Weekend Update

Early Friday night, I had a naughty conversation with C. He's not a man of many words, but the words he does say somehow suck me in and make me want him desparately. And I quote, "I just want a two-hour or so window where we know no one is going to barge in, because I want to take my time feeling every molecule of you." It still gives me shivers. I will have him...soon.

Later Friday night was terribly disappointing. The original plan was for D to come down after work (he lives an hour or so away) and then take me to dinner, and then we'd retreat to the bedroom, as per usual, except this time I'd hoped our encounter would be a little naughtier than in the past. Instead, he fell asleep after work, and after messaging him several times, he finally woke up and didn't get to my place until just after midnight - I wasted my whole evening waiting for him.

I was tired when he got here, and he could tell, so he asked if I still wanted to do anything. I told him to convince me. His "convincing" consisted of some bad kissing, stripping of clothes and climbing on top of me. I wasn't really even in the mood, and then once he was inside me, he was at a weird angle which was putting a really uncomfortable pressure on my lower abdomen. The more he thrusted, the more it hurt, so I asked if he'd turn over so I could ride him, a request he ignored as he continued to pump away awkwardly. I think he must have mistook my uncomfortable squirming for enjoyment, but I didn't even get close to an orgasm. I had considered repeating my plea for a change in position, but I could tell he was close to cumming, so I let him finish just to get it over with. He attempted small talk, but I dozed off. He'd talked about staying all weekend...when I woke up a few hours later, he was gone, and I was glad. I texted him to say that it was a pointless experience. I haven't heard from him since.

Saturday, a bunch of people came over to our apartment to chill. The weather was beautiful, and it was the perfect time to invite over a girl, MM, that had messaged me online saying that she wanted to meet some new people, as she is new in town. I couldn't tell if she was into me (her profile said that she is also bi) or if she just thought I would be a good person to know people. We sat and dranked and talked and I couldn't get over how gorgeous she was: short, with dyed black hair and incredibly piercing eyes. Later in the evening when most people had gone to the bars, she asked if anyone ever went to the graveyard that was close by. The thought had never occured to me, so the two of us took a trip over there and even though the wind had picked up and it was chilly, we found shelter behind a large gravestone and smoked some pot and had some really good conversation. There were a few moments in which I wanted to lean over to kiss her, but I refrained, wanting to get to know her better first, as I had no idea what she wanted from me. It's funny...I've got boys totally figured out, but it's still difficult to figure out what girls want.

Sunday, I stayed in bed all day. As soon as a I woke up, I picked up the laptop and had an IM from an online friend, JL, that's currently going to school in Australia. He had a sexual question to ask, and for the next 8 or so hours, we got into an in-depth conversation about our sexual fantasies and how we'd like to see them played out - in detail. At first, it was a general conversation "Would you want your partner to do this...or this?" but it quickly turned to the two of us sharing the ideas as though it was the two of us together. His words really got to me...he came up with ideas that I never would have thought of, and I couldn't help but touch myself the entire time. I came so many times for him. We discussed his desire to be fucked by a girl wearing a strap-on, which he thought I would find weird, but it's actually been one of fantasies for a long time, to have that control over a man like that. I told him about my desire to receive a true spanking, not just as a light precursor to sex, but a punishment for all my naughtiness. He took the idea to a whole new level. We agreed that if neither of us is relationship-entangled when he comes back to the States in November, that we need to get together. He promised to make all the things we talked about and more happen. I might post some of the conversation later...it'd be too long to post the whole thing.

Monday was uneventful until about 11pm. It seems DN is serious about me being his mistress. He said that my "nonchalantness" in our real-life encounters only makes him want me as his mistress more. He wants to come over this evening for a lesson in "making Mistress cum". I think that I shall put him in his place first to see if he's really serious about this before he's granted the pleasure of being anywhere near my pussy. I think getting him on all fours for a spanking while wearing some pink panties shall suffice. The end result of this endeavor will most likely not be pretty, but how can one resist such a willing toy? If I get bored with him, then I'll release him.

