5 hours of fun - Part 1

I dressed up for him - I haven't done that for anyone in years. His specific request was for stockings and heels so I made sure to have them, along with a bra that I was spilling out of, a waist cincher and black panties with red cherries on them and a floor length red robe tied just under my tits.

I was nervous waiting for him, not exactly sure what I gotten myself into. I was afraid of disappointing him, as I felt I had the last time we were together. I had waited for this for so long, I really didn't want to mess it up.

He said he was impressed with what I came up with, despite my telling him I'm not one much for lingerie. I was in awe that he was in my house, in my bedroom, and could only imagine the fun we were about to have. We kissed, then I sat down on the bed to show off the stockings he requested. He seemed to enjoy them.

He was really there to be fucked, so just the robe came off of me but we got him completely naked. I relished the sight of him as he laid down on my bed sideways, spread eagle. I never in a million years would have thought this would happen, him eager and willing to let me have my way with his ass.

I got down on my knees, and placed a pillow under him so he was at the proper angle. My nails were too long to warrant fingering him so I started with beads, nothing too large, to serve as a warm-up.

We talked through it, to make sure he was ready for the next bead and that I wasn't hurting him. I had a whole host of toys and wanted every last one to make it inside of him.

I loved watching his face, the pain that evolved into pleasure as each bead disappeared into his willing ass. I slid his cock into my mouth once most of them were in, and his eyes nearly rolled back into his
head. I enjoyed giving him this unique pleasure.

He became a bit uncomfortable once they were all in, so I slowly withdrew them. Up next was a vibrating plug, one of my favorites. It was too large to get all the way in at first but he definitely enjoyed the vibrating sensations. I wish I could have recorded just the looks on his face. "Let's make that the end game, I could totally cum just from that."

From there we moved on to a dildo...while small in diameter it has a interesting curve to it. I slid it in as far as I believed that special spot to be and then rolled it in a circular motion.

At this point, he was eager to see me with a cock of my own. We chose the double ended one, and struggled a bit with the straps as it had been a while since I had last used it. Of his own accord, he got own on his knees and sucked my big purple cock. I gently guided his head as he worked it, enjoying the gentle sensations inside of me from the other end. "I've seen this done in porn and it never really did anything for me, but in person, it's really hot...mmm..."

"Let's try that last toy and if it slides in easily than I'll let you fuck me with this." Considering how unsuccessful my last attempt to fuck a boy in the ass was, I wasn't going to hold my breath. But the opportunity to take him like that, it was almost too much to imagine.

I got out the next toy, my favorite one. "My friend calls this my David Bowie dildo because it's silver and sparkly." This toy has a slight curve, but mainly just gets slightly larger as you move toward the base. I used lots of lube this time, wanting to make sure I didn't hurt him. I slid it in ever so slowly...he barely moved at all and so I just kept going. He asked at one point why I hadn't put it in very far and I told him it was about 2/3 in...he reached down to feel it because he didn't believe me. Holding the toy inside him, I stood up and leaned over to kiss him. I began to fuck him gently as I kissed down his body. "You're ready for my cock, aren't you?" He nodded.

I had invested in some under the bed restraints months prior to this occasion, but had never gotten the opportunity to use them. I was glad I had saved them for him. I really thought he would use them on me but he turned around on the bed and actually started to put himself in them. I tightened the straps, and leaned back. This is something I never  expected to see - KH in my bed at all was shocking enough. But in restraints, it was too delicious.

I grabbed the lube, pushed his knees to his chest, and prepared for entry. It was difficult to get the correct angle at first, but it was so worth it. I loved feeling the pressure on my clit and inside me as I pressed into him. The restraints weren't working as well as either of us had hoped as they are designed to have all four extremities in them at once, so I pinned his hands over his head and kept on fucking. I kept watching his face to catch any glimmer of him being uncomfortable but I didn't see anything but pleasure. My cunt was dripping at this point,the entire thing was so intense.

