Random Rim Jobs

[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…