Around midnight, I had to cut my conversation with DN short, as I was to be entertaining a new gentleman for the evening. This was good timing, as I was getting a little hot and bothered from reading some stories, and I love to make people jealous. Another boy I'd met online a long time ago happened to be online, so I sent him an IM. We'd traded messages over a dating site for months, always being really interested in getting together, but it never seeming to work out. I found out later that we both had been dating someone for a while, but that didn't work out for either of us. We'll call him JR.

When we started talking, he mentioned something about how I should see him naked, and I told him that I'd love to, amongst other small talk. We talked about getting together for a drink on Friday, and after all the naked talk, he thought perhaps we could skip all the formalities. I agreed, and he mused that perhaps neither of us were joking about the idea. Neither of us were, so we agreed for him to come over. After a few minutes of preparation, he was on his way. I was quite wet at the thought of fucking someone that I didn't even know his name.

When I opened the door, he looked just like his pictures, tall with short reddish hair, wearing a corduroy jacket. I led him back to my room, making small talk, and sat on my bed. He sat down next to me and kissed me, slow at first, then deeper. He pulled back and said, "Wow, you're really pretty." Which was sweet, but also a nice pick up line, not that he needed any. I told him I found him adorable, which is exactly how he said I would find him. He went back to kissing me, and then said that I was a really good kisser - I told him that I have years of practice. I leaned back on the bed, and he took off his shoes and leaned over me, kissing deeply. My hands wandered up his shirt, and his hands wandered down my body, caressing my sides down to my legs. I pulled him close and wrapped my legs around him. He moaned as he felt me press against his hardness.

I then decided that the clothes needed to come off. I helped him off with his polo, and took off my tank top. He began to caress and kiss my breasts, and he rolled a little to the side, which gave me just enough leverage to turn him over so I could be on top. I sat on top of him, gently rubbing my crotch against his, touching his body, kissing his lips and neck. I then kissed downward, on his chest toward his stomach. He sighed as I began to undo his belt and his pants. He started to make more small talk as he was taking off his pants...I think perhaps I might have been a little forward for his tastes. Once he was down to his underwear, I answered his questions between kisses of his stomach, and then I slowly slid down his underwear, revealing a stunning erection, the sight of which made me moan. He asked why I made that noise, and I told him that I liked what I saw, and that he shouldn't argue with a woman who likes his cock, as I began to lick him. I think his eyes rolled back in his head at that moment.

Between licks, I asked JR what he was in the mood for. He seemed a little thrown off by the question, wondering why he had to choose. I told him to pick a position or something he wanted to try, and that I would go back to sucking his cock until he made up his mind. I think the workings of my mouth were getting him a little too excited, so he told me to come up and kiss him some more. He decided that he wanted to be on top of me and fuck me. I rolled to my side as we began making out. His hands roamed down my body, finding my sensitive inner thighs, which made me moan into his shoulder as I was kissing it. He began to caress my pussy lips, and with an "oh, wow", he seemed to be impressed by their smoothness. I asked what he was waiting for, and he said that he didn't think I was quite ready, and he wanted to make sure that I was. I took his fingertips and delved them between my lips so he could feel my wetness. I told him I was ready, and he reached for a condom.

We didn't need much foreplay, as both of us needed to fuck. He climbed on top of me and slid into my dripping wetness easily, and we both sighed at the feeling of completeness. He was really into kissing me as we fucked, which was nice, but sometimes made it difficult to breathe. He was hitting just the right spots to make me cum, during which I ran my nails down his back and pulled him closer to me with my legs. I told him to come closer to me, to put his weight on me, that I needed him closer, and he obliged, never losing his pace inside me. He said he was going to cum, and when I said "Oh, yes!" he picked up his speed and we came together.

As we came down from our orgasms, we both laughed at the situation we were in. We chatted about all kinds of things, school and work and such. He admitted that I seemed to be more comfortable about casual sex than he was, but I told him not to worry. He vascillated between being sincere and being self-depricating, which was really charming. We laid there naked, and I just kept touching him...his shoulders, his chest, etc. I was doing it subconsciously, so when I noticed what I was doing, I stopped and apologized, as that was probably irritating. He said that he loved being touched, and that his chest and his back were especially sensitive. We chatted some more, and then he began to kiss me again, deeply, rolling onto his side giving me access to his back. He made the most wonderful sounds as I slowly and gently ran my fingers up and down his spine. He said that his ex had never quite figured out how to do that, even though they had been together for a long time. I told him I felt special for having been able to figure it out in less than an hour. I must still be really good at reading people.

