Conversations about Crossdressing (Early Morning Version)

9:46am   L  hey there

9:46am  SA  hey sexy.  what's up?

9:47am   L  just woke up, laying in bed, naked, with a rock hard cock :)   you?

9:47am  SA  mmm...  at work, sadly.  but i woke up this morning feeling a little randy. :)

9:49am   L mmmmmm...like you needed a long hard cock in your juicy little pussy?

9:50am  SA  a big cock like yours would be lovely right now.

9:50am   L  mmmmm...i really want your mouth wrapped around it

9:50am  SA  oh ps, i love love love that pic of you that you took of your tattoo...you look so delicious...mmm...

9:51am   L  :)  glad you enjoy it

9:52am  SA  i always enjoyed you...you know that.

9:53am   L  i do...and very much likewise!

9:54am  SA yeah?  you seemed less than thrilled the last time i saw you. :/

9:54am   L  condoms dont really work for me...dont take offense :)

9:55am  SA  well, you know, a necessary evil. i now keep them in three sizes. :)

9:57am   L  nice.  i love how slutty we are :)

9:57am  SA  hehe.  well, i never know what will end up in my bed.

9:57am   L  exactly

9:58am  SA  there was a guy i slept with over the summer that reminded me of you...tall skinny big cock. very good times.

9:58am   L  mmmmmmm...sounds like the three of us would have had some fun

9:58am  SA  perhaps.  i think he was bi, now that i think of it.  he was in from out of town...my friend's boyfriend's friend from home...if that makes sense.  funny, when my friend and him broke up, he tried to sleep with me drunkenly...in front of her.  must have heard good things.

9:59am   L  mmmmm...hot.  he probably heard what a sexy little slut you are! :)

10:00am  SA  perhaps.  yeah, i chatted that guy up all night at a party and took him home with me, and then we did it again in the morning.

10:01am   L  did he have a big cock?

10:02am  SA  indeed. not quite as big as yours though. :)

10:02am   L  good girl :):)  i really want to play with your tits right now

10:05am  SA  yeah? they could use the attention. :)

10:05am   L  mmmmm...i'd love to give them what they need:  fondle them, squeeze them, suck on them, slide my cock between them

10:07am  SA  mmm...  Have you played around with any men lately?

10:11am   L  yeah, just one.

10:11am  SA  do tell.

10:11am   L  this hot drag queen...took me back to her place.  sucked each others cocks then i fucked her tight little ass

10:12am  SA  ooh, that's hot.  how did she take your big cock? :)

10:13am   L  like the dirty little slut he is :)

10:13am  SA  so naughty.

10:13am   L  very

10:14am  SA  so there's this guy that was friends with my roommates senior year (when you and i were fucking) that sent me a drunk message lst spring about how he's been fantasizing about me for years.  he ends up telling me that he wants me to fuck him with my strap on, so i do, and i come to find out later that he's got all sorts of other naughty fantasies.  [speaking of JS, of course]

10:15am   L  mmmmmmmmmmmmm

10:16am  SA  i never hooked up with him again (he was shy when not drunk) and he messaged me last night to tell me that he's been having crossdressing fantasies.  he wants me to catch him trying on my underwear and to punish him for it.

10:16am   L  fucking hot.  i love cross dressing.  my ex that we fucked together...i used to wear her panties sometimes when we fucked.

10:17am  SA  yeah? that's hot.  why did you have to go and move away? we could have had some downright dirty times. :)

10:18am   L  hah.  i know!  just the way it goes.

10:18am  SA  indeed.

10:22am   L  god damn my cock is hard talking to you

10:23am  SA  yeah? i can imagine you stroking it...what a beautiful thought.  got any other naughty fetishes i was unaware of?

10:25am   L  i love having my ass licked and played with

10:26am  SA  mmm...

10:27am   L  wanna lick? :)

10:27am  SA  i have a friend i met online that i finally got to meet in person recently (he was going to school overseas) and he wanted that done since no one he'd been with would ever entertain the thought.  it was really hot seeing how hard it made him.  [speaking of JL]

10:27am  SA  indeed i do.  (i'm getting all wet sitting here at my desk...)

10:28am   L  mmm...i want you to tongue fuck my little asshole.

10:32am  SA  ooh, that would be hott.

10:32am   L  yes it would be...tongue fuck my ass while you play with my big cock

10:34am  SA  oh yes.  and then i can trade...finger you, find that lovely spot that makes guys so hard as i take your thick cock in my mouth.  i want to watch your face, hear you moan as i work your cock...  god that makes me so wet just talking about it.  doing that would make me that much wetter...and dying to have your length deep inside me.

10:37am   L  fuck yeah.  thats so hot - finger fuck my ass while you gag on my cock.

10:38am  SA  mmm...

10:39am   L  i wish you could see how hard im stroking my cock right now

10:39am  SA  i want you to shoot that all over me, my face and my tits. i want to be covered in you...

10:40am   L  you want to be my little cum slut?

10:41am  SA  pretty please?

10:41am   L  say it ;-)

10:42am  SA  i want to be your naughty little cum slut.  do with me what you will.

