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I swear. True story.My Buddy Ozzie (Part 8)
Posted on March 22, 2011[Continued from "My Buddy Ozzie (Part 7)."]
It took a few days, but I finally got another response from the scholar Ozzie:
Are you still writing me bitch?? I told you to stop writing me! Im not interested in you or what you have to say loser. Your boring and annoying as well. I do not want to hear about my grammar bitch. No one asked for your fucking opinion. You writing is amateur at best. You write like a dyslexic substitute teacher, grading papers! Your writing is devoid of any wit or dimension. There is no structure to your writing. You cannot match wits with me….Your too fucking stupid and incredibly corny! Seriously you writing is so fucking bland and corny! Why are you so obsessed over me? Is your life that pathetic? Get a job. Stop collecting cats. Lose some weight.I feel so sorry for you. ha! I would have answered sooner, but i was in Geneva, for a romantic cabin getaway for two days with a woman I met on……….CRAIGSLIST!! Unlike you I have a life and don’t spend my entire time online. You see my menatlly retarded and emotionally insecure deficient( did not mean to insult the retarded. They have class unlike yourself), you are suppose to use that social networking site for dating, networking, etc…not for correcting grammar you annoying fat bitch! Social misfits like yourself , who are emotional insecure,should just shut it! No one, including me, gives a flying fuck of what you have to say loser. I get the last word got it loser! You started this and now I will finish it. You are now officially spam. I will no longer read or respond to your pathetic, horribly written emails. Life is too short to waste time on pathetic losers like yourself. Yes you are now spam. How ironic and poetically justified. Spam is useless and serves no real purpose. Just like you! GET A LIFE! LOSER!
It was just more of the same bullshit regarding what he decided I was. There was also new stupidity. Craig’s List isn’t a social networking site. I’m not even sure how he can type so poorly and erratically, with random spaces and multiple periods. I responded thusly:
You are a lying sack of shit. I know what you look like, and it is not pretty. You look like you get beauty and fashion advice from guys on “The Jersey Shore.”
You, dear readers, may wonder where I got off calling Ozzie a liar or claiming I had seen what he looked like. Let me take you back.
One of my dear readers took it upon himself to write to Ozzie. I had, after all, posted his email address, and y’all could have done with it as you wished. This reader did as he wished. He wrote to Ozzie as Wendy, a 38-year-old blond woman who worked from home. “She” got this picture from Ozzie:
Isn’t he cute. Yeah, I didn’t think so either. He’s wearing a baseball cap, which leads me to believe he’s balding. He’s also wearing a wife beater, which leads me to believe if he had a wife he’d beat her. If you look closely, you can see that his upper arms are hairy, the kind of hairy that indicates his back is also hairy. I know what a guy with a hairy back looks like, and Ozzie is one.
Look also at the rest of the photo. His mirror is dirty and his tacky towel rack is empty. How can I tell the towel rack is tacky? Because that’s the type of towel rack I had in my shitty rented apartments when I was a kid. To some an empty towel rack doesn’t mean anything, but to me it means this guy’s bathroom has wet, mildewed towels on the dirty, hair-covered floor. I promise Ozzie’s toilet is disgusting and his whole bathroom smells of urine.
Other than getting his photo, “Wendy” got some juicy information out of Ozzie. Wendy was sexually adventurous and Ozzie responded to that. He wanted to go on an outing to a cabin with Wendy and one of her hot chick friends. Apparently Ozzie is really into cabins. That must be a Midwest thing.
Ozzie revealed that he wasn’t into getting pegged, but that he really liked ladies with generous asses to sit on his face and smother him. He was into two women overpowering him. Aren’t they all? His favorite position was reverse cowgirl, which makes sense since he liked asses and to not acknowledge that women are humans.
Ozzie also revealed that he wouldn’t mind getting his ass fingered and wanted to try golden showers, something his ex-girlfriend – the only one he’d fucked over the last two years – wasn’t into. And he was into feet.