I soon realized that being the one doing the fucking was exhausting! I sat down for a moment, and then had an idea. I pushed my cock down and attempted the lotus position. It seemed to work at first, but after a while I could tell it wasn't the proper angle for him. I had every intention of flipping him over and fucking him from behind but he had other ideas.

"Is there way to leave that strapped on but pull it out so you can sit on my face?" He was totally topping from the bottom, but how I could resist his tongue exploring my cunt? I'm always a little nervous about sitting on anyone's face, I don't want to smother anyone...but sometimes I think this is the point. The strap on got in the way so I took it off and let him have his way with my cunt. I must have covered his face in my cum I was so wet.

After I came we took a break for a bit. I thought he would want me to fuck him some more, but he had much more intense ideas. I had mentioned something earlier in the evening about needing a spanking.  Somehow, I had forgotten that this wasn't going to be an open hand spanking where I get to touch myself and cum whenever I want to. I was about to get the most intense beating of my life.

The tables have turned...

He all but begged to come over back in January.  A boy I chatted with a bit on Fet that didn't go very far had randomly reappeared wanting to fuck. But not just fuck, to dominate me, something I'd been craving for a long time.  While I've had men that have taken control, those experiences didn't contain the "yes sir" and the power exchange that I'd been dying to experience.  This gentleman, although 6 years my junior, seemed to really know what he was doing.  His various photos and related commentary seemed to show that others were willing to submit to him, and so was I.  We'll call him KH.

He took a different angle than I had expected, sitting down in my living room and asking me about my day.  This didn't last long however, I was not about to let it.  I needed him and whatever he was willing to offer.  He asked me my safe word, and soon as it left my lips I was instantly on the bed via his hand against my throat.  He was not playing games - he meant business.

He left bite marks on my chest, I cried when he teased me with the crop, scared of him hitting my pussy.  I didn't expect to cry and felt embarrassed, but he seemed to eat it up.  It was a delicious sense of release.  I got down on my knees and sucked his cock.  Before I knew it, I was on all fours getting my ass railed without any warm up, being told I couldn't cum until he told me to.  It hurt, but I relished the pain, the attention, the knowledge that he was using me for his pleasure.  It wasn't about me, it was about him, and I loved being his toy.

The next day I was on a flight to LA and could think of very little but him and the experience for the rest of the trip.  I tried to explain to him in text how and why the experience was so significant to me, but he didn't seem to understand or care.  It was frustrating, but I also understood that he has just gotten out of an intense relationship and I was just a distraction, among many other girls. I just couldn't get him off my mind...I wanted more.

KH had posted a wish list online, mostly small toys.  He had told me I was too loud when we played, so I picked the ball gag.  I eventually told him who sent him the gift, and when I ran into him in the bar, he asked why I sent it to him.  I told him that although I wasn't sure how I felt about the idea of being gagged, but I wanted to please him and thought that he could use it on me the next time we played.  But that "next time" remained elusive.

The internet eventually told me he was in an exclusive relationship.  Despite his ability to dominate many girls at once, I could tell that he is much more comfortable being with only one woman, and perhaps bringing in other play partners on occasion.  Despite my desires, I was happy for him, and had all but written off the idea of seeing him in my bed ever again.

Still, he had this effect on me that I couldn't shake.  He was my main source of material for masturbation fodder, and yet when I saw him in public I couldn't help but be bitter that we hadn't been with each other again.  Bitter and wet.

One day he posted that he had lost all his contacts and wanted people's numbers.  Not saying who I was, I texted him and expressed an interest in submitting to him again AND his woman.  He wasn't really sold on the idea, most likely because he didn't know who I was but also because he alluded his woman being quite busy and not having much time for him, so I could understand that for the time that he was with her, he'd want her to himself.

A few months later I was with a group of friends at a local bar, one of which was an old friend that had moved away but was visiting for the weekend.  KH started talking to this friend and I was drunk and probably glaring at him, so he tells my friend "We fucked and now she hates me, so I should probably go."  Forgetting about our "anonymous" conversation, I texted him to say that I didn't hate him.  I wondered if his mind would change about my proposition now that the source had been identified, but I wasn't about to ask.

