As per usual I had several messages in my OkCupid message inbox.  At least one was probably written by someone with the reading comprehension of a toddler, at least one was probably trying to set up a meeting, and one was from a guy who claimed he didn’t message many women.

He claimed not only in his message to me that he didn’t message many women, and so my profile must have really been special to make him do so, but the text in his profile indicated that it wasn’t his habit to message ladies because he was a busy guy.  He was busy traveling to England, where he grew up so he had a British accent, and Italy, from where his mother’s family hailed so he spoke Italian, going to medical school, and fixing up the house he just bought in Lincoln Park.  Oh, and he loved to cook – Italian, of course, since that was the food his mama fed him.  Did I mention that he was also really cute, 6’6″ tall, and in really good shape?

I suppose I was supposed to feel special because he did take the time and effort to send me a message.  I’m not sure how special I felt, but I did respond by giving him my YIM user name so we could chat some time.  I didn’t bother telling him when I’d be online and changing my YIM status from “invisible” to “available” however, just told him that if he felt like chatting to hit me up and I might respond.

I believe it was a Saturday afternoon that I saw that he has instant messaged me.  I responded.  The conversation began innocently enough and then he asked what so many guys have asked before, “I hope I’m not being to forward, but can I ask you a question?”

That is always followed by a question of the sexual nature.  Always.  He asked if I had ever been with more than one guy at a time.  Yes.  He asked if I had done DP.  Yes.  He asked if I had done DP with “larger” guys.

Here is where I had to have him clarify.  “Larger” could mean a lot, depending on who’s defining it.  Larger is in the hand of the beholder.  “Larger” to him meant 10″.

That’s a lot of dick.

He claimed that he and his friends, two of whom had 10″ penises and none of whom had less than 8″ of cock, were looking for a woman who’d be willing to entertain all of them.  I asked if he has some sort of rule about the penis size of the guys with whom he hung out, and he swore it was just a coincidence.  I responded that I would have to work my way up to taking two 10″ cocks in me, but that I was certainly willing to try.

I was willing to try provided we all had chemistry.  The guys had done the sort of thing together before, he claimed, with a female friend who knew they were all “larger” and who took on the challenge.  Unfortunately, she had moved away a couple of months before.

I said we could meet to see if we got along and then I could meet the other guys.  It was convenient since we were in the same neighborhood.  I also gave him suggestions for finding other ladies willing to entertain the group since it’s always good to cast a wide net.

He asked about my measurements.  When I told him my bra size he said it was hard to believe.  Harder to believe a 34DDDD rack – something for which bras are mass manufactured – or a 10″ cock, something that’s seen mostly in movies?

To be continued ….

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

[Another of the Viking's stories that has been on Fleshbot.  I suppose they like the dirty stuff.]

We were both so horny that we groped and kissed only briefly before I forced my cock into her. We fucked primally for a while before I pulled out and made my way down to her pussy, leaving a trail of wet kisses.

I spent time using my mouth on her pussy before pushing her legs up and forcibly holding them with a hand behind each knee. With her like that I had full access to her asshole, and took full advantage, licking and tonguefucking with abandon. This continued for some time, rolling her onto her side then her belly and slipping 2 fingers into her pussy as I continued tonguing her ass. I love how she pushes her ass back onto my face when I have my tongue in her ass. So deliciously crude and nasty.

But after continuing that for a while, I rolled her onto her back and put my cock back into her pussy and pounded her until we both lie there, sweaty and breathing hard. After catching our breath, she rolls over onto her knees with her shoulders on the bed, ass in the air. “Put it in me from behind.”

That view of her pussy and ass is so exquisite that I had to take a moment and worship with my mouth once more. But only for a moment, before I slipped my cock into her cunt. As I fucked her, I teased her asshole with my thumb, eventually pushing it all the way in. That got a very favorable response. I continued fucking her ass with my thumb until she asked for more. I slipped my thumb out and replaced it with a finger. I added another and started rubbing my cock which was still in her pussy.

In time I slipped my fingers from her ass and replaced them with my cock, eventually coming deep in her ass.

“You’re not finished yet,” she said when I pulled out of her ass. Silly girl. I had no intention of being finished with her yet. She flipped onto her back and grabbed the Hitachi. I lubed up a couple fingers and slipped them into her pussy. Two, three, four. In to my thumb, then all the way out, twisting all the while, stretching her and opening her for what was about to happen.

