A Wish to be Guided (part 1) First Time's a Charm
This is a true story which happened to me only days before I wrote this story. Any opinions\questions\comments can be sent to slik0405@hotmail.com. If you would like to post this story somewhere else please contact me by email first. Thank You and enjoy.
It all started a few weeks ago when I was getting really restless. I was still a virgin, which wasn't really the problem... it was just getting to the point where pleasing myself just wasn't satisfying my urges anymore. I was lucky that work had me distracted during the day, but even that wasn't working very well any more. I finally decided to try an online service for meeting people, and since I was going to do that I figured I might as well go all the way...I went for alt.com to meet someone with the same sexual interests.
I had been into the more kinky aspects of sex since I first stumbled across the BDSM scene during my routine surfing rounds when I was younger. From that moment on I was hooked, and sought out anything from fetishwear, to women tied-up, to women with extra equipment - it was all interesting and I loved it .
I set up my account and a profile and started to browse other personals. Since I am only nineteen, I am open to trying anything, a desire that I expressed in my profile. I'm reasonably fit and attractive, but I'd just never found anyone that I thought would take me where I wanted to go. First, I browsed ladies and hot listed a few, then I started to browse the men and tv\tg personals and again hot listed a few. I got bored, so I left it at that. Later I came back and sent a couple of messages to people I had hot listed earlier. Then of course, I got bored again and signed off.
A few days later I got a message from a couple of the members I had hot-listed. The first one I talked to seemed nice, but once we started chatting they seemed impatient and needy - which I didn't want to get involved with, especially given the kind of activities I wanted to try out. The second person to message me seemed more down to earth and genuinely concerned about safety and what I was willing to do. We chatted for the next few days and it got to the point where we decided we wanted to meet. Being my first time, I was kind of nervous even committing to a meeting, but figured what the hell I can always leave if I don't feel comfortable.
We chatted a bit more about what we would like to do and where we would like to actually meet. We decided on a hotel restaurant\bar to meet at, which was good since it was a public place in case anything happened that I wasn't comfortable with. During our chatting he told me to wear a couple of specific things: a butt plug and a button shirt. I didn't mind since the button shirt was easy because I only had one, and the butt plug I had got a little while ago for my own fun. But the biggest request he made was that I not "get off" for two days prior to our meeting.
During the couple of days leading up to the Friday, work couldn't have moved any slower of course. Especially since I said I wouldn't cum. On my last day before my bi-weekly day off, I got sent downtown to a meeting right after lunch so I got to go home right after the meeting...which meant I was finished for the day as soon as it was over which luckily happened to be an hour before normal. The rest of the day I kept my mind busy with TV and games just so I wouldn't get nervous or think about the upcoming meeting and thus make the time go even slower. Or worse, get excited and get off and have to accept to the 20 cane strokes I had consented to as punishment for cumming early.
We ended up chatting that night to confirm that we were still going to meet, and that he was confident in me knowing my safe words. It got rather annoying, but I went along with it because I know how important they are - especially in a stressful situation so an ingrained set of words would pop out instead of something else. We also went over what we would like to attempt while we were there.
Trying to go to sleep was difficult. I ended up staying awake a few hours later than normal but I got to sleep-in fairly late so it wasn't too bad. I was so restless and excited all day that I don't remember what I did with my time. Before I knew it, it was time to get everything ready and head out. Being that I don't travel out of my local area often, the adventure of a little road trip was also kind of cool. I had a quick shower dried off and as instructed, inserted my little friend slowly since I didn't want to use lube and chance it slipping out. I got dressed, put on the button shirt, and headed out to the car.
My drive started out ok. The traffic was decent and the car was running good. Because of habit I took a right turn instead of a left, which gave me a slight detour in my travels. Well, the slight detour added about a half hour to my drive, which I wasn't too happy about, but at least it kept my mind off what was to come. The major problem though, was that I was getting nervous that he might leave because he might have thought I bailed out on him. I finally made it to where we were going to meet and paid for parking, parked my car, and grabbed my bag of stuff.
With nervous and shaky hands I headed in. I took the long way in walking past the first set of doors and went to the main entrance just to see who was in there and give myself more time to back out. There weren't very many people in there, so only a couple of them could have been him.
I walked in and made eye contact with the first person and low and behold it was him. He calls out my online name at this point I am freaking out inside. I have never done anything like this, and the whole situation seemed kind of surreal. I sat down and he asked it I would like a drink. I readily agreed, needing something to calm me down. I ordered a rum and coke which is my favorite drink.
