeast. I recently told my husband this story and he encouraged me to share here since we sometimes read this subreddit for inspiration ;-)

In September 2005 I was 23, had my first job and was looking for my first apartment. Based on what I was earning I knew I’d likely need a roommate. The company I worked for at the time had a bulletin board in our kitchen where people could post things like they were looking to sell their car or find a roommate or sell off their timeshare. You get the point. I decided to have a look on the board and saw a woman named Mary was looking for a roommate to share her two bedroom condo with and it was right in my price range. I worked at a huge pharma company so I had no idea who this woman was, but I looked her up in the directory and sent her an email. She worked in the same building as me but on a different floor and she said she would stop down during lunch time. Mary looked to be about 30, had a short pixi cut, light brown hair, a very thin small frame that was covered by a button down shirt and khaki pants. She told me about the apartment and showed me some pictures from her digital camera and told me it was available immediately as her last roommate just moved out. The price range was exactly what I was looking for and I’d have my own bedroom and bathroom, the kitchen and living room would be shared. She told me I could swing by after work and check out the place if I was interested. I ended up loving it and signing a 18 month agreement with her because I knew in a year my boyfriend at the time would be finished with law school and he promised we’d get a place together.

Fast forward a few months, I had been living with Mary for a few months and we had become friendly. When my boyfriend came to visit we’d generally like hanging out with her. I even mentioned to my boyfriend a few times that I wanted to set her up with his friend Chris from law school. My boyfriend would just laugh at me and say I don’t think that’s a good idea. When I asked why he said I think your roomie plays on the same team as me. I was like no way. He was like yeah I see the way she looks at you. Yesterday when you were walking around in your tank top and panties I know she was looking at your nipples because I was looking at your nipples. I laughed it off and didn’t think much about it.

A few weeks later my boyfriend was supposed to come visit for the weekend (it was the weekend before valentines day of 2006) but they were predicting a massive blizzard for the NE and he was afraid he wouldn’t be able to get back to school for an exam so he said he would come down after Vday and take me out for a special night. That Friday night I was bumming around the condo kind of moping that my bf wasn’t coming down for the weekend when Mary asked if Tim was coming down. I told her the whole story and that I understood but I hated going almost a month without seeing each other. She said she was heading down to the video rental place (it was a local chain kind of like blockbuster remember them?!) and asked if I wanted to come that she was going to rent some DVD’s since we’d likely be trapped in the condo for the weekend since they were predicting like 30″ of snow. We rented a bunch of DVD’s stopped and got a ton of junk food, some beer and wine, and decided we’d camp out in the living room for the weekend, eat junk food and hang out.

About two movies into our living room camp out we decided to take a break from movies and just chill. Mary also had some weed so we smoked a bowl together. One puff in I blurted out…Are you a lesbian? I was so embarrassed after I did that, I was blushing and apologizing. She laughed at me and said yes I am. I hope that doesn’t bother you. I swore up and down it didn’t, I was just curious because I never had a lesbian friend before and I had this stereotype in my head that they were man hating straight woman hating people and Mary was none of those things. She was super nice and got along with pretty much everyone she met. We spent the remainder of the evening watching snow fall, drinking too much wine and just talking about everything. I realized even though we lived together for about 4 months I knew very little about her other than she was originally from Georgia, wasn’t super close to her family and came to the NE for college, got a job here and never looked back. She told me about coming out, about how she got kicked out and how her last roommate wasn’t really her roommate but her last girlfriend and they broke up.

I was pretty tipsy and a bit high and I blurted out (again) do you look at my nipples? Tim thinks you look at my nipples. She told me he wasn’t wrong and that she thought I had a beautiful body. I asked if it made her uncomfortable that I walked around in tank tops and panties a lot. She said she liked it as long as it didn’t make me uncomfortable now that I know she’s attracted to women. I was very curious about lesbian sex. I had seen some porn with my boyfriend and it definitely turned me on, I never shared that with anyone before. We started talking about sex and what we liked and didn’t like. I told her that I loved when my BF went down on me. She told me she knew that because she could hear me moaning and wimpering but didn’t hear the bed so she knew what he was doing.

That night we fell asleep on the couch together and I woke up the next morning to being cuddled under the covers with her. We were both in T-shirt’s and panties and I loved feeling her soft legs against mine. She was still sleeping but I remember thinking that I wanted to kiss her. So I gently kissed her lips. And she woke up. She kissed me back. We kissed for a little bit. I told her that I was attracted to her but loved my boyfriend. And that I would be interested in experimenting. We started kissing and touching. We took off our tops and started touching each other’s nipples. I have large breasts (36D) and she had small breasts (34A) but super pointy long nipples. I pinched them and she arched her back. I sucked one into my mouth and she moaned.

She pushed me onto my back and kissed my neck and my breasts and sucked on my nipples. I was so horny by this point I was whimpering. She reached into my panties and started to play with my clit. I was so horny I almost came but she stopped when I got close to Cumming. She pulled down my panties as well as hers. We were kissing again and she was laying in between my legs. She moved so her pelvis was rubbing against my clit. She was sucking my nipples at the same time. It felt so good. I got close and she started rubbing my clit fast and I came.

She kept rubbing my clit even though it was so sensitive and then I had another orgasm. She slid down my body and started nibbling on my pussy lips. Sucking on them. Then she sucked my clit into her mouth. I had oral sex before but no one ever did this to me before. My legs were quivering and she wouldn’t let up and I had a super intense orgasm. I was laying on the couch naked and super spent and breathing heavy. I could barely move and I dozed off.

If you like this I’ll give you a part 2;).

Source: reddit.com/r/gonewildstories/comments/ei4665/ff_my_first_time_with_a_woman_my_roommate

20 comments

  1. I hope you feel moved to share more. I enjoyed your story, the style in which you wrote it, and it left me at a climatic cliff hanger…thank you!

  2. A minor question, was your boyfriend at the time your now husband or did this affect you and your boyfriend at all? Sorry if this seems like an odd question, I’m just curious

  3. I’m also a 36 D. I thought i had pretty average breasts… maybe they don’t look too big on me cause I’m 5’6” and 160 lbs

  4. Did you live in NYC?
    In my head, as you told this story, I kept on thinking it was Kim’s Video you guys walked to..

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