I added more lube, tucked in my thumb and slowly pushed the rest of my hand into her. I love that point the first time my hand is going into her, when the base of the thumb clears and my whole hand gets sucked in.

I fisted her and, as usually happens, started playing with her asshole. I soon had 2 fingers in her ass in addition to the hand in her pussy. The fingers in her ass, palm facing up (and toward my other hand), let me rub the hand in her pussy. That was mind blowing. I spread the fingers in her ass so that I had one on either side of my other hand.

Soon I was pounding her with my hand: pulling all the way out before thrusting it back in. The whole time with those fingers in her ass, feeling every move of my other hand. Then, with a little rearranging of my hand, I started rubbing her gspot with a couple knuckles. Between the Hitachi on her clit, my hand in her cunt, and my fingers in her ass, she was soon trashing and bucking and screaming through her orgasm.

She’d finally had enough, and we soon had fallen asleep in each other’s arms.

©2012 Random Rim Jobs. All Rights Reserved.

I woke as she came into the bedroom to join me for the night. She slipped off her PJs before climbing into the bed, which is generally an indication that she is looking for sex. How could I refuse? We kissed for a bit, caressing and groping each other. I was rock hard by the time her hand found its way to my crotch.

“Mmm,” was all she said before moving down to take my cock in her mouth. She quickly had me moaning from what her mouth was doing to me. She sucked me and handled my balls, squeezing and pulling, driving me wild.

After a time she sat up on her knees, and swung a leg over me. She grasped my cock and positioned her pussy over it. She used her weight to force my cock into her and proceeded to rock and grind, making me arch to try to force my way deeper into her. She moved off her knees and onto her feet, leaning back to steady herself with her hands on the bed. Now she had even more control and raised and lowered herself over the entire length of my shaft. It was exquisite.

“Now it’s your turn to work,” she said before letting herself flop backwards onto the bed.

She lay on her back, legs splayed. I knelt before her. Moving between her legs, I slid my cock into her pussy. We fucked. Slow, fast, gentle, hard. I grabbed her breasts, one in each hand, the way rope would: close to her chest and encircling each as much as possible. They’re so wonderfully ample that I can’t get my hands anywhere near completely around them. I squeezed. Hard. I leaned down to give each nipple a brief suck and tug with my teeth. I shifted my grip to place a hand on the front of each breast and squeezed again. She moaned. I moved my hands away but she grabbed my wrists and placed my hands back where they were. “Ok,” I thought, “I can have fun with this.”

As I continued to fuck her, I squeezed and kneaded her breasts. I put weight on them & on her chest, crushing her into the bed. I grabbed them roughly, puling on them: not the nipples but rather a full handed grab. I used her tits as handles to pull her towards me as I pounded into her cunt. I could feel my orgasm slowly building, peaking slightly and falling off. Then peaking a bit higher, then higher until it washed over me with an intensity that I don’t recall feeling for a long time, if ever. I let out a primal, incoherent noise as I came, emptying into her. I really don’t remember ever having that intense and completely ecstatic of an orgasm before.

I continued my rutting as wave after wave of pleasure flowed through me and out my cock. Finally spent, I slipped wetly from her and collapsed on the bed.

We cuddled and talked. As we did, my hands wandered over her gently. She lay next to me on her stomach and my hands found their way to her ass. My fingers idly slipped between her ass cheeks which were slick with our mingled juices. I massaged her asshole with a fingertip, before moving further and slipping a finger into her cunt.

As I explored her with my finger she shifted to spread her legs for me, while half heartedly protesting that I should sleep. Too late for that. And I had had such a wonderful orgasm, I felt compelled to ensure that she was adequately rewarded.

I tossed back the sheets and she rolled onto her back, legs wide. I settled into my favorite place of all, and kissed her deeply. Licking her clit, I began fingering her: rubbing and probing her gspot. I could feel her pussy grabbing my finger and I added a second. Then a third and a fourth in quick succession. She was so aroused and relaxed that in no time I had my whole hand in her. My tongue on her clit made way for the Magic Wand.