We made small talk, and that calmed me a little, but I was still very nervous and was wondering who was going to bring up what we were really here for. He had just ordered a sandwich and asked if I was hungry but I had eaten before I left and I would have been too nervous to eat anyway, so I said no. I think he wanted to get to it as much as I did so he cancelled his order and waited for me to finish my drink. Since I don't drink that fast, there were a few awkward silences where I think we where sizing each other up.
When I finished my drink he asked the question I had been waiting for and dreading the whole time. "Are you ready ?" Hesitant but sure, I said "Yes" knowing it was now or never. He then in a firm sure tone gave me instructions on what I was to do before he came up to the room. He made me repeat the instructions, and then handed me his car keys and set me to it.
My mind racing, I was thinking and wondering "should I run now?"
"NO! I can't. I would regret it" and I knew that afterwards, I'd wish I hadn't bolted so I continued to walk to where he said his car was located. Reaching his car I unlocked it and saw how big the items he asked me to carry in really were. Having my backpack with me, I put the cane in there and grabbed the spreader bar and locked the truck again. Walking back towards the door I was a little self-conscious but then thought "Whatever, I don't know anyone in here," so I walked in proudly carrying the spreader bar and thinking that if anyone knew what it was, they had to be both interested and jealous anyway.
The elevator ride up was quick, and I headed to the room. Once in, I placed the cane and spreader on the bed and put my backpack down in the corner. I then headed back to the door to see how to prop it open. The door was too heavy to just leave it open a crack so I grabbed the "do not disturb" sign and blocked the latch from closing. After that I headed back to the table and put on the blindfold and stood facing the window. At that point I reviewed the instructions in my head, making sure I hadn't missed anything. "Go to my truck and grab the cane and spreader bar and take them up to the room. Once in the room place the cane and spreader on the bed and set your backpack down wherever. Prop the door open so I can get in, and then go to the table and put on the blindfold and face the window."
I stood there waiting for what was probably only a few minutes before I heard the door sign fall to the ground. I tensed up getting very nervous again wondering what was to come. Somebody walked in and moved some things around. Whoever it was walked behind me, and when in a low, strong, deep voice he told me to unbutton my shirt, I knew who it was, and I was ready to comply. I undid the buttons slowly mainly because my hands were shaking, and because I couldn't see the buttons to help me out. With my shirt still on, I felt him grab my right wrist from behind, and raising my hand to my chest, he used my own fingers to stimulate my nipples to erectness. When he was satisfied that I was becoming aroused, he told me to undo my pants which I did a little more efficiently since I do that a little more often. In the same way, he moved my hand around and massaged my cock with it, making sure I was hard before the next step. While I was wondering what was next, I heard him open the suitcase I saw on the table when I walked in. He came back behind me and told to take off my shirt and he helped me with it and placed it somewhere. Next he told me to take off my pants which was kind of awkward since I also had to remove my shoes. Of course, underwear and socks followed suit quickly after.
I stood there naked except for the blindfold, waiting for what was to come next. I hear him step behind me then feel his presence, and shortly after feel a sharp pain in my left and then right nipple, making me gasp for breath at the shock and sudden contact. I had never had real nipple clamps on before, so this was a new and very interesting feeling for me which I enjoyed. He then told me to put my hands behind my head and hold them there. He left for a few seconds and returned, restraining my hands where they were, placing restraints on one wrist then the other before clipping them together behind my head.
Once my hands were restrained he guided me a few feet then stopped, and told me to stand and wait. I stood there and heard him go back to the bed and return. All of a sudden, I heard a faint `swoosh,' then I felt a sudden pain, and then another, and then one more on my ass, making me moan in pain and shock. A few seconds later, a few more. It wasn't a terrible pain, but it was hard enough to sting and probably leave a mark. He stopped and let me catch my breath for a minute as he tugged and played with the nipple clamps. As soon as my breathing was somewhat back to normal he started this time with a flogger instead of the cane. I only got a couple good hits with that before he stopped and walked away again.
I stood there still blindfolded, and still very nervous with my mind jumping all over the place to a point where I could barely focus. Before I could finish any thoughts, he came back and set some things down beside me somewhere and led me a few steps again. I heard some metal clanging together and felt a tugging on my sac. Then I felt some cold metal and he said quietly that I might feel a pinch but it will go away. He seemed to be taking awhile and finally he gave up and walked away setting the item down somewhere.