He claimed he had a thick cock, but I find that hard to believe. He’s just dumb enough to oversell and under deliver on the size of his penis.
One of his many fantasies was to “to propare a meal in the nude and we fuck on the kitchen table and I bend you over doggy.” So hot! Is “proparing” preparing with propane?
Ozzie claims to be done with ShazamChi, but he seems to really think Wendy is a woman who’s interested in him, and there may be someone else ….
I swear. True story.
My Fantasy Date with Shazam
Posted on February 06, 2011[This was submitted to me a long time ago. I didn't post it sooner because, well, I find it repulsive. But because I need material and because this is a good example of what I don't like, I thought I'd post it. Everything in italics is mine.]
At first, I’m a little shy – not the casual cool I tend to be – but her tweets and blog have gotten me hard and gotten me off so many times, I’m nervous. I also feel as though I need to impress her. I don’t want to be another run-of-the-mill blog-spot about how I was lame in bed when I try to get a hold of her for another encounter.
We go for drinks and I start to mellow out, relaxing and staring at her gorgeous ass is starting to give me a semi. I can’t take it anymore, I need to have her. I masturbated to the idea of the things I’d do to her last night. I was extremely excited but still maintained a nervous edge. Butterflies. Just be cool.
“Why don’t we get out of here and you can sit on my face?” I say, in my care-free tone, persuasive body movement. She’s a good little slut and agrees, we go back to my place.
Just as we enter the front door, we start making out. I’m not big on kissing, but people tell me I’m good at it.
I pull down her pants and her thong and spin her around, grab her hips and on my knees I start to lick her asshole, parting her ass cheeks with my hands and enjoying every single lick.
I lay down and pull her on top of me, her ass is smothering my face. It’s delicious, my cock begins growing in my pants and she reaches down and undoes them, moving my boxers aside to get to my raging cock – it’s small, 3.5 inches. I hope she doesn’t mind. [She does.]
She grabs and strokes it with her hand, but I reach under her and move her hand aside and hold her still. Enjoying her gorgeous ass.
After a few minutes I lift her up just enough so I can speak. “Now, you can suck it bitch!” She leans in and starts sucking [Uh, no she wouldn't.], I slide my tongue from her asshole to her delicious little pussy. She’s so moist and has an amazing aroma, just how I’d imagined it. I kiss her inner thigh, licking it and then suck on her pussy lips. She moans gently and finally I attack her clit with my tongue. Her mouth is so warm around my cock and she sucks it so well, I could cum [sic] instantly.
I lift her off of me and push her down on the floor, she gets up into the doggy style position and looks back and smiles. I twirl my index finger around her moist little asshole and then insert it. I insert a second finger and then a third, her asshole is soft and stretched [which he needn't have bothered to do considering the size of the penis]. She’s moaning gently and still smiling.
I bend down and shove my dick in her ass, fast with no remorse. She loves it, I know she does. She blogs about being an anal whore. The depths of her asshole are surprisingly tight. I fuck her, pulling her hair back and slamming my cock into her gorgeous ass. She’s screaming, she loves my cock [She would not love that cock.] – good for her. She’s behaving nicely. I could fuck her ass all day. I grab her hips and lift her up a little, slamming my cock into her harder and harder. She’s bucking.
Her pussy starts squirting onto my hard wood floor. [This is clearly a guy who doesn't understand pussies and squirting.] I pull my cock out of her insides [What a gross way to describe that.] and move to the couch. I bend over the couch and she instinctively gets on her knees and starts eating my asshole. She’s very well behaved. I reach back and hold her head in my ass. It’s never been eaten so well. I could come from this alone. She spits on her hand and reaches under me, grabbing my cock and stroking it in motion with her soft wet tongue. I don’t want to cum [sic]. I want it to last forever.
I stand up, she keeps eating my ass. Her tongue slides up and down my asshole. I move away and go to the closest and pull out a strapon, she smiles with glee. It’s 12 inches long and 3 inches wide. She reaches for it, but I hold onto it and shove it inside her wet cunt. She moans out but she takes the entire thing, I pound her with it while I rub her gorgeous tits.