A little later that night I go outside and find one of my best friends engaging in a literally 10-15 minute long hug with him.  People do strange things when drunk, but I was just standing there feeling awkward and jealous but unable to walk away.  I still wanted him - I couldn't help it.  I hated that he had such an effect on me, especially when I seemed to have virtually no effect on him.  I was just another number.  But on some level that was also hot, to know I was included on such a list, albeit for an extremely brief experience.

I did my best to put him out of my mind.  I started fucking a few new people, nothing kinky but still satisfactory.  I was willing to wait until my upcoming move to a much larger city to try and seek out any kinky people.  However, there was another boy on Fet that was looking to be used by a girl with a strap on.  I love giving people their first experience so I agreed to let him come visit.

That same evening, before this new boy came to visit, I noticed that KH had started a kinky tumblr blog which posted updates to twitter.  Of course this was too tempting to resist looking at.  One of the posts showed a .gif of a man being pegged with a big black strap on and his caption was "I need some of this, today, now." He had mentioned to me previously that he can "take it in the ass like a champ" but I didn't think this was ever something he would crave, it just seemed against his dominant nature. Still, I sent him a private message saying "Oh I'll most likely be doing that later tonight".

I had completely forgotten I had sent this until a week later when he sent a message back asking me what I referencing and that I should I text instead.  I couldn't pass up the interaction even though I'd been trying to avoid him.

As soon as he found out that I am willing to peg, he said that he may have to visit me because it had been far too long since he had been properly fucked.  My pussy immediately became wet at the mere mention of the idea that he would offer his ass to me.  He explained that his relationship had become open and that he could play with whomever he wished.  After craving him for over six months since the first time we played, I couldn't help but be amused...now I had something that HE wanted.  A flip of the power exchange that I wasn't really expecting but I liked it more than I thought I would.  Still, when he mentioned that he might go "full sub" I was bit sad.  I relished the idea of giving him what he was craving but also feared that I would respect his dominance less if I saw him in such a state. Still, I was willing to try, and what actually happened was much more fulfilling than I ever could have anticipated.

Office Sex, etc.

I've only worked here 6 years, and finally was able to hook up in my office.  It wasn't long after 5pm but it was on a day my boss wasn't in since she usually worked late.  I hadn't seen C in forever, he had a lot of personal drama going on and I wasn't about to get involved.  But one afternoon he began texting me, desperate to see me.  I wasn't quite sure when the cleaning staff came to the office, but was willing to take a chance.

I shut the door behind me and turned around.  His mouth attacked me, his large lips enveloping mine, hungry and filled with need.  I can feel his erection pressing against me already.  He apologizes in advance for not keeping up with his shaving (he usually keeps his member completely smooth) but I didn't mind, I liked his cock for it's size, not for the absence of hair.  He undoes my pants and slides his hand underneath my panties and is greeted with a wet pussy.  I remembered the times we had been together before and wanted it all again, except this time, in a much more taboo locale.  The mere thought had me dripping.

His fingers expertly bring me to a shuddering orgasm - my knees buckle and I nearly collapse in his arms.  I push him back in my chair and get on my knees.  I needed his cock in my mouth and I needed it immediately.  I took him in my mouth as far as I could.  He reiterated previous notions of him not really enjoying blowjobs unless I was the one performing them.  I smiled around his cock and quickened my pace.  I looked up and watched his eyes nearly roll back in his head.  He eventually stops me.  I thought I had done something wrong, but he just really needed to be inside me.

