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The Start Of My Journey (I Hope)

By: Lethaine



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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.

The Start Of My Journey (I Hope) Ch. 02



Thank you for the feedback! I'm glad to hear that many of you enjoyed the story and asked for more. Well here it is more of my fantasy night that I hope to one day enjoy

I hope that I addressed the constructive feedback I received properly, Thank You.

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"Whooo Toy! That was a great fuck. Ok Tony, help him up and into the restroom to get him ready." Mistress was staring directly at me as I whipped my head around in surprise. "What, you think we are done? Oh no, no, no my sweet little Toy. That was just the first course in our buffet of kinky fun tonight!" With a wave she dismissed both Tony and I and I felt his hands lift me up off of the bed.

"We've got 15 minutes to get cleaned up and ready for the next round of play," came the whisper to my ear. "If you don't think you can handle it say the safe word now before she gets to worked up and wants more. She would be far less disappointed if it happened now as opposed to after the break and we started up again. Trust me on this."

I turned to look at him and saw only genuine care on his face. I thought for a quick moment taking stock of my body and my level of lust. I was still sporting a semi erect cock and had a desire to feel and taste more of the delights I just had. A quick shake of my head was all I gave as we entered the bathroom.

"Go ahead and take a shower, relax some and get cleaned up. I've prepared the items that we will need for the next stage. While you are in the shower I'll go make us a couple drinks so we can relax while I get freshened up after you. Once we are done Mistress will take a few moments to freshen up so we should have plenty of time to get that drink and some water into us."

He flashed me a smile as he exited the bathroom while I pulled off the wrist and ankle cuffs. I glanced over at the sink counter and was surprised by the planning that they had put into this. Everything I needed to clean and freshen myself was present and ready for my use. I turned on the shower and began the preparation rituals I was accustomed to. 

Just as I finished and was entering the shower a nock came at the door. "Is it ok to come in now?" I gave a quick affirmative and stepped in to let the hot water rain down on me and melt the fatigue away. Tony's hand came through the shower door holding a large glass of orange juice and I assumed vodka. "You want a slug of this now or should I just set it on the counter for when you are through? Oh, and don't burn up all the hot water please." 

The glass looked extremely inviting so I grabbed it and chugged half of it before the burn of the vodka caught up to me. I pushed the glass back into his hand and sucked a little air while I managed to whisper out a feeble thank you. Well, hell, if I couldn't relax and catch a second strong wind after a nice shower and that drink then there was no hope for me. A few more minutes under the water and I was out to dry and let Tony have his shower.

He pressed the drink back into my hands as he passed me for the shower, still wearing that smile from earlier. "Your new attire and gear are on the counter for when you are dry. Once I'm out I will help you with anything that you can't get yourself." 

I was confused by that and looked up to see what he meant and nearly dropped my glass in surprise. A fresh set of cuffs were on the counter along with a new butt plug, cock ring, and a penis gag. To top it off was a nice leather hood that I had never seen before. It would cover my eyes and ears yet leave my mouth and nose free. That alone sent a new twitch to my cock. 

As I gazed over these new items I noticed that the plug was a little different looking than any I had seen before and went to inspect it closer. It was a nice silicone number and was rather nice sized. What was different was the hollow space in the center, as if it were made to accommodate a vibrator or egg device. Well I had read about those, but something was nagging at the back of my mind.

Tony shocked me from my thoughts. "I suppose by now you have looked over all the new goodies I left there. I also think that you are intrigued by that new plug, and rightfully so. Mistress will show you some new delights with that, and that is all I can tell you, well aside from the fact that you will love it!" With that the water shut off and he stepped out to dry off. 

Seeing that I had not touched anything yet nor finished my drink he got an alarmed look on his face. "You'd better hurry up and get ready! Mistress will be very upset if we are not out soon and you are presentable." I nodded and tossed back the glass, wincing at the burning vodka again. I was already feeling the glow from the first half of the glass and knew that this would put a nice warm feeling in me.

Well to make the rest of that long story short, we got ready and out before Mistress got angry and were able to get a bottle of water in before she came back out. In mere moments of her coming out of the bathroom I was bound and hooded, isolated from anything but muffled sound and sweet glorious touch.

There now we can get back to the good parts.

Four hands wound their way about my body, alternating light and rough in their passing. The motions brought them so close to my cock and balls, but they would not reward me with that contact. I was so hard now I thought my cock was going to burst. Then they were gone and I was again isolated from everything, no sight, no real sound and no touch. It was so frustrating that I actually began to whimper lightly.

