Monday, May 12, 2008

Anal Attentions

This week, I have had three men approach me with the fantasy of me fucking them in the ass. I was able to make this fantasy come true for two of the three - the third being located halfway around the world was the only obstacle to having the fantasy of all three men come true.

After much thought on the subject, I have decided to take on DN as My slave. He refers to Me as Mistress, he does not cum unless I say so, and I'm having him write his own blog about his experiences. Being such a shy virgin, I allowed him to keep his journal private, but I may cross-post here as I see fit. Although I am not attracted to slave in a conventional sense, I am attracted to his devotion and the idea that I am the first person ever to have any sort of sexual contact with him. I enjoy playing teacher sometimes, so how could I resist such a willing student?

I invited slave over to play Saturday afternoon. slave was to arrive freshly showered and with a gift for Mistress - something with meaning to slave. he has spent time in Japan, so he gave Me a coin, which is a symbol of good luck. When I had slave recount his experiences in his journal, he said that he had practiced describing the gift to Me, so that he would not stumble over his words and be unpleasing to Mistress upon arrival. I told slave to undress, and to come sit on the bed next to Me. slave was so nervous he was nearly shaking. I was very kind to slave, touching his face, reminding him that he has many lessons to learn from Mistress, and that he should remember his safe word.

I began by touching him gently...his arms, legs, and back. he shuddered under each touch, making indescribable noises. he had never had anyone touch him in this way. he arched his back as I ran My nails down his spine. slave's cock began to drip precum, so I took a drop of it on My finger and made him taste it. "Do you like the taste of yourself?" "Yes, Mistress."

I pushed slave back onto the bed, and knelt before him to inspect his cock. My fingertips traced circles on his inner thighs and pelvis, which turned into scratching - the whole time slave could not keep in his noises and subtle movements. Mistress was gracious to slave to allow him these reactions, but may not do so in the future. slave's cock nearly became a slow running faucet, and in order to save My sheets, I began to spread his drippings on his inner thigh, but still not touching his cock.

I then had slave get on all fours on the bed to prepare him for his anal training. slave wishes for Mistress to fuck his ass one day, but clearly slave was not ready for such treatment. he needs to be trained to be able to receive My cock. Once he was on all fours, I pushed his shoulders down to the mattress, in order to get his ass up high enough for what I was planning. slave said later that he loved being pushed down in this way. slave is learning that he is better off under My control.

slave had made a few transgressions during the week, mostly touching himself without Mistress' approval. However, he did not cum, and was thinking of Mistress when doing so, so I only gave him a few spankings and scratched My nails down his back, ass, and thighs. I also bit his ass cheeks, which he had an intense reaction to, and played with his balls which really made him shudder. I got out the lube and played with his hole using My fingers...he was so tight. I then got out a small butt plug (about 5 inches long and about an inch wide) and lubed it and then began working it into his ass. I made slave tell Me how it felt, and he said the mixture of pleasure and pain was indescribable, and that he was grateful to Mistress for Her attentions to his ass. I was able to work the toy all the way inside him, and decided that slave's first penetration was a memorable event, so I took this picture:

I slowly worked the toy in his ass while playing with his balls, and he loved every second of it.

After I removed the toy from his ass, I told him to get up and sit on the floor cross legged. I asked slave if he wanted to see what fucking slave in the ass had done to Mistress. he very much wanted to see. I took off My pants, sat down on the bed and spread My legs so that his face was about 3 feet from My cunt. I fingered My clit, spreading My juices around, and slave's eyes got wide. I got out My own toy, laid down on the bed and began fucking Myself with it. slave very much wanted to serve Mistress orally in this moment, but I was too far gone in My needing to cum that I really didn't care. I fucked Myself harder, enjoying the audience, and came all over My dildo. I then held it up for slave to clean with his tongue, and asked if slave enjoyed watching Mistress cum. slave thanked Mistress for the opportunity to watch Mistress orgasm.

I then had him lie upside down in My bed, and climbed on top of him in a 69 position. It was now time for his oral training. I straddled his head and got within a few inches of his face, and told him to breathe in Mistress' scent. I then instructed him to explore Me with his tongue. slave was rather good for never having been anywhere near a pussy before, let alone one that was upside down. Eventually, slave found My clit and I came in his mouth, while grabbing onto his thighs. I never once touched his cock during this time.

I had kept My shirt on this entire time, so I took it off and straddled slave right side up. I smothered him with My tits and then gave him permission to touch them. his touches were extra light, and he rolled them around in circles. I began to rub My clit against his stomach, covering him in My juices. I told slave that he was to wear My juices on him all day and all night, and that he was to blog about his experiences with Mistress. I then came again, all over his stomach.

I rolled off of him, and asked slave if he would like to cum. he asked politely for Mistress' permission to cum, so I allowed him to touch himself. slave complained that he was in an awkward position as he is used to sitting in a chair. I told him to cum anyway. he tried, but was unable to, but I believe it had more to do with being nervous than the position that he was in. I told him to sit up and lean against the wall, and I did so as well, but on the wall perpendicular, as My bed is in the corner of the room.

I sat back and smoked a bowl and chatted with slave, and had slave massage My feet. I then played with slaves balls with My feet. slave said he felt very comfortable being naked with Mistress, but normally this would terrify him. I asked if slave still wanted to cum, and he did, so I let him touch himself again, but I was growing tired. slave was still experiencing performance issues even when sitting up, so I dismissed him. I told him to get dressed because Mistress was tired. He whined slightly, but I gave him a look that stopped that. he then thanked Mistress for the opportunity to serve Me, put on his clothes, and left.