My desk had too many things on it to be bent over it properly so we chose the floor.  I laid on my back and relished the full feeling in my cunt when his huge cock entered me to the hilt.  I needed to be fucked hard and fast, no playing.  He tried to slow down but I wouldn't let him, bucking my hips up from floor needing more and more of him inside me.  I was able to reach one small orgasm before he flooded me with his cum.  Needless to say I was disappointed, this was not the fucking I had envisioned!  He tried to finger me again after that but the moment was lost.  He claimed that my blowjob had gotten him too excited.  For someone older than I, I thought he would be able to control his orgasms but apparently not.  I mean, I guess it was nice to know that I get him so excited but still.

Later that evening, I ended up seeing SM and sleeping in his bed.  I hadn't yet showered but it didn't matter, we didn't do anything sexual, we just cuddled.  When I woke up in the morning, the sunlight pouring over his body was almost too much handle, he was so beautiful - an image forever burned into my memory. I didn't want to leave but I had to.

That night, I met up with my RW and our mutual friends.  Again, everyone passed out and we stayed up talking forever.  Out of nowhere, he grabs my hand and puts in on his junk, then leans forward to kiss me and then somehow in all one motion pushes my head down. "No one ever taught you proper head etiquette, eh? All you have to do is ask!"  I remove his pants and take his cock into my mouth.  He's awfully quiet so I'm not really sure if he's into what I'm doing but then I realize he probably doesn't want to wake anyone up. Eventually he leads me to his room and bends me over and fucks me from behind.  This is definitely fucking for the sake of fucking - no passion, no romance, just sex.  I completely respect it.  While the details aren't all that sexy, I still come a few times and don't regret the experience.  I wonder though if his sister (my friend) could hear since her room was right next door. 

Where should we go?

A friend's brother and another girl came to town late one Friday night. I thought they were dating, but on Saturday I learned that they weren't. I wasn't immediately attracted to the kid but the more he talked the more I became interested. Still, strange ground to try and discover when he's related to a pretty good friend.

A group of us were hanging out, and one by one everyone crashed but the two of us. We went outside to talk so he could smoke and our voices wouldn't bother anyone. We talked about everything, but as most conversations go, eventually it turned to relationships and sex.  I gave him my standard diatribe on how I eschew the ideals of the traditional relationship, which I have realized is basically the intellectual version of saying I'm DTF.

We were sitting rather close, and I can't remember who kissed who first but quickly we realized we needed to fuck but weren't quite sure where to go.  My place was a bit of a walk, the back of our friend's truck was considered but I feared it would be too noisy.  He grabbed my hand and led me around the back of the apartment building, to the side that faced the woods.  I knew that our friend's windows may be open and that they could hear, so I tried to be quiet as I got down on my knees to take him in my mouth.  I didn't get much chance to pleasure him this way as he pulled me back up, kissed me roughly and yanked off my pants.

I was a Girl Scout once, so I was prepared...I had a condom in my pocket that I handed him.  He put it on quickly, then pressed me face first into the brick and came at me from behind.  I nearly bloodied my lip as I bit it to keep from screaming out loud as he entered me forcefully.  It was exactly what I needed.

We are about the same height, so for him to penetrate me fully, we would need a different angle.  I pushed back into him and leaned over farther, grabbing my calves and pushing my ass out.  I was just the right way to get him to hit the spots I needed to cum hard.  He pounded me and came rather quickly but I was still able to cum with him.

We redressed and went back to the porch, and not long after the friend he had come to town with woke up and started talking to us, even asking him why his fly was down.  I was pretty sure she had a crush on him so I found the entire situation hilarious because I was pretty sure there was no way she could have known that we just went at it.  Also, I never told my friend that I had fucked her brother.  She probably wouldn't have cared but I'm pretty sure he would have been weird about it, and why would I want to create an awkward, unnecessary situation?