I fucked her with my hand, pounding into her. Going slowly when she needed me to. Being brutal when she needed that. As is usually the case, my now hard (again) cock found its way into her ass and I started assfucking her while continuing to fistfuck her cunt.

Soon she came, arching and bucking. My cock left her ass but I continued fucking her with my hand until her eruption subsided and we both lay there, exhausted and satisfied.

True story.

[This has been featured on Fleshbot.  They seem to like the dirty, sexy stories.]

©2012 Random Rim Jobs. All Rights Reserved.

That’s what the Viking said when I showed him this picture.  I wanted to know if I had used it here before so I asked if he recognized it.

“I don’t know, but that looks like fun,” he said.

He’s right.  He often is.

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

I recently came whilst thinking of this photo.  Except for her yucky fake nails everything in this photo looks great.

While I’ve had plenty of experiences with something in my pussy whilst something is in my ass (great orgasms), I’ve only had one actual double penetration with two cocks experience.

A lot of the reason I’ve not done it again is because of the guys.  Guys are squeamish about other penises in the room.  I’ve heard guys talk about double penetrating a woman only if there could be some sort of barrier so they didn’t have to look at each other, as if looking at each other while their cocks were in the same woman would be “too gay.”  How much more of a heterosexual sex act can it be than to have a man’s penis inside a woman’s vagina and ass?

I’m of the opinion that whatever anyone wants to do provided consenting adults are involved is fine.  But it can be difficult to find two consenting adult men who are willing to fuck me simultaneously.  That’s ok; I don’t plan on dying anytime soon so I have time to fulfill all of my fantasies.

In the mean time, thinking of this photo will continue to put me over the edge.

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

We’ve developed opposable thumbs, which have given us all sorts of biological advantages.  One of them is the ability to penetrate the anus whilst fucking the pussy.

Sure any of the other four fingers can easily penetrate the anal opening under similar circumstances, but the thumb is uniquely positioned to really get in there without the other fingers in the way.  We’ve all had a finger or two in an ass or a pussy and lamented having to bend those unused fingers back just to get in deep enough to give him or her the pleasure you know you can if only you can get in deep enough.  Well, the thumb has no such problems.

The thumb’s problem is that it’s not long enough.  But that’s minor, and some people have longer thumbs than others.

And there are of course toys.  Many, many toys are made for the ass.  Just be sure they’re flared at the base since the ass is a lot longer than one would think.  Of course you’ve heard the horror stories about things that have gotten “lost” in asses that required medical intervention to be removed.  Also, glass jars should not be placed in the ass.  There are glass anal sex toys which feel very good, but they’ve been properly treated so they don’t break easily.

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

I’ve had this photo for quite a while.  Every time I look at it I get that fun and familiar feeling in my pussy.  And ass, of course.

This just looks like fun, and I know from my limited experience that it is fun.  Regularly I do a modified version of this, with toys.  A very fun activity when I’m all alone it putting the njoy Eleven in my pussy (I’ve yet to get the nerve to put either end in my ass.) and the small end of the njoy Pure Wand in my ass.  I do this while the Magic Wand is on my clit.  Yes, this does make me come very hard.

So every time I see this picture, it makes me think of the fun I could have with a cock in each of my holes.  I will most definitely do this again, only I won’t have the long fake nails.  Also, there will probably be more body hair involved.  Possibly also more melanin, just not on my part since I wear sunscreen with SPF 70 on a daily basis.

Double penetration, please.  In my ass and in my pussy.  Something in my mouth at the same time might be nice, but I wouldn’t want to request that without knowing whether I like it.  I like a cock in my pussy and another cock in my mouth; that I find particularly pleasurable.  Perhaps I’d like another cock involved in that scenario.  But I don’t want to make any promises.

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

April 15 looms large in the minds of Americans because it’s the last day to file and pay taxes.  I had e-filed and paid both federal and California state taxes the day before so April 15 itself was not a day of panic.

Instead it was a day of fuck.  The day of fuck.

The day of fuck began, as all days truly do, at midnight.  The ‘mate and I had received Liberator’s Wedge and Ramp and were using them for the first time.  The cover of the Ramp already needs to be washed thanks to our April 15 activities.  The Ramp was very helpful when the ‘Mate went down on me.  I could lie back so my pussy and ass were on full display at the top of the ramp.  My legs flipped back to get those pesky things out of the way.  The ‘Mate went to town licking my ass and pussy.

