The perils of being a former (really?) slut

The aforementioned A started talking to me again on Sunday. I believe this will require some backstory.

We met online, in September, I believe, and I found out that he only lives a few blocks from me, and we have a couple of vague mutual friends. (This town is small.) From chatting online, I discovered he was really looking for a relationship, and I wasn't at the time. (I wasn't at the time I started dating M either, but that's another story.) But, he wanted to hang out and one thing lead to another and we had a pretty good NSA thing going, but I could feel him starting to get attached, which made me freak out because I didn't want to hurt anyone else, I just wanted to have good consistent sex with someone that I was friends with. Apparently this is too much to ask.

Well, we were fucking for about 3 months non-exclusively, and it was excellent sex. Then the college quarter ended right before Thanksgiving, and he just disappeared. Didn't answer phone calls or texts, and was never online (he used to be online every day, almost all day). Of course, I didn't call or text that often, as I wasn't really supposed to be keeping tabs on him, but when we saw each other frequently and then there was NOTHING, it made me wonder what that fuck was going on. And I think I realized that I did have some feelings for him...I guess it's true that you don't know what you've got 'til it's gone. The sex with him was somehow different than what I had previously experienced. He was kind of a switch...he loved to be dominated, but also could pull a number on me as well.

Anyway, my last text to him in mid December said something to the effect of "Just wanted to make sure you're still alive." Two weeks later I get a drunken phone call at 3am so he could tell me he was still alive, and that he needed to go pass out. Later, I never did get out of him why he disappeared, but I said we could stay friends. We had one good conversation after that on the phone about sex, where I learned about his ex that used to lead him around by a leash around his balls, and his affinity for leather. Then he sorta disappeared again and called me once around the time M and I started dating in early February. I posed the idea to M of an open relationship, as A had expressed interest in fucking me again, but M's a little too traditional for such things, so I made a conscious effort to try to forget about A and delve into my relationship with M. And I was completely successful. Until Sunday.

A tried to explain to me why he disappeared, but still didn't have a concrete reason...I think if I hadn't been so anti-relationship at the time, A and I would have ended up in one. He finally did apologize for dropping off the face of earth (I think he finally realized how much that sucked for me) and that he missed hanging out with me and wanted to still be friends. I've tried being friends with former fuck-buddies before, and it's difficult to say in the least. Still, I told him that I would hang out with him the next day. He never showed...something about a huge family argument. But still he got me thinking...

A's cock is thicker than M's, and while he hadn't used it in quite the same ways as M, there's something to be said about a more bulbous cockhead massaging you from the inside. I began to think about how easy it would have been to fuck him silly with all my roommates being away, and M would never know. I try so hard at this monogamy thing, but I just don't think I'm cut out for it. Maybe it's best that A didn't show up.

Then there's the story of C. I can't even remember how I ever got talking to this guy about sex, but I know that we spent several conversations skipping out of work or over a drink after work discussing relationships and sex and the pros and cons of seeing multiple people at once (as that was what I was attempting at the time) and we realized that we had a mutual attraction, but he was (and still is) in a relatively stable relationship and has been for over 2 years. He's significantly older, which to me only meant that he was more experienced, which made him all that more attractive. Aside from one time where we kissed in his office, it had all been teasing and sending of pictures and such. I was not about to be a homewrecker, and his office did not allow for a whole lot of privacy. Until today, when somehow I ended up in the basement of his office.