10:43am   L  so naughty im stroking so hard for you 

10:45am  SA  mmm...maybe sometime i'll try to take you in my ass...see how far you can stretch me before i can't take it anymore.  would you like to have my tight ass wrapped around you?  i think it would be so hot to ride you with you deep in my ass. you could rub my clit and i would cum so hard for you.

10:47am   L  mmmmm fuck yeah. lube up your tight little asshole and slide my cock in nice and deep.  finger fuck your cunt and make you squirt all over my body

10:47am  SA  oh, fuck yes.  i would love being so full of you.  god i need to cum.  my panties are ruined for the rest of the day. ;)

10:48am   L  ooh,  i want to wear them.

10:49am  SA  you can put them on and then clean up this mess you made between my legs with your tongue.

10:49am   L  oh yeah, i want to drink your pussy juice

10:52am  SA oh yes.  get my pussy nice and ready for your cock. i want to get on all fours for you...you can pound me from behind...pull my hair as you slip your thumb in my tight ass.  i want to see how deep you can get inside me.

10:53am   L  sooooo fucking hot

10:54am  SA  god i need your cock right now.

10:55am   L  and i need your cunt

10:57am   L  and i need to get ultra, nasty, dirty kinky with you

10:57am  SA  yes please!

10:57am   L  i mean really kinky...

10:57am  SA  such as?

10:57am   L  laying down in your shower so you can piss on me

10:57am  SA  ooh, naughty boy.

10:58am   L  very naughty.  im a total slut :)

10:58am  SA  and that's what i love about you.  cum for me yet? ;)

11:03am   L  not yet.  fantasizing about you standing over me in the shower

11:03am  SA  mmm, holding on, eh?  yeah? you want me to let go all over your face?

11:04am   L  yes, i want to taste it.

11:05am  SA so naughty.  you can lick me clean when i'm through. :)

11:06am   L  mmm...nasty.  i love it

11:06am  SA  i bet that would make your cock throb.

11:06am   L  it would...it is.

11:07am  SA  tsk tsk

11:07am   L  i want you to make me your filthy whore

11:07am  SA  oh i can do that.  do you like to be spanked?

11:08am   L  yes

11:08am  SA  good...cause i have a riding crop that hasn't gotten much use.

11:08am   L  yea, make me your bitch

11:09am  SA  i can dress you in my panties and then redden your ass with my hand first and then the crop, telling you all the while what a dirty nasty slut you are.

11:10am  SA  then i can pull the panties to the side and slide the handle of the crop in your tight little ass while i rake my nails down your back.  i would tell you to be loud...to moan and tell me what it feels like and how naughty you are.

11:12am   L  oh my god thats hot.  i want you to totally dress me...panties, thigh highs, little skirt

11:12am  SA  turn you into a dirty little girl?

11:12am   L yes

11:13am  SA   take you over my knee and spank you like you deserve?

11:13am   L  yes... oh god yes.   spank me for being such a filthy slut

11:15am  SA  pull your hair, make you tell me all of the naughty things you've done that so i can decide on the proper punishment for each of them.

11:15am   L  yes!

11:15am  SA  i think the proper way to handle your naughty time with that drag queen would be for you to be fucked the way that she was.   bend you over the nearest object and hike up your skirt...rip your panties off and slide the large end of my double ended strap on deep inside of you.  see if you can take it like she did.  fuck your tight ass until i cum...

11:18am   L  fuck yeah...fuck me rough.  make it hurt.  abuse me.

11:19am  SA  oh yes.   nice and deep and hard, just the way you need it.

11:21am   L  mmmmmmm.  oh god, so hot.  i want people watching you rape me.

11:22am  SA  yeah?   you want boys or girls watching?  i think it should be boys so they can stroke their cocks while watching me fuck you silly.  i want you blindfolded. i don't want you to see them, i just want you to feel their presence, to hear them. to have to guess how many there are and what they are thinking.  i want them to take turns in front of you, making you pleasure them with your mouth as you take my cock deep in your ass.

11:25am   L  oh my fucking god thats hot

11:26am  SA  after they've each had a turn, i want to flip you over and pull you to the edge of the bed and let them each have 10 strokes in your tight little ass, not letting them cum inside you.  you have to get used to the various shapes and sizes of cock coming at you.

11:28am  SA  then i want them to stand around your face and finish themselves off on you.  i want you to taste the combination of their juices.  then, and only then, can you touch yourself and make yourself cum...while i shove and even larger toy in your ass...even larger than any of the cocks you've just had.

11:29am   L  that sounds amazing.  i just came so hard.

11:29am  SA  mmm, yes.   you like group sex fantasies where you're the center of attention?  did you make a mess? :)

11:33am   L  i just love group sex

11:33am  SA  haha me too.

11:33am   L  and yes i did.  all over my tummy.

11:33am  SA  mmm...i wish i were there to lick it off

11:35am   L  me too :)  god that was hot.  i am going to go clean up and take a shower.  i'll talk to you soon.

11:37am  SA  hehe, ok.  peace.

A few thoughts...

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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 tongue...it 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!

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.