Then, as is my wont, I wanted something in my pussy.  Something big and heavy and hard:  an NJoy Pure Wand a friend had so kindly loaned to me.  The Viking (who is also the ‘Mate) was happy to accommodate me.  He fucked my pussy with the Pure Wand.  Then, because when I’m in a mood like that I want more, more, more, the ‘Mate was nice enough to put his cock in my pussy.  Along with the Pure Wand.

At first he fucked me with his cock and continued to fuck me with the toy.  Then, because the Pure Wand is a really great toy, he realized he could leave it in place without fear that it’d fall out or get in the way.  This allowed him to concentrate on making his cock feel good in my pussy and up against the Pure Wand.  His cock and the Wand were happily cohabitating in my pussy.

Yes, it felt fucking fantastic.  The Wedge and the Ramp have found a place in the bedroom.  They can’t fit in the drawer o’ sex, but they fit nicely next to the dresser in which the drawer o’ sex is located.  And I’m gonna have to get me one of those Pure Wands.  [That Amazon Wish List button does work, folks.]

[To be continued ….]

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

Dammit, he’s right.  I hate being a chickenshit.  But I also shouldn’t have to do all the work.

And I really do think people are playing jokes on me when they say some things, like they want to fuck me, or I should do things on webcam, because who would want to see me?  [This is NOT an invitation for compliments!]

Altar Boy called.  We’d not talked in a while, but it was nice to hear from him.  It had been a period of guys coming out of the wood work.  The nice thing was that the guys who emerged were guys I actually wanted to fuck again.

I met him and his friend out by the taco truck.  Then I took them up to the roof.  As is inevitable with me, the topic of sex came up in some capacity.  I assumed Altar Boy explained to his friend how we knew each other – met through Twitter, fuck – and geared my conversation accordingly.

Then they asked to see my apartment.  Altar Boy had already been in my place, several times, and really, it’s not all that, so I suspected this was some kind of ploy.  My place was a mess; I was embarrassed to have them see it.  Nonetheless, the three of us went to my place.

We were still talking about sex and being generally flirty.  It was a week day so I didn’t know if or when they had to get back to work.

I never said, “Would the two of you like to go upstairs and fuck?”  But neither did either of them say, “Let’s all go upstairs and fuck.”

Every once in a while I play a little game with myself where I don’t say what I want to see if someone else has the balls to say what he wants.  I did it the other day in a bar.  I was alone in a dive bar having a couple of drinks.  A guy sitting two bar stools over was clearly checking me out with the furtive glances of a shy guy.  I looked back and allowed some very obvious lingering glances.  The guy wanted to talk to me.  I wanted to talk to him.  But I decided I would let him move over one stool and begin the conversation.  I left without ever talking to him because he didn’t have the balls to talk to me.

The day in my apartment with Altar Boy and his friend was one of those times when I knew what they wanted, I knew what I would have done, and I decided to let them articulate their desires.  They never did.

Well, not completely.  I saw them to the door.  When they were about to leave they suddenly had the desire to see my tits.  I showed them my tits, but I wasn’t about to suggest any more if they weren’t going to do so.

They left.

Afterwords, I mentally kicked myself for not being ballsy.  But at the same time I didn’t think that I should have to do all the work to get a couple of guys to fuck me in all my holes.  I texted them to come back, but was told that it was too late, that I had choked.  I hadn’t choked, they hadn’t stepped up to the plate, dammit.

The friend texted me a few times, claiming he’d never had anal sex and wanted to give it a try.  I told him that he had make arrangements to make it happen.  He and I still have never had any sort of physical contact, much less sex of any sort.  I’m not holding out much hope.

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.

[Continued from "Holiday Cheer (Part 1)."]

Whiskey Dick showed up at Mary and Jack’s place.  He had been drinking.  CK and I had been drinking.

We chatted.  CK knew already how Whiskey Dick and I had met (Craig’s List, of course) and the nature of our relationship (fucking) and thought it was hilarious to quiz him on various things about me and us.  She seemed to think that because we were fucking and we liked each other that we should be “together,” whatever that meant.

