tagAnalThe Start Of My Journey (I Hope)

The Start Of My Journey (I Hope)

byLethaine©

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Ah where to start? How about I just share a fantasy with you, one that I have not acted upon, but that is a frequent visitor to my mind. I think that if the chance were to appear, I would likely act upon it. Please keep in mind that I'm not a writer or English major. There are going to be mistakes, please either live with them happily knowing you are better than me, or give me some input that will help me better tell my fantasies in the future. This will be a multi-part story as I share some of my deepest fantasies and desires that I desperately hope will become reality.

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Part One.

It had been another of those times where my wife's health had taken a turn for the worse, not life threatening, just life altering. It had been months since we'd had sex of any kind. As usual I hunted the Internet for my porn and erotica needs. I found myself drawn to the BI-sexual and she-male offerings again. I signed up to one of the alternative sites and proceeded to try and find someone I could exchange fantasy's with in an interactive way. I posted my profile and sent out a number of intro mailings to people who I thought would be a good or close match for my wants and needs. As usual nobody responded. You see I've done this before since we have these spells with my wife's health every 5-6 years or so it seems. I canceled my membership and just started spamming mailings in hopes of getting someone to reply before my time was up and I relegated the desires to mere fantasy status yet again.

Then it finally happened! Out of the dozens of emails I had sent out a response came back my way. I immediately responded and let them know that my membership was running out and that I really wanted to talk with them so if they were serious I'd renew just so we could interact. They actually responded within minutes of my response and let me know that they would be just as happy to exchange mail via any of the sites on the net and sent me a 'regular' email address to use to contact them if I was truly interested. They then asked me several questions that helped introduce myself to them and define what my desires were. If I met their needs then we would start fresh with both parties knowing that this was something worth the time.

Over the next couple weeks we got to know what we desired out of the situation and exchanged some very hot mailings that described fantasies from all three of us, you see I was looking for a bi couple with a 'dominant' female. I have a strong desire to be used to please a woman both by performing her commands with her husband and taking a strap on. While I had not done any of this with another person I have, for years, enjoyed solo anal play and always wanted to be used that way by another. It was something that the wife never really wanted to discuss seriously. I have a nice collection of toys that I keep well hidden and use when the proper time and opportunity strike.

Anyhow, my desires fueled theirs and we quickly decided to meet and see if things could work out in real life. So we set a place and time to meet in a very open and public area so that we would all feel safer initially. Things went far better than we had hoped for. We all felt comfortable around each other and most importantly we desired each other. So we again set up a time to meet, this time for a session. The day came and I went out to get a hotel room and give Lisa and Tony a call to let them know which hotel I was at and the room number. At that I set about my preparations, as instructed. I cleaned myself out with several enemas, and enjoyed the feelings they began to produce. After that I took a nice hot shower and touched up my shave jobs to make sure I was smooth for maximum pleasure on my part. A nice amount of lube was inserted and followed by a nice butt plug to loosen myself up and start stoking my fires. With that taken care of, I set about unpacking the toys and equipment needed to bring this fantasy night into reality. I offered to buy the toys and equipment since it was my pleasure to serve my mistress. Plus the fact I knew the strapons would be of sizes I both desired and could take the punishment from without being worried about it. I set up a few candles for the mood. Set out a cooler full of iced energy drinks and water, as both would be needed.

Everything was set up and ready to go, all that was needed was for the final players to show up. I knew it would take them a good hour and a half to get ready and get here and I had a good 20 minutes left before they got here so I busied my self with watching some porn that I brought along to keep my fires stoked high. The key here was that I was forbidden to touch my cock for anything other than using the restroom. So I had a raging hard on that was just begging to be touched. Fueled by the combination of porn, the butt plug in me and the knowledge of what the night held, my cock was drooling pre-cum at a heavy flow. Again another rule here was that there would be no tasting before my mistress got there. In about fifteen minutes I was grinding the butt plug in my ass on the bed the stimulation had me flowing like a river and panting like a bitch in heat. That was how they found me as they walked in.

"Well, well look what we find Tony! He's such a slut he's riding himself into a frenzy. This has got to stop! Get down on all fours and present my new ass to me. Now!"

I quickly dropped and sprawled myself out and offered my ass up as lewdly as I possibly could. I heard the locks engage and clothing ruffling as it was tossed aside. I watched the shadows as they came towards me, I think it was Lisa, walked over me and stood straddling my back. I felt her near my head as she began to put something on my head and then the lights went out. A blindfold! This was a major part of my fantasy where I give up control and become a toy for my mistress. Soon soft, warm hands began to trace my back towards my ass. Not so much a tease or foreplay, it was merely the journey towards a destination as they quickly found my ass and began to play with the butt plug.