Her pussy sprays again, all over the sofa this time. I’m going to need to hire a maid to clean up her puddles.
I give her the strap on and she fastens it to her waste [sic]. I lean down and suck on it, taking as much as I can until I gag. Getting it as wet as possible. I reach behind her while I suck it and finger her ass. Finally, I give her ass a swift smack and bend over the sofa. She pushes it in me and I could almost scream, I grab the couch. I’ve never been fucked before, but I want to impress her.
After a minute or two, it feels great. I start moaning, she tells me to stroke my cock and be a good bitch.
She keeps pounding, relentlessly. I’m going to cum [sic], I can’t hold it anymore.
I moan “I’m cumming, I’m cumming,” and she stops, ripping the brutal dildo [Oh, those brutal dildos!] out my ass and she bends over. I push it [Which "it," the dildo or his cock?] in her ass and shoot my load deep inside of her. [Oh, his cock, what there is of it.] She looks back smiling again and after my cum [sic] is drained into her ass she tells me to lay down. I do what I’m told. She squats over me. Her ass hovers over my face. She rests her hands on my stomach and asks if I’m ready. “Keep your mouth open,” she says.
I open my mouth and her asshole starts to pucker out. My cum [sic] comes dripping out of her ass and directly onto my tongue. I swallow it. It tastes amazing. She lowers her ass and I instinctively clean her asshole with my tongue. She’s still pushing and starts to piss on my chest. Uh, my best shirt but it was worth it.
She stands up and I stand up. She puts her pants on, fastens her shirt, leaving her panties on my floor for me to keep. She looks at me and gives me a big hug and a kiss on the cheek. She smiles and walks away without saying anything, she walks out the front door. I hope she calls me back for a return encounter.
[Uh, gross. This would most definitely not be a good date for me.]
Alameda Guy (Part 3)
Posted on December 01, 2009[Continued from "Alameda Guy (Part 2)."]
We saw each other when we could, which wasn’t often considering on many weekends he was in charge of his kids. We talked about getting our dogs together for a play date but nothing came of the talks.
One time he came over with his overnight bag, which wasn’t unusual since he had spent the night several times before. But that particular night was different because he had a harness and a dildo in his bag.
Of course we had talked about me fucking his ass many times before, but had never had the equipment to do so. But that night he had planned for it to happen.
After he showed me the goods I made him leave my bedroom so I could put on the harness in privacy. There is not much more awkward than putting on a new harness for a strap-on and I certainly did not want him watching my clumsy attempts.
I felt like I should have had a certain amount of confidence if I was to be fucking his ass. Which I did. Fuck his ass. There is something so so nice about the look of ecstasy on a man’s face when something is in his ass.
However, I was a tad disappointed at the size of the dildo. Alameda Guy had supplied it, and we had previously discussed that he should be comfortable with the size of whatever went in his ass, but I’m a size queen and truly do think bigger is better.
Especially if I’m the one with the cock. I’m pretty sure if I was a man I’d have a big cock. This is partially due to fantasy and partially due to what my mother told me.
My mother was always what’s called an oversharer. I recall she would often tell people some very intimate things when she first met them. (No, it hasn’t escaped my notice that this could be considered oversharing.) Her sharing was to the point that it made others uncomfortable, only I didn’t realize it when I was a child since I didn’t know anything else.
By the time I was in my late teens I had figured it out. When I was in my early twenties I accepted it. When I was 23 she and I took a trip to Arizona to go to DJ’s wedding. (DJ was one of my mother’s exes.) DJ lived several hours’ drive outside of Phoenix in the White Mountains.
During that drive Mom and I got to talking about life and sex and stuff. I had known since I was quite young that my mother and my father married because my mother was pregnant with my sister, and that four years later my mother got my dad drunk on a camping trip with the specific intent of conceiving me. The night we drove into the White Mountains she told me that she got pregnant the first time she and my father had sex, and that she had conceded to sex with him because he kept his hands off her tits when she told him to do so.