That whimper turned to moan as I felt something hot and soft work its way slowly across the length of my cock. Nothing else touched me but for that one hot point of pleasure, I could do nothing but pant in pleasure at the velvety wet touch.

I was lost in the world of my cock when I felt someone begin to adjust my butt plug. A quick tug and push were followed by a sharp slap to my ass. A throaty chuckle came through the hood and left me puzzled and thinking. I didn't have long to concentrate as a hot, wet mouth engulfed me and sent my spiraling into sexual orbit again. Wonderful minutes, or were they seconds, were lost to the bliss. Then it hit me......my ass was going numb and cold!

One side of my hood moved a touch and my one ear exposed. "You probably feel it by now, don't you Toy? I remembered how you said you liked to ice down your dildos for extended play, so I decided to create something for you. Well that is wrong in a sense, it is for me actually. I do hope that you enjoy it because I know I will!" A soft chuckle tickled my ear as the hood was pulled back down to engulf me in the silence of my own mind yet again. But now I knew what the cavity in the plug was for.

The mouth was gone and I groaned in frustration. Hands found my balls and massaged and cradled them gently as the other pair moved up my back towards my head and shoulders. I could feel someone move in front of me just before the hands came to my hooded head. The combination of the iced plug, ball massage and the pure anticipation had my panting open mouthed riding a cloud I'd never found before.

The hands left my balls and the plug was slowly, teasingly, pulled out. Soon hot fingers began to dance as my ass was lubed up again. I began to move my hips as much as they could in my bound state. I really wanted to be full again; it wasn't long before I got my desire. Slowly I felt something large line up against my gaping hole and begin to push in. This was much larger than what had been used on me earlier and I was both excited and nervous.

As I opened my mouth to ask Mistress to be gentle something, stiff, warm and velvety was pushed into my mouth. At last! I was finally getting a taste of cock, and was being fucked at the same time. I was in heaven and bent all of my senses to examine and enjoy what was in my mouth.

I could smell the musky, clean smell of his cock. The sweet and salty taste of his pre-cum began to explode on my tongue washing away the salty taste of skin. The head was a spongy mass that I found I loved against my tongue and I began to show just exactly how much I liked it.

I cupped my tongue around the bottom of his cock head and began a little pulsing suck and lick combo I had dreamed up while fantasizing all those years. I had always hoped that my wife would do something like that, but sadly she never put that much effort into sucking my cock, oh well. The only way I could tell that this was appreciated was by the tension of the hands on my leather bound head.

I had begun to sweat under the hood and the scent of hot, wet leather mixed with the smell of his cock. I was lightheaded, cock drunk even. I could barely register that Mistress was still trying to work that giant dildo into my ass. But it was enough that I tried to make myself relax so that I could take the gift she was offering me. I was soon rewarded with the sensation of being filled to a point beyond any I had taken myself. 

As I was losing myself in the sensation of being taken at both ends I must have slacked off of my sucking. Tony had gone from letting me suck his cock to fucking my mouth. I was thankful that he was being considerate of me and only stroking in short strokes so I wouldn't gag. I turned my mind back to the first cock to be in my mouth, and I knew then it wouldn't be the last time. I could feel his heart throb in his meat. I could feel the head as it slid over my tongue, back and forth. I was saddened a little that the taste of his pre-cum was lost in the frantic pace, but the over all feeling and emotion of being mouth fucked outweighed that loss.

All too soon his pace became more frantic and the strokes deeper as he began to swell. I knew it was coming, my first load. My cock twitched and my ass began to grab at my Mistress' dildo. I really WANTED this. I began to suck harder trying to pull it out of his balls. It wasn't long before he jerked to a near stop and pulled out so that just his head was in my sucking mouth. I knew what was to come and folded back my tongue so that I could capture it all in my mouth without being gagged by the jets. 

My reward came to me in wonderful, hot force. I felt his head expand and twitch as the first jet came barreling up for me. The hot saltiness exploded on my tongue only to be followed by more. Soon there was more than I could hold in my mouth and I was forced to swallow as he continued to jet into me. The sticky and thick cum coated my mouth and throat. The slightly bitter chlorine like taste was not as strong as my own nor was it as acidic as mine. I like this, very much and I knew it was just a start.

Even as I was lost in my own head at this new joy, my body was still concentrating on the gift Mistress was giving me. As I came down of my blowjob buzz I could completely feel what has occurring with my ass. The wonderful heat of the friction was spreading in my ass and belly. The motions against my prostate had me leaking copious amounts of pre-cum and I could feel it dripping off my cock and occasionally splash my thigh as I bounced under her. 

