Anal Virgin No More - Bedroom Fantasies #80

This story happened with my ex-girlfriend. Slim brunette, B-cups, gorgeous face, and long legs. We were both in uni. 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'd 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 asshole whenever I got the chance. She wasn’t very receptive to this, so eventually I stopped trying.

I lived alone while she lived in a house with five other people. That night, we were at her house and were playing Monopoly with her housemates. We were all drinking and having a great time. 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 three houses, and was missing the final piece, the one piece I had.

She asked me with her sweet and sultry voice if I could give her the final house 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 blowjob later if I did. Tempting, but I was used to getting blowjobs regularly, so it wasn't anything that piqued my interest.

After another turn around GO, the game really heated up. Her roommates were clearly winning and becoming very boisterous. At this point she was getting more determined to win. Out came her phone, and soon the magic words: "I'll do anything".

Of course, I was 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 said this, she stuck her tongue in my ear and gave me a quick kiss.

A huge grin crept across my face and I immediately handed over the green property. Her housemates started screaming and protesting. She and I both knew, but we kept it to ourselves. I suspect they knew she made an exchange outside of the game, but no one probed further.

She eventually got to put up hotels, but still lost the game. As the night concluded, she and I left to head back to my place. 

The drive home was mostly quiet. We made small chitchat, 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 started kissing her, HARD. This was common for us. I usually couldn't wait to get her home and straight to the bedroom.

We peeled each other’s clothes off as we made our way down the hall. While standing naked and making out, I squeezed her ass and massaged her asshole a bit. She was a bit squeamish 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 don’t actually have to have anal sex tonight. I just want you to be comfortable."

I guess this was what she really needed to hear. At that point, she said, "NO, a deal is a deal. I want you to pound my ass." My dick was so hard at this point I could barely hold back from cumming. 

We were making out with me on top. I slid my fingers in her pussy. She was soaking wet. I slowly increased the pace while she moaned loudly. She told me how much she loved it. I pulled my fingers out of her dripping wet pussy and put them in my mouth to taste all her juices. She loved seeing me do this because she knew what came next. I moved down and stuck my tongue as far inside her pussy as I could. She lets out a YELP. I then moved to her clit and slowly caressed it with my tongue. I could tell her orgasm is building, but I knew the moment she climaxed, her energy for the moment would go down.

I stopped and motioned her to flip over so she was lying on her stomach, prone bone. While she lay there, I continued to lick her pussy, but moved my way up to her ass. I slid my tongue around her hole and slowly tried slipping my tongue inside. She let out a small gasp.

After a short while she started begging me to enter her. She screamed, "I need your dick inside me!" I stopped what I was doing and, with her still on her stomach, I moved my dick to her pussy and slid right in. I began gliding inside her, very slow at first. She took a moment to adjust to having me all the way inside her. Then she said, "Ohhh, harder!" I knew that was my cue to pound away. I started moving my hips with explosive force. She was loving it. After about a minute my cock was about to explode, I had to slide out of her and use all my will to hold back from finishing.

She didn't know I'd slid out of her because I was about to cum. Instead, she asked, "Is it time? Are you ready to take my ass and go where no man has gone before?"

I loved how she talked dirty to me when she was really horny. I leaned in and gave her ass a quick lick.

I reached over to our nightstand and grabbed the lube, squirting some on my fingers and started spreading it around. I fingered her ass slowly with my lubed up fingers, slowly stretching her out.

She then moved to the spooning position and suggested this way might be easier for her. I lay beside her and tried to align my cock with the entry to her ass. I guess I was moving too slowly as she then reached back, grabbing my cock and aligning it perfectly. I pushed in slowly while she guided me in with her hand. I broke through and got my tip in quickly; she let out a small whimper. I suggested we stop, but she was determined and said, "No, I need you."

We paused and just lay there with the tip of my cock inside her for a minute or two. She eventually relaxed and gave me a signal to go. 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 of her. This was different, she was so tight, and the taboo nature of what we were doing took control of my thoughts.

I asked if she was OK. She responded with, "Yes, hurry up!" I began moving in and out of her ass. Slowly at first, but I quickly picked up the pace as I could tell she was beginning to enjoy it. She would shout "yes", and "that’s it", and "oh God", and "don’t 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 have sent her over the edge. As I rubbed 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 had before. She began screaming, "HARDER, DON’T STOP, FILL MY ASS!" I began pounding her ass as hard as I could. I then rolled her from the spooning position back to prone bone with my cock still inside. I had my hands over hers, pinning her down. Her clit was against the comforter and was rubbing against it as I was moving in and out.

I began thrusting with all my strength. I was doing everything I could to hold back from cumming, but she eventually screamed and began shaking with an intense orgasm. In this moment, she squeezed her anus muscles and I just couldn't resist. She responded, "GIVE ME YOUR CUM, CUM INSIDE MY ASS!" I let out rope after rope of my hot cum into her. It felt 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. We didn’t say a word, we just moved to the spooning position where I held her the whole night while we slept in complete bliss.

Submitted by MSG from Nunawading, Victoria, Australia

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