He came back and set some things at my feet. I felt him place some restraints around my ankles, and then I felt a tugging on my sac again. This time I heard a click followed by another click, and he let go leaving something attached and hanging from my nuts. It felt weird and before I could explore the feeling he told me to crouch down. At this point he attached a chain first to my left ankle restraint, then up to what he had clipped onto my sac then back down to my right ankle taking up some of the slack. I tried to stand back up but it tugged at my sac so I had to stay awkwardly crouched waiting for what was to come next. He walked away and I saw a slight flash under the blindfold and assumed he took a photo. After leaving me in the crouch for a while, he came back, this time going behind me. He started whipping up and down my legs and a couple on my back causing me to jump... and of course jumping made the chain pull on my sac, which made me grunt and moan in pain and possibly pleasure - it's hard to know.
After what seemed like only a few hits I could feel the object clipped to my sac slipping. I was not long before it fell to the floor at which point he stopped and I heard him say "Aww, now that's no fun." He walked around in front of me and reattached the object, this time a little higher, and then went behind me again and said "I'm not going to stop til you stand up straight," and with that he began whipping me again. Try as I might I couldn't stand up all the way. I tried. I wanted to make it, but I couldn't, and I received hit after hit til he stopped for reasons unknown. He walked back in front of me and encouraged me to stand up using only his deep strong voice. I continued trying for what seemed like forever until the object finally slipped off again, making me moan with a sigh of relief. I stood up straight again since my legs were starting to really ache and was happy that I could finally catch my breath.
He went behind me again and released my hands from on my head. This was an immense relief because they too were starting to really ache. He guided me forward a few steps before he pushed on my shoulders making me kneel down. He sat in front of me and guided my head to the front of his pants where I could feel his cock. I said yes wanting to sucking and caressing it even through the fabric. Still blindfolded, but now unrestrained, I was happy to help him remove first his pants, and then his boxers, finally getting the chance to lick up the shaft long and slow before I took just the head in and with a gentle suction ran my tongue around it slowly. I stopped and began licking up and down the shaft, randomly sucking up and down as much as I could take. To mix it up a little I went lower and started sucking and licking on his balls while I gripped his shaft. I must have been driving him wild and he didn't want to get off yet, so after what didn't seem like long, he stopped me, asking if I would like a break.
A little tired, I nodded, and he helped me up and into the bed.
Before we got comfortable he took hold of the right nipple clip and released it in one swift motion causing me to whimper and breath erratically from the sudden pain. When my breathing was somewhat normal he repeated that with the left nipple clip. He then took off the blindfold and asked if I was alright, to which I just nodded and moaned "yes" because that's all my mind was willing to process at that point. He set the items down somewhere then joined me in the bed where we cuddled, making me feel more comfortable than I can remember for a long time. I felt so secure, and I wanted that to never end and just relished the moment.
After what seemed like way too short a time (since I was so cozy with him wrapped up around me) he asked if I would like to continue. Of course I said "Yes," wanting to know what we were going to try but also not wanting to know since I could have stayed cuddled up that way all night. He told me to wait while he went and grabbed a couple things. He came back, and since my eyes were still closed, I don't know what he had grabbed. At this point the whole situation still seemed like a dream, the only thing keeping me from knowing the difference was the slight pain I still felt in my ass and nipples, and the fact that it was too real and well, wild, to be a dream.
I rotated on the bed `til I was facing the bottom, after which he gave me a pillow to lie my head down on, I knew what was coming next. This was for me one of the most anticipated activities we had discussed about trying during our time together. He began by applying some lube around my hole then his hand left, and shortly after I felt a cold pressure pushing on my hole and in no time he was pumping a dildo in and out of my ass. It was pushed in all the way and he let go but it started to slip out so he had me reach back and hold it in. Then I started to play with it myself. I pushed it in, and let it slide out, then repeated that a few times while I waited for what was to come.
He lubed up his hand then stopped me and pulled out the dildo, and now he slowly started inserting one, then two fingers which made me a little nervous because his hand was seemingly larger than I had anticipated. Soon he was trying for the whole had but it seemed like he didn't know how hard he could push. Before I knew what I was doing, I started pushing back harder and harder on his hand, and with every push, I inadvertently held my breath until finally his hand passed that point of resistance, after which it just slowly slid in deeper and deeper. I was moaning, and trying to catch my breath from the exertion.