I could tell by her pace and the depth that she was plunging into me that she was nearing her own orgasm so I began to concentrate on my cock and try to get mine. I could feel it building quickly. I started to thrust back as well was I could to get more of her into me so I could finish. Mistress caught this and rewarded me with several sharp slaps to my ass, but I couldn't help it. I didn't stop as I was so close and wanted that release. That's when she pulled out, quickly and rudely. Several more blows rained down on my ass as I nearly wept in frustration.

I felt her move away from me and come back moments later. Something cold, so very cold was roughly shoved into my ass. The plug was back and it was colder than before. The chill sent my orgasm back into my depths and frustrated me to no end. I was going to plead for release, some mercy just as her hand began to fall on my ass cheeks again.

The side of my hood moved again as she continued to spank me. "Bad, bad Toy! You forget your place. I am in charge, don't ever forget that. I was going to be nice and let you cum with me, yet you had to be greedy and think only of yourself. For that you shall pay the price. Take of the hood now Tony, and put the penis gag in. He really seemed to like your cock, so he won't mind."

In short order that all occurred as she commanded and the table I was tied to was turned to face the bed. Mistress had her other slave come to the bed with her. He was to give her the orgasm I denied her. As she lay down after taking off her harness she looked over at me. "Oh don't worry. I'll let you have your orgasm after I've had mine. But you may not like just how I will. But then again a good slut like you probably will."

A motion of her fingers set Tony into action and he dove in to eat her over the edge. In short time he brought her several orgasms. The vision of the two of them going at it and her passionate cries kept me hard as a rock and oozing. After a handful of orgasms she pushed Tony away and again looked at me with eyes filled with the glow of ecstasy. 

She got up and went to her toy bag and pulled out a tube of some sort of lube. She went back over to Tony and began to massage it into his cock. "I bet you want to know what's going on, don't you Toy? Well I did promise you an orgasm and Tony here is going to provide it, or at least try. This gel is a desensitizing agent which will make him last a long, long time. Even without this he would last forever after cumming once already, with this he may be able to go for at least 45 minutes!"

With that she pulled him off the bed and toward me by his hard cock. Once behind me she roughly pulled the iced plug out of my ass and they waited as my gaping ass began to close some. I could feel it pulsing, wanting to be filled again. She was right I am a slut and I wanted this. Then I felt it. The head of his cock was red hot compared to the iced plug. So incredibly slow he began to push into me. He didn't have to wait since I was so stretched out already; he just wanted to tease me.

My cock was pulsing as I reveled in the thought of being fucked by a real cock. So many of my dreams were being fulfilled tonight, it was a perverts heaven on earth come to life. After an agonizing wait he was completely in my ass. I could feel his heat radiate out into my chilled ass and that only served to take my higher. I twitched my muscles as much as I was able, telling him to fuck me and fuck me good.

He slapped my ass once and began to fuck me slowly. Pulling all the way out before slowly slipping all the way back in until his pubes tickled my crack. I don't know how long this lasted before he sped up, but it felt like forever and my frustration was making me want to cry out.

Then he began to speed up. Still using the entire in and out method, but just faster. It was fantastic, so much better than me using my dildos and in a way even better than Mistress. Not that I would ever tell her that. The only thing that was not as good was the fact that he wasn't hitting my prostrate like Mistress did with her long and thick dildo. My orgasm was building, but at a slow and infuriating pace.

He kept pounding me for what seemed hours. My body was drenched in sweat and was literally bouncing in anticipation of release. My balls felt like they were going to explode even with the steady drip of pre-cum being released.

At last his pace built to a frantic pounding and the added stimulation was driving me to an edge as well. Then I felt him began to swell up inside me and knew it was there. Knowing that I was about to get another load inside me set me off and I began to shoot my load out onto the floor as he began to jet into me. I could feel the heat travel up into me and coat my insides. He kept pounding into me, lost in his release and I could feel it begin to drip down my thighs. The sheer naughtiness triggered another set of pulses in my cock and I dripped out some more come. A multiple orgasm?! And then I was lost in darkness as I collapsed exhausted.

I awoke the next day sticky and sore, but comfortably arranged in the hotels bed. Mistress and Tony were nowhere to be found, but they had left me a note on the television.

Toy. We had great fun last night and you were even better than we had dreamed of. We both hope that you enjoyed it as much as it seemed and we hope to hear from you and see you again.

Soon!

Love

M&T

A grin split my face. I began to plan for the next meeting and just what new fantasies I could share with them and see if they would be brought to life. I set the note down and waddled off to the shower humming a happy little tune.

End Part 2