She also told me that he was well endowed. If only I could un-know that knowledge! I don’t want to know about my father’s penis in any way. But I do, so I know if I were a boy I’d probably have a big cock.
The night with Alameda Guy I had an incredibly average cock. I really didn’t feel like it was me. Nonetheless, I persevered and fucked his ass good and hard.
Then, when I still had my cock in place, Alameda Guy fucked my pussy. That was extra hot. There was this thing in the way between us but he was still putting his cock in my pussy. I liked that a whole lot.
And so did he. Until the dildo broke. Since “my” cock was still hard (since it couldn’t be any other way) the pressure from being sandwiched between our bodies broke the dildo off at the base. I felt bad, but we still had a lot of fun.
[To be continued ….]
I swear. True story.
Alameda Guy (Part 1)
Posted on November 13, 2009I met Alameda Guy through my Craig’s List “Teach Me How to Fuck Your Guy’s Ass” ad.
He responded to my ad with a photo of him and his wife. They were both cute. He and I exchanged a few emails and agreed to meet at a dive bar near my house. His wife was busy, but the first meeting would be a chemistry check anyway. Since eventually I’d be fucking his ass, with his wife’s instruction, we needed to make sure we could fuck.
We had some drinks. We got along well. He was very sweet and cute. He had taken BART from the East Bay so he had to go to catch the last train, at about midnight. I walked him to the 24th Street BART station and then walked toward my house.
I knew he was down in the station where phone reception is dodgy. As I walked home I texted him, “I could fuck your ass.” Only the reception on his phone was good, even in the underground train station, and I received a response from him almost immediately. He asked if he should leave the train station.
I told him, via text, to stop at a liquor store to get us some vodka and a mixer and to get to my place. We had very good sex. His phone kept buzzing and he kept not responding to it. He left in the morning.
We talked on the phone occasionally and tried to set up a meeting for all three of us. He told me he had gotten into some trouble the night he stayed over because he didn’t let his wife know that he was going to be out all night.
We were next supposed to see each other–and I was to meet his wife–at a group vodka tasting at Hangar One in Alameda. Not having a car it’s not so easy for me to get to Alameda, it being an island in the San Francisco Bay. BART goes to Oakland, but not to Alameda, probably because Alameda likes being suburban and inaccessible to the riff-raff of Oakland and San Francisco. Along with the difficulty of transportation, there was the difficulty of showing up at an event where I knew only one person, whom I had fucked.
Only no one was supposed to know we had fucked. The tasting they organized was with a group of their friends, very few of whom knew they had an open marriage. Unfortunately, non-monogamy amongst married folks is still closeted.
Alameda Guy and I figured out a reasonable story to explain how we’d met. It didn’t have too many details, and the general plan was to avoid the topic, or to change the subject. The point was to not let the couple’s friends know that he and I had fucked, with his wife’s consent or otherwise.
However, at the last minute my ride fell through. Alameda Guy and I texted each other that day. I could tell he wasn’t spitting his vodka tastings, as his spelling became increasingly more bizarre. Toward the end of the day his texts took a dark turn.
He texted that he was embarrassed. Then that he was humiliated. Hmm, not too good. Though he had made efforts at discretion had I gone to the tasting, apparently once the vodka was flowing, his wife did not do the same. She had been blatantly flirting and hitting on a woman at the tasting, and basically made it clear to their friends that he was a cuckold.
I’m glad I wasn’t there for that. Eventually, the wife announced that she was not bisexual, but a lesbian. They began the divorce process. I tried to be understanding, and offered what advice I could considering my own experience with divorce and my mother’s lesbianism, but with the limitation that I didn’t (and don’t) have young children.
(To be continued ….)
I swear. True story.
An Experience
Posted on August 11, 2009[Another hot submission from a guest writer, this time from Max Hunt, @M_Hunt on Twitter. Imagine this in a British accent, which shall explain some of the spelling.]