The entire experience was very arousing, so I got myself off once more before taking a nap. I've always known that I'm almost more turned on by ideas than by actions, which is why I've always preferred erotica to porn. So it was interesting to see how turned on I got by interacting with someone I'm not inherently attracted to, all because the nature of our interactions put me in control. Why didn't I do this before?


Later that evening, I had a social gathering at my place, and a few of us stayed up until quite late. I was looking at some pictures I had posted online, and noticed that someone had sent me a message. It was a friend of a girl that lived near me nearly three years ago. I'd nearly forgotten this boy existed, as we had never really talked and had just drank together in a group setting a few times. We'll call him JS.

His message was missing a few words, which laid clues to his level of intoxication. The gist of the message was that he wanted me. I happened to catch the message just as he had written it, so I responded with "Oh really?" and he said he's looked and my pictures and thought about me. Now, all the pictures I have posted on this particular site are pretty tame, save for a few low-cut shirts I've worn. So this was screaming "I love your huge tits and like to jerk off looking at them." This would probably be a turn off to a lot of girls, but not me.

I found his screen name and messaged him more directly. He wasn't sure I remembered him, but I did, and proved it by digging up an old picture of him shirtless. As I probed him with questions, I think he was starting to regret telling me about his long held desire for me. But then I made a deal with him. He needed to tell me about some of his fantasies, and in exchange I was to see what I could do about making some of them come true. He thought this would be alright as long as I shared some of my fantasies with him. I agreed, and I think he was just intoxicated enough come right out with the idea that he wanted a girl to be aggressive with his ass.

I asked if he just meant that I should finger him, or fuck him with a strap-on. He couldn't believe that I said that because that was his ultimate fantasy, but he wasn't sure if he'd be able to take it right away. I told him I could work up to it. At this point he really wanted to come over, but it was around 4:30am. I told him that I needed to get some sleep and that he should come over the next day, but after further discussion and his expressed desire to eat my pussy, we were both so riled up that we needed to make this fantasy come true. He called a cab and arrived at my place around 6am.

When he walked in I was lying down as I was pretty tired, but seeing his smiling face perked me right up. He was just as gorgeous as I remembered him. He was really nervous, but once we got kissing and I pulled him on top of me, he relaxed a little. I rolled on top of him and started taking off his clothes. When I began to pull off his boxers, he got really shy and covered his cock with his hand and asked if we could turn the lights off. This really annoyed me, as I like to see what the hell I'm doing, especially since I was planning to penetrate his ass in a little while. I succumbed and switched off the light, and went back to admiring his cock, taking it into my mouth.

He seemed uncomfortable by this action, as he had discussed that he wanted me to be in control and wanted to please me. (It seems that I am flypaper for submissives.) He wanted to go down on me, so I happily switched places with him and spread my legs. He was more talented with his tongue than I expected, especially since he was only using his tongue and not the rest of his mouth. I came for him several times, especially when he began to finger me. I remember thinking "This is the life...having boys come to me to eat my pussy whenever I want" as I came again. I became a little sensitive, so I sat him up and kissed him, tasting myself on his was delicious.

I asked him if he was ready to be fucked, and he said he was. I got him on all fours, but he had his ass too close to the bed so I had to reposition him to get him at the right angle. I got out the lube and began to slowly finger him, finding his spot and massaging it, which made him moan. He loved it. I then got out my toy (the same one used on slave, cleaned, of course), and lubed it and slid it inside slowly. He soon began pushing back on the toy...he really wanted to be fucked. I asked him how he liked it, and he said that he wanted me to be on top of him, so I bent over and laid my breasts on his back and thrusted my hips into him as I continued to use my hand to fuck him with the toy.

It was seriously one of the hottest things ever, this beautiful, tan, smooth skinned boy that I have bent over on my bed, fucking his ass, and him bucking back against me, moaning and loving every second. As much as I enjoyed playing with slave, this was much more enjoyable because of the give-and-take. After a while he said he wanted to fuck me, to which I told him I wanted him to fuck me from behind. I figured we might as well do a true switch, and besides, I love getting pounded from behind.

We got into position, and I thought I felt the head of his cock against me, but then he decided he wanted to finger me some more. His hands were quite dexterous and he fingered my clit and found my spot inside and had me gushing all over his hand. I found it really hot as I am not usually fingered while in that position. He had me panting and begging for him to fuck me. He just kept fingering me, but after I asked enough times, he said "It's been a long night". I understood, so I had him lie next to me as I recovered from my orgasms. He held me close, and said that he was a cuddler and he liked being near me. How could I resist his strong arms around me? I nearly melted.

We began to kiss, and his hand gently rubbed my clit and our kissing became more passionate as he brought me to yet another orgasm. I felt his cock brush against my leg - apparently our kissing got him hard again. We had talked about how he would like it if I rode his cock so my tits were swinging in his face and he loved the idea so that's exactly what I did. I climbed on top of him, and guided his cock inside me. The sensation of being penetrated was completely worth the wait. I rode his cock desperately, and he grabbed my tits and when I leaned forward, he began to suck on a nipple. I came on his cock several times, pushing on his chest, screaming, and grinding my clit against him. He loved it, and eventually said that he was near cumming as well, so I increased my pace (if that were possible) and we came again together. It was exactly what both of us needed.

He texted me the next day, saying that thinking of me made him get off really quickly, and that he couldn't wait for me to fuck his ass again. We messaged back and forth until I was so hot and bothered that I had to get myself off before passing out again. I like it when boys come at me from all directions.

I wonder what this week will entail...slave and JS could easily keep me busy, but I'm considering calling A to see why he's AWOL yet again, and who knows what will happen with C - last weekend he drunkenly called at 3am wanting me to come to his office to fuck him. I declined as I was dead asleep when he called, and he was slurring his words enough to make it not a good idea. I can't wait to talk to JL about all of this. He'll be envious. :) Off to more adventures!

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