[M]y girlfriend traded her Anal Virginity for a Property In Monopoly

This story happened with my ex girlfriend. Super skinny brunette. Small tits. Gorgeous face. Long Legs. We were both in university. She was 20, I was 24. She was a super fit dancer, and I thought she could easily be a model. By the time this story takes place we had been dating for 6 months and having sex pretty much since the first night we met. She had some past relationships but was mostly inexperienced. I didn’t take her virginity and at the time it was something I felt amiss about.

I had suggested I take her anal virginity but she was not into it. I never pushed it further, but I did try and massage her butt hole whenever I got the chance. She usually pushed me away and we just moved on. I pretty much stopped asking for anal at this point.

I lived alone, while she lived in a house with 5 other people. That night, we were at her house and were playing Monopoly with her roommates. We were all drinking, and having quite a bit of fun. After an hour or two into the game, most people started setting up houses/hotels, and it was clear who was leading in the game. My girlfriend didn’t have enough matching properties to put up houses/hotels. She had 2 of the green properties, and was missing the 3rd and final piece, the one piece I had.

She asked me with her sweet and cute voice if I could give her the final green property she needed. I said NO WAY, if I do I’ll lose. She took out her phone to be discreet from her roommates and texted saying she’d give me a blow job later if I did. Tempting, but I was use to getting blowjobs regularly so it wasn’t anything that peaked my interest. I turned down the offer.

After another turn around GO, the game really heated up. Her roommates were clearly winning and showing off about it. At this point she was getting more determined to win. She then texted the magic words “I’ll do anything”.

Of course I am beyond excited, but knew I had to play it cool. I replied “what do you have in mind?”. At this point she put her phone down, sat on my lap, and whispered in my ear “you can put it in my ass tonight”. As she says this, she sticks her tongue in my ear and gives me a quick kiss.

I immediately produced the biggest grin of my life and handed over the green property. The other people playing the game all started screaming, and wondering WTF. Her and I both knew, but we kept it to ourselves. I suspect they knew she made a really good trade for that card, but no one probed further.

She eventually got to put up hotels, but still lost the game. As the night concluded, her and I left to head back to my place. She had her own place and we would often fuck there, mostly as an afternoon quickie between classes. She slept at my place pretty much every night because I lived alone and she was a bit loud in bed.

The drive home was mostly quiet. We made small chit chat, mostly about her friends. Neither of us brought up our arrangement. She did rest her hand on my dick while driving, which is something she always did.

When we got to my apartment, the moment we walked through the door I pinned her against the wall and starting kissing her, HARD. This was pretty common for us. I usually couldn’t wait to get her home to fuck. Right by the entrance to the door we are still making out and I am kissing her neck. She loves when I kiss her neck.

We peel each others clothes off as we make our way to the bedroom. While standing naked, and making out I squeeze her ass and massage her asshole a bit. She was a bit squirmish, and moved my hand from her ass to her hips. She then proceeds to lay on the bed. With me on top of her, both naked, I pause and I tell her “I love you, and we dont actually have to have anal sex tonight. I just want you to be comfortable”.

I guess this is what she really needed to hear. At that point she says “NO, a deal is a deal. I want you to fuck my ass. Just be gentle, and don’t take your time”. My dick was so hard at this point I could barely hold back from cumming. Of course I say “are you sure?”, to which she responds with a deep passionate kiss.

We are making out with me on top. I slide my fingers in her pussy. She is soaking wet. I slowly finger her while she moans loudly. She tells me how much she loves it. I pull my fingers out of her dripping wet pussy and put them in my mouth to taste all her juices. She loves seeing me do this because she knows what comes next. I move down and stick my tongue as far inside her pussy as I can. She lets out a YELP. I then move to her clit and slowly caress it with my tongue. I can tell her orgasm is building, but I knew the moment she cums her energy for the moment will go down.