For a long time during my late teens and early 20′s I had a fantasy of being fucked in the arse by a woman wearing a strap-on.
I have no idea where this came from; all I know is that it was something that I never got to experience due to the fact that I fell in love and got married. When that all went sour a few years back when I was in my early 30s, I decided that the little list of things that I had in my head, the sexual fantasies that I had never acted upon and that my now ex wouldn’t even entertain, these were the things that I was going to fulfill.
So, I created a profile on Alt.com, advertising myself as a recently divorced man of 32 who was looking for someone to use him as their sex toy… I joined the approximately 27 billion other men in my area that were looking for the same thing and began emailing women who looked as if they might want to help me with this… weeks passed, and I had nothing to show for it. In the beginning I admit I fell into the trap of writing a basic email and sending it to each person that I happened across that I liked the look of. You know the sort of thing:
“Hi there. Just found your profile and WOW, you are amazing…. Great pics. How would you like to meet up sometime.”
Nothing personal about the actual person, just something generic that I could send to lots of people in a short space of time, in the hope that I would get a reply. As time when on, I realised that this wasn’t helping and began to change the standard email some what:
“Hi there. Just found your profile and WOW, you are amazing…. Great pics. I see that you <insert something relevant gleaned from their advertisement> How would you like to meet up sometime.”
Whilst this wasn’t much more effort, I thought that this might help me a little. Having no Internet at home at the time, I was having to do this through my work computer and I really didn’t have much time or ability to spend hours looking at profiles and working out what to say to each person… and one day my total and utter lack of really trying actually bore some fruit.
Her name was Switch_69 on the site, and by a weird coincidence her real name was startlingly similar to the on-line name that I had chosen for myself, not wanting to give my real one so openly considering what I was looking for. She admitted to me that whilst my email to her was the usual basic crap, the fact that my name was so similar gave her a reason to write. Just a few lines and with that we began corresponding. The emails were plentiful and whilst I never kept any of them, having done an Internet clean out on emails and email addresses a while back, I can remember her tone was always friendly whilst being forthright and definitely very playful.
As time went on and she got to know what it was that I was looking for, as well as me learning what she wanted and would expect from me if we met… we decided to arrange something. I was due to go on a business trip during the summer months and as luck would have it, if I made a 150 mile detour it would take me right past her house. We set a date and a time, and she promised to meet me at her door wearing a school girl’s outfit that she had, as long as I promised to come into her house, rip the blouse off of her and fuck her right in the hallway… after she had shut her front door, of course. I agreed enthusiastically… by this time it had been a good 4 months since I had started living at my mum and dad’s again, and whilst the underside of my bed was littered with lone socks, discarded after nights of frustrated passion, I hadn’t got close to a real woman since then, and in fact a long time before ….
So, I journeyed up to see her, things rattling through my head…. She had sent me a few pictures of herself, mainly clothed and non pornographic as she at the time didn’t have constant access to a digital camera or web cam, but she had managed to send me a blurry picture of her pussy–which due to the aforementioned liaisons with socks, had me very excited–as well as a similarly blurred photo of her cleavage. She had described herself in great detail as having black hair, large breasts and long slender legs, and by that time we had spoken on the phone a lot, so I knew what she was going to sound like…. She had told me what she wanted to do during the day of our meeting, how much she wanted me to fuck her, and that she loved being tied up and blindfolded whilst she was licked and played with. She told me that she had a selection of dildos that she would like me to use on her whilst she was tied up and that if I performed to her expectations she would grant my wish and fuck me with her strap on… but only if she was satisfied….
I reached her house. I parked my car and walked up to and knocked on her door….