I fell for the line "You have to pee, don't you? Let me show you where the bathroom is." So I followed him down the stairs, and he went into the one stall of the bathroom, and guided me in with him and said, "Now go pee." He kissed me, and in between kisses, I asked him what his fascination with urination was. Up until this point, I had never known a guy personally that was interested in such things. I told him it was awkward, but yet I still undid my belt and took my pants down and sat down. This of course put my face right in front of his cock...he was quick to undo his pants as well. It was as beautiful as I had seen in pictures...deliciously thick. Without thinking, I took his hardening cock into my mouth. As he got harder, I wrapped my hand around his shaft as I tried to take him in as deeply as I could. He moaned, and said I should pee, and I didn't think I could so I just kept sucking. He told me to turn around but I declined, mentioning that he had bad timing. He then said he could put it in my ass, and while the thought was tempting, I knew he was too big for ass fucking without lube, and I told him so. He mentioned saliva, but I shook my head no. He then undid his pants all the way and pulled them down a bit...I was then able to reach under his balls...every man loves that spot just beneath them. After a few more deep sucks and concentrating on his large cockhead with my tongue, he came more quickly than I had expected, and tasted delicious. I kept sucking on the head and just below it as he came, making sure I had gotten all of his sticky juices. He was stifling moans...I think my cocksucking talent surprised him. He told me that he didn't know what it was about me, but that he hadn't been "bad, like really bad" like that in a long time. I smiled...it was good to know I still have some appeal. He put himself back together, and realized that me peeing in front of him wasn't going to happen, so he stepped out for a moment while I did my business. When I came out, he was like "Ok, the story is that you were trying to sell me drugs, and that we were haggling about pricing, and that's why we were in the bathroom with the door shut. Ok, cool." And then he changed the subject and we walked up the stairs and went back to his office as though nothing had happened.

So much for monogamy. Did I mention that M used to work for C? And that it's M's birthday? A new low, yet I surprisingly don't feel that horrible.

Weekend...

Spent the weekend with M. It was that time of the month...really for me, every three months (the wonders of modern medicine!) so we were pretty chill. It was nice to just spend some time together.

However, when we went to bed Friday night, I wasn't really able to sleep. I didn't really realize it was because I was horny, but M seemed to put it together. After much tossing and turning in the middle of the night (around 4am), we ended up in a spooning position, and he ever so gently began to caress my breasts. A little more movement from him caused some motion from me, mostly my ass beginning to rub against his hardening cock. His hand moved lower, beginning to rub my crotch through my panties, his lips finding my neck. I moaned softly as I rubbed harder against him, alternating between pressing against his hand and his cock. He managed to make me cum once through my panties, and then dove under them and expertly drew three more orgasms from me in a matter of minutes. It wasn't difficult as I had wanted him for so long.

By then his cock was pressing snugly against my ass, hard as a rock. I turned around and flipped him onto his back, tossing covers and underwear until his cock was where it belonged...in my mouth. The soft light from the window let me see that he had propped his head up on pillows and was watching me work my mouth over his cock. I smiled as best I could, and then engulfed him. I felt so naughty waking up at 4am to be giving him head. I told him that my original plan was to wake him up like that in a few hours (he works Saturdays) but that I loved waking up in the middle of the night and us both realizing that we needed each other. After some good long deep sucks and massaging him right under his balls, he erupted into my mouth, and swallowed a rather large amount of cum. After that, I was able to sleep much better.

Saturday I felt the need to reorganize his kitchen while he was at work, and after dinner we watched a movie I picked out from the video store (which was amazing) and watched the first 20 minutes of a movie he picked out (much less amazing) when I decided to drag him up the stairs. I think he thought we were going to bed, but I really just wanted to be close to him to see what would happen. Bad timing or not, he was willing to put on a condom and go for it...I think he needed to be inside me as badly as I needed him there. There was no pretense, just deep hard missionary fucking that felt incredible. It was exactly what I needed.

Sugasm #124

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A glorious Tuesday evening...

I came home from work and went straight to bed. I stripped down to nothing put panties and crawled under the covers and passed out. He had instructions to find me there when he arrived.

I was awakened by a kiss and a "hey, sweetie". What a glorious way to wake up. We chatted a bit as I awoke from my slumber, but eventually I became annoyed with the conversation and pulled him on top of me. I must have been having a naughty dream or something, because I was already incredibly turned on.

I think he may have been a little surprised by my lack of clothing, but he didn't seem to mind a bit. He asked how I was, and I rubbed my hands down his back to his ass, and said "How do you think I am?" I proceeded to press my body tightly against his, grinding my pussy against his leg, holding him close, kissing his neck and telling him just how much he turns me on.

