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C|Suite Letters: A Monopoly Over Dat Ass

C|Suite is a men's magazine founded by Frank Cervi. It combines urban/office life-style articles with soft-core pornographic pictorials. In recent years, C-Suite introduced the 'letters' column in which readers send in borderline ridiculous sexcapades, resulting often in explicit and unnecessary detail.


Dear C|Suite,

I never thought the day would come, but it finally did; My girlfriend and I came as well, just so ya’ll know.

It took so long!

How can one describe such a magnificent piece-of-ass: Super skinny brunette, decent tits, gorgeous face, and long legs. We are both in university. She is nineteen, I am twenty-four. She is a super fit dancer, and I think she could easily be a model.

By the time this story took place we had been dating for about five days and having sex pretty much since the first night we met. She had some past relationships but she was mostly inexperienced in my opinion. I hadn't taken her anal virginity yet, 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. So for those whole, long and frustrating five days, all we did was have normal, penis-pounding-vagina sex; it was a real disappointment. I never pushed it further, but I did try and massage her asshole whenever I got the opportunity. She would frequently push me away and we’d just moved on. I pretty much stopped asking for anal at this point.

I live alone, while she lives in a house with six other people.

Just the other night, magic had finally happened.

We were at her house and were playing Monopoly by Hasbro 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 obvious who was leading in the game. My girlfriend didn't have enough matching properties to put up houses/hotels. She had two of the green properties, and was missing the third and final piece, the one piece I had.

She asked me with her soft, 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 in order to be discreet from her roommates and texted me 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 aroused my interest. I turned the offer down, naturally. I could get blown no problem if I wanted to. I could just go down to the corner of 5th and Fitch with $5 in hand for one of those behind the Denny’s specials from one of the wayward girls trying to make a buck for some cigs. Oh, and yeah, I guess I could always just ask my girlfriend as well for a suck and dry.


After another turn around GO, the game really started to heat up. Her roommates were clearly winning and showing off about it. At this point my girlfriend was getting more determined to win due to the jealously and not being able to “keep-up with the Jones’” on the board. She then texted me the magic words, "I'll do anything".

Of course I was beyond excited at this point, but I knew I had to play it cool. I replied with, "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 thereafter.

I immediately produced the biggest grin of my life and handed over the green property, without hesitation.

The other people playing the game all started screaming, and wondering ‘what the fuck!’ My girlfriend and I both knew, but we kept it to ourselves. I suspected they [her friends] knew she made a really good trade for that card, but no one probed further. The only probing that was going to be done that night was by me.

My girlfriend eventually got to put up hotels, however in the end still lost the game. As ‘game night’ concluded, she and I left to head back to my place. The real games were about to begin; I was going to go through the ‘back door to her house’ instead of the front, if you know what I mean.

The drive home was mostly quiet. We made small chit-chat, mostly about her friends and how she hated them.

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 were still making out and I was kissing her neck. She loves when I kiss her neck. It makes her eyes glow like Irish fields after a morning’s rain; her pussy, wet, like those said fields.

We peeled each other’s clothes off as we made our way to the bedroom. 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 proceeded to lay on the bed, with me on top of her. Both naked, I paused and I told her "I love yo—your ass, and we don’t actually have to have sex tonight like usual. I just want you to be comfortable doing just anal….sex".

In hindsight, I guess this is what she really needed to hear. At that point she said "Yes, 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 then asked, "Are you sure?", to which she responded with a deep, passionate kiss.

We were making out with me on top by this point. I had slid my fingers into her pussy. She was soaking wet, like small a divot on the fairway of an Irish golf course….after a….evening’s rain.

I slowly fingered her while she moaned loudly. She told me how much she loved it. I pulled my fingers out of her dripping wet pussy…like how one would pull theirs out of the wet tin cup of the 18th hole of that Irish golf course; I round well played, soaking wet.

I then put those same wet, sticky fingers in my mouth to taste all her juices. She loved seeing me do this because she knew what would come next. I moved down and stuck my tongue as far inside her pussy as I could. She let out a yelp; not a full review, but meaningful nonetheless. I then moved to her clit and slowly caressed it with my tongue. I could tell her orgasm was building, but I knew the moment she cums her energy for the moment would go down.

I stopped and motioned her body to flip over so she would be lying on her stomach. While she laid on her stomach like a day at the beach, I continued to lick her pussy, but then slowly moved my way up to her ass.

I slid my tongue around her ass and slowly tried sliding it inside. She was a bit squeamish, yet again, but I could tell she liked it. I alternated between eating her pussy and fingering her asshole, or just eating her ass.

After a short while she started begging me to fuck her. She screamed, "I need your dick inside me..please fuck me!". I stopped what I was doing and with her still on her stomach, I positioned my dick near her pussy and slid right in. I began fucking her prone bone, very slow at first. She took a moment to adjust having me all the way inside her.

Then she let out a, "Ohhh fuck me harder". I knew that was my que to pound away. I started moving my hips and pounding her really hard. She was lovin’ every minute of it to quote Loverboy.

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 at the time that I’d slid out of her, because I was about to cum, she instead figured, "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.

Anyways, I then leaned in and gave her ass a quick lick.

I reached over to my 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 grabbed the lube, squirted some on my fingers and started spreading it in her ass. I fingered her ass slowly with my lubed up fingers, and also applied 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 then laid beside her and tried to align my cock with the entry to her asshole. I guess I was moving too slowly as she then reached back and decided to grab my cock and aligned it perfectly with her asshole. I pushed in slowly, while she held my cock to guide it in. I broke through; got my tip in pretty quickly to hear that lovely squish sound. She said it hurts a bit.’ Feelings are subject to personal interpretation; it didn’t hurt me.

I suggested we stop, but she was determined and said, "No, I need you". She is a special kind of woman.

We paused and just liad there with the tip of my cock inside her for a minute or two. She eventually relaxed and told me that the pain went away. I proceeded to slide further in, slowly. It took about a minute to slide in another inch, pausing for her to adjust, and then slide in another inch. Eventually I got my entire cock inside her ass!


She was sooo tight unlike her pussy, and the taboo nature of what we were doing really turned me on.

At this point I asked if she was OK. She said, "Yes fuck me..but hurry". We were still in the spooning position. I began moving in and out of her asshole. Slowly at first, but I quickly picked up the pace as I could tell she was beginning to enjoy it immensely. She would shout "Yes", and "That’s it", and "Oh God", and "Don’t stop'. All were very consensual words and phrases, yes.

It was incredible. I then placed one hand so it would massage her perfectly ample breasts, and the other wrapped around her so I could massage her clit, of course.

This must have sent her over the age. 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, "FUCK ME HARDER", and "OH YES FUCK ME", "FUCK MY ASS". I began pounding her ass as harder than any gay dude could ever.

I then rolled 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 began 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. Her face looked like it normally does when she’s at the mall buying brand name shoes at 30% off.

In this moment she squeezed her anus muscles and I just couldn't resist. I blasted the white devil inside her hell hole.

She responded, "Give me your cum..cum inside my ass!". Rope after rope of my white, hot cocoa-cum into her. It felt so good. I then collapsed on top of her. My cock was still in her ass, twitching.

We were both a tangled sweaty mess. The room smelled of sex, sweat…and ass. 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. Such a fit-chick.

We didn’t 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 mixed with ass tang. I asked how last night was, and if she would do it again. She shoved her tongue down my mouth (French style) and then upon un-hooking said tongue out from my mouth said, "You bet my ass I would".

Yours truly horny,

Mr. Monopoly


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