I stop and motion her body to flip over so she is lying on her stomach. While she lyes on her stomach, I continue to lick her pussy, but move my way up to her ass. I slide my tongue around her ass and slowly try sliding my tongue in side. She was a bit squimish but I can tell she liked it. I alternated between eating her pussy and fingering her ass, or just eating her ass.

After a short while she starts begging me to fuck her. She screams “I need your dick inside me..Please fuck me”. I stop what I am doing and with her still on her stomach, I move my dick to her pussy and slide right in. I begin fucking her prone bone, very slow at first. She takes a moment to adjust having me all the way inside her…. Then she says “ohhh fuck me harder”. I knew that was my que to pound away. I start moving my hips and pounding her really hard. She is loving it. After about a minute my cock was about to explode, I had to slide out of her and use all my power to hold back from cumming.

She didn’t know I slid out of her because I was about to cum, she instead said “Is it time? Are you ready to fuck my ass and go where no man has gone before.” I love how she talks dirty to me when she is really horny. I lean in and give her ass a quick lick.

I reach over to our night stand where we have a sex drawer. It includes a vibrator, naked photos, condoms which we never use because I just cum all over her instead, and lube. I grab the lube, squirt some on my fingers and start spreading it in her ass. I finger her ass slowly with my lubed up fingers, and also apply a fair amount of lube on my dick.

She then moved to the spooning position and suggested this way might be easier for her. I lye beside her and try to align my cock with the entry to her ass. I guess I was moving too slowly as she then reaches back and grabs my cock and aligns it perfectly with her ass. I push in slowly, while she holds my cock and guides it in. I break through and get my tip in pretty quickly. She says it hurts a bit. I suggested we stop, but she was determined and says “No, I need you”. We pause and just lay there with the tip of my cock inside her for a minute or two. She eventually relaxes and says the pain went away. I proceeded to slide further in slowly. It took about a minute to slide in another inch, pause for her to adjust, and then slide in another inch. Eventually I got my entire cock inside her ass. IT FELT LIKE HEAVEN. She was sooo tight, and the taboo nature of what we were doing really turned me on.

At this point I asked if she is OK. She said “Yes fuck me..but hurry”. We are still in the spooning position. I begin moving in and out of her ass. Slowly at first, but I quickly picked up the pace as I can tell she was beginning to enjoy it. She would shout “Yes”, and “Thats it”, and “Oh God”, and “Dont stop’. It was incredible. I then placed one hand so it would massage her perfectly small breasts, and the other wrapped around her so I could massage her clit.

This must of sent her over the age. As I rubber the juices from her dripping wet pussy over to her clit and slid in and out of her ass she began shaking like she never has before. She begins screaming “FUCK ME HARDER”, and “OH YES FUCK ME”, “FUCK MY ASS”. I begin pounding her ass as hard as I can. I then roll her from the spooning position back to prone bone with my cock still in her ass. In prone bone I had my hands over hers and she was pinned down. Her clit was against the comforter and was rubbing against it as I was moving in and out.

I begin fucking her with all my strength. I was doing everything I could to hold back from cumming, but she eventually screamed “FUCCCCKK” and had an intense orgasm. In this moment she squeezed her anus muscles and I just couldn’t resist. I also screamed ” I AM CUMMING”. She responds “GIVE ME YOUR CUM. CUM INSIDE MY ASS”. I let out rope after rope of my hot cum into her. It felts so good. I then collapsed on top of her. My cock still in her ass, twitching.

We were both a huge sweaty mess. The room smelled of sex and sweat. We were both exhausted and just catching our breath. My cock eventually got soft and she pushed it out of her with her anal flexes. We didnt say a word, we just moved to the spooning position where I held her the whole night while we slept.

When we woke in the morning we were both a sticky mess from the lube, sweat, and pussy juice. I asked how was last night, and if she would do it again. She shoved her tongue down my mouth and said “You bet my ass I would”.

Source: reddit.com/r/gonewildstories/comments/fl9hvx/my_girlfriend_traded_her_anal_virginity_for_a