Earlier in the day, I had texted him about how much I had really wanted to suck his cock, and the feeling never left me. So when he peeled himself from my grasp long enough to stand up and start to remove his clothes, as soon as his cock was revealed, it was in my mouth. I eagerly sucked him, as I heard him suck in a breath and then moan from my unexpected efforts. "Mmm...I love when you do that." He was standing on the floor and I was leaning to the side on the bed, so he reached down and began to rub slow circles around my clit through my panties. I moaned onto his cock, as he circumvented my last piece of clothing and dove his fingers deep into me.

I moved back onto the bed a bit to allow him room to lie down. We arranged ourselves into a 69 position and kept him in my mouth the whole time. I love the smoothness of his cock as it slides in and out of my wet mouth. He licked me for a while, but eventually his lips latched onto my clit and I moaned as I came, my sounds muffled by his cock still shoved into my mouth. As I was coming down, I went to back to bobbing my head on his cock, grabbing his ass to pull him closer to me, so I could take him in deeper. He was loving it, but eventually he said he really needed to fuck me.

He flipped me on my back, pushed my knees to my chest and entered me effortlessly, as I was so wet from the artful attentions of his tongue. I usually savor the first entrance of a cock into my pussy...I like to let the idea of being full of cock slowly set in. There was no time for this...he wanted me and he wanted me RIGHT THEN. He propped himself up on his hands and began to thrust quickly and deeply. I looked down and was able to see him disappear inside of me repeatedly, which was an incredible turn on. I threw my head back and screamed...his insistent penetration felt amazing. I think he sensed I was about to cum, so he pushed into me hard, balls deep, and held himself there. I lost it...my body was writhing underneath him, rubbing my clit against his body, pulling him closer to me with my arms and legs. He shifted his hands and put his full weight on me and I exploded, screaming into his ear. I didn't have time to even catch my breath and he was already back to fucking...my pussy loved every second of it. I wouldn't let him get too far away this time though...I wanted him as close as possible to me, as deep inside of me as possible. I rocked my hips and fucked him back as best I could...we could hear the sounds of wet skin slapping together. I felt his cock just a little harder and his thrusts were just a little more determined, so I squeezed my pussy around him and whispered, "Cum for me. Cum for me now." in his ear. With a few more dips into my pussy...I was flooded with his cum. God I love that feeling.

After recovering a bit, we realized that we usually have dinner first and then fuck, which made us realize how hungry we really were. So we put ourselves back together and went out for sushi. After a delectable meal, we came back to my place and cuddled in bed a bit. I knew it was getting late and that he would have to leave soon, but my body was not done with his. Not yet.

Before he could make any exit excuses, I rolled on top of him and whispered softly, "It's been too long since you've played with my ass." There are men in this world that are all about breasts, or legs, or all kinds of things, but I've discovered M is definitely an ass man. While I'm not fond at looking at myself from behind in the mirror, he loves my behind. I can't say that I mind at all, because my ass loves the attention. I love being spanked, rimmed, and fucked there. But it's rare to find a man that is interested in the concept and will treat my ass with respect. M is one of those men.

At those words, I could feel his cock hardening below me. What I had in mind was a good tongue exploration, a bit of finger play, and then feeling his cock in my ass. But he had other plans. "My are you naughty, wanting your ass played with. Well, we'll have to see to that." He disposed of my clothes quickly, leaving me naked and him fully clothed. He motioned to a pillow, and I knew what he wanted...I placed it under my hips and laid face down on the bed, spreading my legs a bit to reveal my core to him. My pussy must have been glistening, still moist from our earlier encounter.