Whiskey Dick and I were very comfortable with our arrangement, though things were a tad strained since he moved to a place not quite so convenient as a block away from my place.

The three of us were having fun.  I’m not sure who suggested it, but we decided to put on some of Mary and Jack’s porn.  We had the porn on in the background and continued to talk.

Porn being what it is, we were all slightly distracted from our conversation.  When the scene onscreen was a poolside threesome with two guys and a woman with the woman on her back, CK asked something along the lines of, “Why do her boobs go to the side like that?”

CK had huge breasts so I was a bit confused as to why she didn’t understand what gravity does to (natural) breasts when supine.  I tried to explain it to her.  She couldn’t comprehend.  She said her breasts didn’t do that when she laid down.  Really?  How could that be?  They’re huge and gravity is a constant force.

Of course Whiskey Dick took this as an opportunity to ask to see her breasts.  I had never seen them before either and was curious as to how they defied the forces of nature.

They did.  While very large – at least a G or H cup – there was little difference between bra-ed and braless regarding location.  Her gigantic breasts were high and firm.  And her pink areolas were the size of those seen on breasts a quarter of the size.  Her nipples were tiny as well.  CK had fucking amazing tits.

I was still a little irritated at CK’s lack of understanding about the plight of gravitational forces on fatty protuberances, but Whiskey Dick had no problem getting past that.  He was in boobie heaven.

He asked if he could touch her breasts.  He asked if he could touch my breasts.  At one point he had one hand on hers, one hand on mine, and both eyes on the porn that was still playing on the television.

Eventually she and I kissed.  We had been friends for years, and I never hid the fact that I was bisexual, but she was pretty uptight about girl-on-girl action, or anyone perceiving her as anything but straight.  I chalked it up to CK’s paranoid father, who CK said would burst in on childhood all-girl slumber parties to make sure there wasn’t any hanky-panky going on.  Apparently his mother was a lesbian and his worst fear was that his daughter would be as well.

So when CK and I kissed I think it was sort of a big deal.  For both of us.

We moved into Mary and Jack’s bedroom.  CK put on a pair of Jack’s pj pants and refused, despite pleading on my and Whiskey Dick’s parts, to take them off, ever.  Without vaginal penetration we had a threesome.

Whiskey Dick wanted to go down on her but she continued to refuse to take off her pants.  What CK did want to do was suck cock.  She was quite an enthusiastic cock sucker.  I recall thinking that she was enjoying herself a lot.

This was before I liked sucking cock so much.  I liked to suck cock, but it didn’t make my pussy wet and tingly like it does now.  This was before I had fully embraced cocksucking as something I enjoy rather than something I do for the guy’s enjoyment.  I believe sucking Whiskey Dick’s cock made CK’s pussy wet and tingly.  Which of course we never found out because of those fucking pj pants.

It was very late/early.  CK went to another bedroom to go to sleep.  I wanted to make sure she was ok and not freaked out by the whole incident.  She seemed ok.

By the time I got back to Whiskey Dick he was asleep in Mary and Jack’s bed and snoring quite loudly.  I woke him and we left.  In the wee hours of the morning the sun was bright and the cabs were scarce.

We walked toward my place while we looked for a cab.  Whiskey Dick could not get the huge grin off his face.  He kept saying, “That was so cool.  I’m so lucky.”  If he didn’t like tits before that night, he certainly did after.

Eventually we made it back to my place where I took care of my dogs.  I told Whiskey Dick he could sleep some at my house so we crawled in bed.

Only we weren’t ready to sleep.  All night long we’d both been denied good, old-fashioned fucking.  We were still horny as fuck.

Whiskey Dick and I generally had really good sex.  That morning he fucked my ass while I had a dildo in my pussy.  I came good and hard after all that build-up.

That might have been the last time I saw Whiskey Dick.

CK made me promise not to tell Mary and Jack what we’d done in their bed.  I kept that promise – for a while.  After CK and I had a falling out and were no longer friends I didn’t feel the need to keep her secrets any longer.  I certainly wasn’t ashamed of what had happened, and I told Mary and Jack something I had done.  I apologized to Mary and Jack for mistreating their bed without their permission.

I swear.  True story.

©2012 Random Rim Jobs. All Rights Reserved.