After much more kissing and touching on both our parts, I felt his cock, once again hard, brush against my leg. I wrapped my hand around him and asked if he was ready for round two. He asked if I was ready and wanted to know how I wanted it. I told him to take me from behind, and he was happy to oblige. He asked if I was going to make more noise and wake up all my roommates, and I told him that this time I would be able to scream into the pillow. He was working up to a nice rhythm, getting nice and deep and hitting the spots that I like, when he pulled out too far, and on the in-stroke he missed, and nearly bent himself in two. He tried to start going again, but I could hear and feel that he had really hurt himself, so I told him he could stop if he needed to, so he did. He left the condom on, rubbing himself and trying to relieve the pain.

I sat up and told him to turn around. I spread my legs around his ass, and began to gently kiss and touch his back, especially in the sensitive places. He loved it. I told him that just because I couldn't please his front at the moment, didn't mean I couldn't please his back. I kissed up and down one side of his neck and then moved to the other side. This must have gotten him more turned on, as he told me to get back on all fours. I asked him if he was sure, and he was. He put one leg up and came into me from a higher angle, which felt really amazing. I was like an animal in heat, screaming and bucking back against him. He then put his knee down and slammed into me really hard. I came a couple times just from that. After the second time, he slipped out of me again, and I fell flat onto the matress. I could tell he was still sore, but he was not about to let me down. He put his entire weight on my back (a feeling I LOVE) and began to continue to thrust, even though he was no longer inside me. When he reached around and started to play with my clit, I bucked back at him, and he got to feel my whole body shake when I came from his touch. I don't know how he knew that I would love that.

I was barely recovering when he told me to get back up on all fours and he slammed his cock into me again, amazingly. I was a sweaty, screaming mess. I came and came for him, as he was hitting just the right spots. Did I mention that his thumb was pressing against my asshole for most of it? It felt so deliciously naughty. I had to stop to catch my breath at one point, so we paused for a bit. He asked if I wanted to change positions, and I said it was up to him. We thought that me being on top might be fun. Usually I have to explain to people that my bed makes girl-on-top difficult, but he easily figured out that he needed to thrust up in order to get maximum depth. As I bounced on his cock and started to cum, I looked down at JR's face, and he looked incredulous, as though he couldn't believe that this girl was cumming all over his cock. I grinded my pussy into him, asking if he liked it when I bounced on his cock. He said he loved it as I came again and again.

I was getting tired, and he could tell, so let me climb off, but said that he still need to cum again. I snuggled up next to him and kissed him as he began to stroke his cock. He asked me to gently bite his nipple, and I did so as I caressed his balls. I could tell he was tired as well, as he would occasionally stop his motions for about 30 seconds, and then start back up again. He was realizing it was taking a long time, and apologized, but I just wanted to help him get off, so I asked if there was anything I could do, and he said to kiss him again. I did for a while, but eventually he gave up and said he probably wasn't going to cum again. We switched sides on the bed, and when I got close to him, my fingers began to caress his hand, and he made the same noises from that as he did when I caressed his back. I then remembered a trick I learned back in middle school that drove the boys crazy. I brought his hand to my mouth, and began to kiss and lick his index finger, then lightly sucking on the tip. The transference seemed to work as he began to moan and stroke his cock again with his other hand. I sucked more and more of his finger into my mouth, and he began stroking faster. When I sucked hard all the way up his "shaft" and then pressed my tongue hard against the tip of his finger in circles, this sent him over the edge, and he came all over himself. It was incredible.

After cleaning himself up, we chatted some more, and he said that he was really enjoying his time with me. I hope that means that we'll see each other again. I wanted to exchange numbers, but didn't for some reason, but I'm thinking he'll show up again soon. Who knows, maybe we're still on for that drink.