"I see that you have begun to prepare yourself toy. I would think that you are ready for the next size plug, as you seem to be enjoying this one just a little too much. Tony hand me the smallest plug left on the bed so we can start getting him all stretched out. Then you can take this one in and wash it so you can start getting prepared." A sharp tug yanked the plug from my ass; a sloppy sucking sound accompanied the withdrawal. My ass felt so empty, so alive and wanting more.

Now that this moment was happening I was on fire I was so horny. An icy cold intruder pulled me back to the here and now as Lisa began stuffing me full of the next size plug. Given that I already had a large one in this one was a monster to most people. After only a couple strokes she had the whole thing stuffed in me and it was proving a little uncomfortable given how quickly she stuffed me. Slowly though that discomfort soothed into a low burn that served to heighten my awareness of my ass. I was so lost in the moment I didn't really keep track of what was going on until she had the second cuff on my ankle. When I stiffened a little she noticed.

"That's right toy, you are going to be used just like you hoped. And we decided to really give you a fantasy come true, we are adding a few elements to the fantasy that you had mentioned in others. This way you really won't know what's coming and the surprise will only add to the moment. Don't you think?"

By this time she had started to put the cuffs on my wrists as well. Once all four were on me I was led over to one of the beds and laid out on it, knees on the floor with my torso lying on the mattress. My arms were spread out and the cuffs were attached to some ropes that Tony had obviously been working on setting up while Lisa worked on me. My legs were also connected to ropes and I was effectively bound into a position that was very accessible and vulnerable. My cock was positioned so that it was at the edge of the mattress and pointing downwards, also very exposed and vulnerable. A shiver of pleasure and fear rippled through me.

I felt someone sit on the bed right in front of my face. "Looking at you like this has me all bothered toy, eat me and make me cum so I can concentrate better." With that she shoved her wet pussy into my face and I happily began to slurp away.

It became clear that I was just a toy at the moment as she began to use my tongue and face to get her off as quickly as possible. It was over soon and I was left with a sticky and sore face. After a couple minutes rest she got off the bed and I could here her sorting through the toys I brought. I heard what sounded like button snaps and I knew she was putting on the dildo harness. Oh god she was going to fuck me already? But this was supposed to be an all night type thing where we played until we dropped, but this was way to early. Disappointment mixed with the elation that I was going to be penetrated by another person for the first time. I was nearly humping the bed as she got behind me and started playing with the butt plug. Just a short time ago it seemed that the thing was going to rip me up, now I just wanted it stroking in and out of me, which she did a few short times before she removed it altogether.

"Here you go Tony, you know what to do. As for you toy, I hope that you are ready to put your feet firmly on this road you so want to be on."

With that she stuffed her cold cock into my ass. I was pretty sure she was using the smaller dildo but it was rather startling to have at least half of it stuffed up my ass so quickly. But as always that first resistance gave way to the slow fire in my ass that wanted more. After her first rush into my ass she began to tease me by slow stroking my ass as she fed the rest of the dildo to me. It was maddening the slow and steady fucking was delicious and the fact that it was another person and not just myself made it twice as good as normal. I wanted it to speed up and began to hump back at her in an effort to fuck myself faster.

"Naughty toy!" SLAP!

She spanked my ass with a few swift blows, that while not abusive, they did leave a nice warm glow where she had hit me. I was surprised at how much I liked that, I'd never thought of pain as being sexual but here I was enjoying the burn. I was panting now. She had some small mercy and picked up the pace a little bit and my cock began to throb in time with her strokes, it was amazing. The dildo was perfect just long and thick enough to stoke me higher and higher. I was really panting and huffing while I tried my best not to hump back again. Even though I liked the 'punishment' I didn't want her to know that and thus either ruin the fun or have her take it a step further and I'm not sure if I was ready for that. It soon was too much though and I gave in and began fucking back at her ramming the dildo in harder and harder. She kept up her rules and began spanking me but at the same time started fucking me harder and faster. I soon felt my balls begin to boil as my orgasm was coming up on me. I was going to cum without anyone touching my cock in a sexual way. The idea of that only served to intensify my feelings of pleasure and I let go and just rode the waves of feeling.

I came so hard and so much that I would say that I've never quite had an orgasm like that. My whole body pulsed and jerked with my orgasm. Thankfully at some point Lisa had stopped stroking into my ass and left the dildo buried to the hilt. My ass gripped and pulsed around the dildo as if it were sucking it. The feeling of being filled while cumming was fantastic and it intensified the feelings of every pulse of cum. As I started coming down from my high I felt that she had collapsed on my back apparently having had another orgasm herself while fucking me. I felt Tony's hands slip under her as he lifted her away so she could lie down. The dildo made an even more lurid slurping sound as it was pulled out of me than the butt plug had earlier and again my ass was left so empty and wanting. I was hoping that there would be more to come but was unsure just what more would happen given that she had cum a few times already, I had cum once and been thoroughly fucked.

End Part One.

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