She opened it and my first thought was how tall she was. Now, looking back, I cannot remember us ever talking about how tall she was before I met, but I was struck by the fact that she was almost as tall as I… me being just shy of 6 foot. Whilst I initially found that intimidating, it actually became a turn on as I walked into her hallway. She was dressed as promised as a schoolgirl, albeit one from St Trinians… classic slutty look, with short skirt, white blouse unbuttoned at the top so her enormous breasts expanded out of her too-tight bra, and stockings, suspenders and high heels…. She was stunning, literally the image of how a fantasy school girl should look. The door closed behind me, and I turned towards her… What happened next was a blur…
I pushed her against the wall of her hall and kissed her hard, our tongues danced around each others’ mouths and my hands found her blouse and ripped it open… She sighed as I moved down and began pulling at her breasts and when totally free began sucking on her nipples. I moved down a bit more and lifted up her skirt to find that she wasn’t wearing any underwear, making it easy for me to bury my face into her pussy and begin to lick her. Apparently, this was either too uncomfortable for her, or not doing anything and she pulled me upwards and lead me to her living room where when she sat on her sofa with her legs wide apart, I went down on her once more. I pulled her legs over my shoulders and began licking her properly, one hand using its fingers on her hole and the other pulling at her tits as my tongue lapped at her clit as hard as she told me she liked it…. With my fingers getting deeper and deeper into her dripping wet cunt and my tongue licking harder and faster, I felt her hands on the back of my head pushing me harder down onto her….
Stopping to catch my breath she took her opportunity and pushed me back onto my back and freed my cock from my trousers. Straddling me quickly she began fucking me, my cock, shocked as it was not to have man-made fibre enveloping it, enjoyed itself far too much and far too soon and quickly I came inside her…
Immediately I realised I wasn’t wearing a condom … but that embarrassment soon disappeared from my mind when she climbed off me and lead me upstairs to her bedroom…. It was a small purple room, with a double bed, TV and a dressing table. On the floor was a box the lid of which was discarded to the side showing me a number of vibrators and bottles of lubricant. She lay down on the bed and demanded that I lick her properly, which I endeavoured to… Again, it was a blur, and I remember licking her, using a vibrator on her as I fucked her in the arse, tying her to her bed and making her suck me til I was hard enough to fuck her again… Doing many of the things that I had never found someone willing to do with me previously….
After a few hours, whilst watching some porn on the TV, I broached the subject and she agreed that she would at least attempt to fuck me with her strap-on. I went to the shower and gave myself a clean up at her request, making sure to clean inside my arsehole because of the obvious….Up until that point I had only had carrots and a tiny vibrator, which a friend to whom I had confessed my fantasy had bought me, up my arse so I adopted the position with a sense of nervousness and excitement. She talked me through it…
She began lubricating me from behind, her hand stroking my cock and making me hard as her other hand rubbed and worked the lube in and around my arsehole. She then began working a small dildo inside, as she said this would help loosen me up for her strap-on. It felt amazing, it stretched me nicely and as she began working it deeper and deeper, pushing against my prostate I began pushing back onto it. Seeing this, she decided that I must be ready and climbed into her strap-on. As I lay there on all fours, looking to the side and watching her buckle it to her, I began to get nervous again… It wasn’t small, she having told me that she liked using it on a girl that she often met for fun who liked to be fucked really hard, and I began to wonder if it would fit inside me, and what damage it might do…
She stood to my side, rubbing lubricant over the plastic cock that now hung impressively between her legs. She looked at me and began telling me what she was going to do, turning me on by side and calling me her slut and that she was going to fuck me till I screamed… And scream I did. Gently at first she pushed the head of the dildo against my arse, and when it was in a nice position she held onto my hips and began pulling me back. I felt it pop inside quickly and then begin to slide deep inside. Never has the term feeling full up applied more as I felt it stretch me wide with each gentle thrust that she made. My cock hardened with each push and slowly she began increasing speed. A few times I had to ask her to stop whilst I caught my breath as I couldn’t take it anymore, but whilst she acquiesced to my wishes, she didn’t take long before she started again and eventually she ignored my pleas for rest and fucked me harder and faster. I was being battered and I was loving it…
My cock was harder than it had felt since I was a teenager and with my head buried in a pillow, she reached round to wank me as she fucked me and that was all I could take… Being fucked by this amazing woman with the hugest breasts and what felt like a monstrous cock all the way inside me, I came again… my cum shooting down onto the towel she had placed beneath me and my arse contracting tighter round the cock making my orgasm wonderfully painful….