Memorial Day Weekend

After hours with friends at SM's place. I ask if I should stay or go, he says stay. We go to bed soon after that. He strips naked before going to bed but I only take off my pants. We immediately embrace. He says "if I'm teasing you too much you don't have to do this." It had been a few weeks since I had been here...I wasn't really thinking about sex, I just wanted a hug. "This is all I've wanted to do for two weeks, just hold you." He hugs me tighter. "Sex...is just icing." He pulls back a bit, looks me in the eye, and then kisses me deeply. "But sometimes it's just nice to do that." "Indeed." We realize that me still wearing a shirt is awkward, so it's removed. We continue to kiss and eventually I feel his fingers slide under my panties and inside of me, feeling my wetness.  He finds the right spot inside and sends me over the edge.  I'm compelled to keep relatively quiet and instead grab him tightly.  He kisses me as I come down from ecstasy. I explain that there are 2 different types of girls, those that build up to one orgasm that may or may not come, and girls like me that can keep on orgasming forever if allowed.  I think this was my subtle hint that I could have cum a few more times but I could tell that he was tired. We change our embrace naturally and settle in for sleep.  I commented on how with some people I toss and turn but I like that he and I fit together. We pass out and the next morning I give him a back rub and we get lunch together.

*****

As I was hanging out with friends, SM calls says he's having after hours.  I meet new some new people, and we stand on porch and chat for a long time. They leave, then SM and I listen to music. The Pixies, then the Mountain Goats, then Do Make Say Think. I love singing along to the Mountain Goats with him, it's a moment. In the middle, he asks "Why do I feel uncomfortable right now?" "Are you cold?" He wasn't wearing a shirt and we had just been outside to smoke. Shakes his head. "I shouldn't feel uncomfortable around you..." I say that I'm sorry I make him feel that way, it's not my intention. "And once again I'm hammered and you're not." "I'm used to it, don't worry about it." He says he needs to go to bed soon as it was almost 5am.

He again strips naked for sleep, I leave my panties and tshirt on. We embrace, his leg between mine, my leg over his hip. "I feel like all I do is tease you." This was sort of true but I never believed it to be intentional. "Nah, what makes you say that?" "Because i'm always too drunk to do anything". "I don't expect anything when I come over here. I just like to spend time with you." This was the truth.  He grabs me and holds me so tight.  I was happy to be on the same page with him, and expected to fall asleep in that exact position.

He goes in for the most intense kiss out of nowhere, and I'm taken aback for a second and apparently don't seem as into it as he would like. "Don't hold back." In between attacking him with kisses, I explain: "I'm not...I just never know what you want...you're really hard to read...you said you wanted to go to bed...so I believed you". I was practically on top of him at this point. He starts scratching my back intently, his thigh wedged between my legs, his mouth on my throat. I pull away long enough to remove my shirt. Simultaneously he pulls off my panties. I pull him on top of me. He sort of missed when he came in for the kiss, and I adjust a little under him and admit "You may or may not have just licked my eyeball. That was pretty funny." We both laugh hysterically and he rolls off me for a moment.  He mentions "I'm so glad we can laugh about these things."  "I think we have fun, right?" I ask. "Hell yeah we do." "And that's what it's about."

Somehow we went from laughing to him pinning my hands above my head, kissing down my body, until his fingers began to explore me inside.  I was not quite wet and it hurt a little. I waited to see if my body would adjust but it didn't, so I advised "not so deep".  He listened, and pulled his fingers back a bit and found a spot that hadn't been hit in a long while, pressing deeply downwards. I begin having explosive, convulsive orgasms - if his fingers weren't inside me, I could probably be mistaken for having a seizure. Somehow he ended up on my side of the bed, and I was perpendicular to him. "I have you figured out. I stay shallow and then press when you squeeze my fingers." I had no idea there was a method to the madness but I loved every second.  I think my vagina squeezing him was involuntary which made it that more interesting.  He came up and let me taste myself on his lips. I get very comfortable after so many orgasms and him by my side.  After a moment I move back to where we had started - we had to find his pillow, it had somehow migrated in the craziness of my orgasms.

Coming down from my orgasm high, I sigh, "You're wonderful." His response?  "I'm a fucking asshole."  There is a really long pause. "I'm a fucking asshole who happens to like you." I smile. "I like you too."  I fell asleep happy.