After a few smacks across the ass, I was left alone for a minute. I couldn't see what he was doing behind me. I learned later that he had shed his clothes and gotten into my closet to find my toys. Ahh, this was going to be a very naughty night. I have two anal toys...a long thin purple plug that feels great when deep inside, but it doesn't stay in without help. The other one was new...I had used it once in phone sex play, but M had yet to see it in action. It's a shorter but much fatter lavender plug, with a cord that extends from the base. This cord can be plugged into a battery pack with a dial that can adjust the speed of the vibration. I'd used the vibration the last time only near the time I was about to cum, and it send me over the edge and into outer space within seconds. M had heard this happen on the phone, but I could tell he wanted to witness it's effects in person.

He started with kissing and nibbling my already sensitive ass. I squirmed a bit, and even more when his tongue delved into my crack. I love how naughty that feels. He continued to probe my rosebud with his tongue as he slipped the thinner toy into my pussy. It didn't feel like much in there, but I knew the purpose was just to get it ready for my ass...and it got rather wet as my pussy was now nearly dripping. He the slowly pushed the toy into my ass. He went slow...I think he's always afraid of hurting me. I relaxed and it slid in the full length easily. He held it inside and began to toy with my clit. I loved the sensation and began to moan into the bed. He began to slide the toy in and out just a little, and then dove his fingers into my pussy. It was glorious...almost as soon as he found my g-spot, I came, flooding with juices. Anal play always gets me so worked up. He continued toying with my pussy and clit, pressing toy in deep until I came at least two more times. He then asked if I was ready for something bigger.

The base of the larger toy is wide enough that my ring barely stretches over it, so I told him that I wanted to insert it, and then he could do whatever he wanted to me. I got the lube and applied some to the toy and then fingered my asshole for a minute and somehow managed to manuever a good angle for insertion while still face down and my ass propped up in the air. I began to slowly insert the tip, taking deep breaths and trying to relax while stretching out my asshole. When it was almost in but began to hurt, I asked M to finger my clit. The pleasant distraction was enough to facilitate the entire toy slipping into my anus, and after a moment of settling, my ring closed around the receded base to hold the toy firmly in place.

I heard him sigh, and he said something along the lines of "Damn, that's beautiful...a dripping wet pussy and a naughty toy in your ass. What a dirty girl!" and then I felt a sudden sting on the most sensitive part of my ass as his other hand delved back into my now much tighter pussy. There was so much stimulation in my core that my head started to spin and I came uncontrollably.

He withdrew his fingers and let me catch my breath. I moaned that I needed to fuck him. That I craved to be penetrated in both holes simultaneously. That I wanted to be filled with cock. I think he began to move to get behind me, but I had other ideas. I wanted to ride him...NOW. As we moved to change positions, I found the battery pack for the toy in my ass and plugged it in but didn't turn it on...yet. I straddled M and kissed him deeply. After a bit of difficulty finding the right angle with the addition of a toy deep in my ass, I began to slowly lower my pussy down onto his cock. He had a rather incredulous look on his face as he felt how tight my pussy was now that I was being penetrated in both holes.

I closed my eyes and sat up tall and concentrated on the intense feeling between my legs. It's been a long time fantasy to be double penetrated, and this was the closest thing I'd ever felt. I leaned forward, squeezed myself around his shaft, rubbed my clit against his stomach and came hard, my ass spasming around the large object protruding from it. I made such loud noises. I then began a slow rise and fall rhythm on his cock, and looked down to see an approving smile. "You like my tight pussy?" I got a moan in response. I picked up the remote to the toy and turned it on ever so slowly. A gentle vibration spread quickly from the depths of my ass to my pussy to his cock. "You like that?" "Mmm, yes..."

I increased the pace of my bouncing on his cock, and increased the intensity of the vibrations as well, being careful not to let him slip out of me as I was very tight and now completely dripping wet with cum. This was nearly sensory overload for me. I began to shake with orgasm as I bounced. I'm not sure if it was my orgasm or my wetness or the vibrations that pushed M over the edge, but soon enough I could see his face contorting and his hips bucking at me and he filled me with his creamy goodness.

I collapsed on top of him, impaled on his still hard cock. I whispered to him that he had just fulfilled a fantasy of mine, and that it was glorious.