She withdrew slowly and insisted that I retire to the toilet quickly.. which when i did I soon realised why. Skipping over the details of that, I soon returned to the bedroom to recover. As we lay there, porn still on the TV, my hands wandering over her body and grabbing handfuls of her breasts, I wondered why it had taken me so long to get someone who would do that to me, and when I would have it again.
Before long, I got dressed, having to leave for my hotel and my meeting the next day and whilst we spoke a bit after that, sometimes via email and others on the phone, I never saw her again….
It was incredible, if you are a guy you really should try it…
Teach Me How to Fuck Your Guy’s Ass
Posted on May 14, 2009I placed an ad on Craig’s List under w4mw Casual Encounters with the headline, “Teach Me How to Fuck Your Guy’s Ass.” My intent was to find mw couples who were already engaging in pegging so they would have the equipment, and so she could show me, via both demonstration and instruction, how to fuck ass properly.
I wanted a woman to teach me because she assumably had the same problem I feared–not being able to feel the phallus used in the harness. I did not want to get the equipment myself and fuck some guy’s ass without any lessons for fear that I’d hurt him (any more than he desired–which is NOT to say ass fucking should hurt; it should not).
I got many responses, as per usual with CL. A LOT of the respondents clearly were instituting the gunshot approach by responding to every listing that had been placed by a woman (or a “woman” bot). These sex hunters shoot their email buckshot far and wide without concern for their sexy prey. My ad was very specific, yet I had a number of responses from men who’d never been pegged and who didn’t have partners. Also, several responses from guys who wanted to fuck my ass. I dig getting my ass fucked, but that wasn’t going to help me learn how to fuck properly with a strap-on. Besides, I had been been the anally receptive partner countless times; it was my turn to top, dammit.
Through email exchanges I settled on one couple I could tell was experienced in the fine art of pegging. S&E live in the next neighborhood, Bernal Heights, so we decided to meet at a local dive bar, the 3300 Club. They are in their mid-30s and she and I have the same first name, so we already had at least two things in common–names and the desire to fuck her husband in the ass. We chatted over drinks, and then I went to the bathroom.
Always when meeting couples for the first time I go to the bathroom to give them the opportunity to talk about me. And check out my ass (duh). I think it’s polite to afford them time to determine whether they’re both attracted to me and whether they want to share their bed with me. I was hoping to be a guest in S&E’s sex life, so other than my participation, everything was up to them. We had already established our ground rules via email–E’s cock would not be entering my pussy–but otherwise anything was game provided we all wanted things to go forward.
I returned from the bathroom and S very sweetly told me, “We like you” with a big dumb grin on her face. So cute! What a nice ego boost to be told a couple finds me so interesting and sexy and fun that they both want to have their way with me.
Some weeks later I walked to their house for the big event. We had drinks and played with their dogs (not like that, you sick fucks). Eventually we went to their bedroom (the dogs were locked away in the garage). I was very nervous about strapping on and fucking him. They showed me their toys and S put on the harness to show me it wasn’t intimidating at all.
S with a cock wasn’t the least bit scary; actually, she was sexy as hell. She strutted around the bedroom showing off her big dick. I wanted to know how she fucked with it. Somehow, instead of demonstrating by fucking E’s ass, her cock found its way into my pussy.
It was a new sensation for me–having a woman with smooth skin and soft flesh pounding away at me with her cock. While she was fucking me from behind, my mouth found its way to E’s prick. Because of this experience I now know that one of my all-time favorite things is getting my pussy pounded from behind whilst my mouth is full of cock.
One of the great things about being fucked with a dildo is that it’s always hard. E shot his load–which I happily gobbled down–and was enjoying the after glow, all while S continued banging away at my cunt. Eventually she tired of working her hips to fuck me. Then the three of us did various things that three horny people do together until we were all exhausted.
We did not, however, ever get around to me fucking his ass. We had a great time, and I was definitely not disappointed in any way as I stumbled home, drunk on both drink and sex.
We got together a second time, and once again we got distracted from our main goal when when E’s cock went in my mouth and S’s cock went in my cunt. I think I’d choose that “position” if I had to fuck just one way for the rest of my life, though I’m glad I don’t have to make such a harrowing choice.
I was beginning to think I was never going to get a chance to fuck man ass. I lamented my fate to Mr. Zip, a friend with whom I speak about my sexual adventures at least once a week. Mr. Zip has no interest in getting pegged so he didn’t even volunteer to help me out of my woeful situation.
I was considering placing another CL ad with a similar headline until I got another email from S&E requesting my presence at their place.
I walked there a third time. S was wearing a floor-length, high-necked night gown that would have been matronly but for the fact that it was constructed of extremely sheer cotton. She looked so at-ease and sexy in the gown that I was immediately put on sex alert. Being able see her tits at attention as soon as I walked in the front door made me realize that night would not be like the previous two we had spent together. I was very much distracted by being able to see S’s body beneath the gown. S sensed this, I’m sure, because she soon went into the bedroom–removing her nightie on the way.
E and I followed her into the bedroom. This time I made it clear that I was not going to pass up my opportunity to fuck his ass; that I would be distracted neither by a hard cock in my mouth nor my twat. S helped me into the harness and assumed the role of Sexy Professor of Ass Fuck. She was an excellent instructor.
E got on his hands and knees. S pulled out the lube. She lubed up her fingers and loosened up his ass as she told me what he he liked. She talked about him as if he were merely an object, which was very fucking hot. I watched her lubed fingers slide into and out of his ass. She assured me his ass was clean and ready to be fucked. Eventually, I got behind him and slid my lubed cock into his ass VERY slowly.
E made it obvious he was enjoying himself, which I appreciated. I tentatively slid my cock into his ass as I got used to the feeling and sight of pushing into him. It felt so fucking hot to slowly slip into his pretty little ass.
And then I wanted to fuck. The harness was well-placed and I just wanted to pound his ass, hard. Harder. I grabbed onto his hips and pulled his ass toward me. I thrust, the pressure growing each time I jammed my cock into his asshole. S, and any comments she may have been making, faded into the background because I was fucking.
I was making guttural noises–fuck sounds–as I pounded his ass. His cock was so hard. I reached around so I could stroke it but he told S that he couldn’t handle that much stimulation. Only I could barely understand what was going on so she had to push my hand away. He pushed back into my cock as I thrust into him. I grabbed onto his shoulders so I could pull his whole body onto my cock; so I could fuck him even more ferociously.
Every time I checked in with him to make sure he was excited by what was going on he grunted in approval. I lost track of S and it was just me and my cock and E. Eventually E turned over–so I could fuck him face-to-face.
With us facing each other I needed to be gentler, but any thrill lost from savagely fucking his ass was made up for by seeing his face–as I continued to thrust into him. He looked so pretty. I looked into his eyes and I knew how men must feel when they’re fucking women. The look of utter surrender and pleasure on his face was wonderful.
I continued to slide the dildo into his ass until I was becoming too distracted by his hard cock. Looking down at the erection that I was causing was fucking hot. I was sorry that it was too much for him to let me bob my head down and suck it at that point. Eventually I began to hear S talking; I hadn’t realized she had been cheering us on all along.
Finally, I pulled out and lie next to him. We were both panting. I took the harness off and S took it and the dildo it contained away. I asked E if he would give me an assessment of how I’d done, but he wasn’t ready just yet; he was still processing.
I think I did a good fucking job (pun intended).
I swear. True story.
It’s come to my attention that I left y’all hanging. I’m sorry I didn’t help you blow your collective wad.
I still don’t know E’s assessment of my skills, as I’ve not seen S and E again. We’ve exchanged emails and they’ve assured me that they dig my scene, but that they’re busy with the boring life stuff.