I was in heaven. It was just as good if not better than I had imagined this to be. I was more full than I had ever been, and it felt exquisite. This was so much better than a butt plug or a dildo! I could feel every twitch and movement of his hand and enjoyed every second it was in there. It seemed at this point that he didn't know what to do next, and I don't blame him since I had no clue either. We just stayed like that for a few minutes while he took a picture, before he slowly started to pull out. I knew I didn't want that to happen, but knew I had to let go sometime. Once his hand was out, I felt empty, but very satisfied, and though I hadn't gotten off, I had that feeling of fulfillment and peace. I didn't -- no, I couldn't -- move. I just sat there as he cleaned up his hand and I enjoyed the moment.
He lay down and guided me again to his cock and wanting him to feel as much pleasure as I had just experienced I went to work with as much enthusiasm as I could muster from the now limited supply of energy I had left. Slowly I went at it licking up and down his shaft trying to give him as much pleasure as I could. I took my time trying to stretch out his pleasure as long as I could, switching from sucking and licking to gentle messaging and stroking, which he seemed to enjoy immensely. But before long, I think he got impatient when he moved me down so he could stroke himself, so I just pleasured his sac and anus, but before long he was about to shoot so he stopped and let me finish him off. I knew what he wanted, so I kept my mouth on his shaft with a gentle suction while I stroked the rest with my hand, and before long it was too much for him and he started to shoot his load in my mouth. I tried to catch as much as I could and only allowed a few dribbles to get away. Satisfied, he guided me up to lie beside him again.
We got into a cozy cuddle again where he thanked me for my services. My natural reaction was to mumble "you're welcome," but I really wanted to say "No, thank YOU, it was great!" but oh well. I was so tired but I couldn't sleep. My mind was going through what was happening and had happened, over and over. I must have dozed off a couple times, but most of the time I was awake, my eyes closed and happily relaxing. A little while later he started to stroke me under the covers telling me I could release my load and slowly I got closer and closer to getting off, but just before I could have some release, my mind got distracted and I couldn't focus again. I was so frustrated I wanted to scream, but it was my own fault, almost like my mind was trying to torture me more. He stopped and guided my hand to stroke myself and try as I might I couldn't pass that point. It was an exquisite torture.
Eventually I got tired and slowed, and at this point he must have known and asked if I would like to sleep or have some more fun. To this I replied "I can make it for one more session." He then asked me to come around to his side of the bed - which I did, but when I got up I had a shooting pain in my shoulder, probably because of how I had been laying on the bed. I started massaging it, and when he noticed, he asked if I was ok and I just said it was a cramp, to which he had me sit on the edge of the bed while he massaged it, which was nice. When the cramp was mostly gone, he had me stand up and again put on the blindfold, and had me hold my hands behind my head again.
I was feeling fine as he started to tug at my sac again and told me if I felt a pinch to notify him. He tied a string around my sac to make it easier for him to pull then I heard the metal clanking again. This time he managed to get the object on and undid the string but noticed it was starting to slip a little so he started putting the string back on and he got the toys on my nuts all tied up. At this point I started to feel light-headed and notified him immediately, at which point he had me sit down on his lap as I asked for a drink. He reached over and guided my hands to a cup. I took a few sips as he moved the blindfold up so I could see but I was getting worse and knew if I didn't lie down I would pass out. I lied down and immediately started feeling better, taking deep breaths. By the time I was ok again, he had taken off the metal toy and I didn't even know it. He asked if I was alright since his main concern was safety. I said I was ok, but that I couldn't stand up again.
He got up and went to grab a couple other things and came back. I saw a pair of vice grips, and he started to close one on my left nipple. Wow! Did that hurt! But once it was on and positioned it became a dull ache. He repeated that step with another pair of vice grips to my right nipple, and again it hurt a lot but became a dull ache. Once they were on he moved the blindfold back to cover my eyes. He moved the vice grips to a more comfortable position so they wouldn't slip to the sides and relaxed my arms up by my head. I felt him get up again as he went to grab something. I felt the bed move again as he came back, and he started to gently whip and flog around my cock making me jump. It wasn't that it hurt, I guess it was just a natural reaction to sudden hits on my naked cock and balls.
Closer and closer he hit around my cock then he started hitting around my balls as I was still jumping. He even teased me a little only hitting the air, and I still jumped! I tried to control myself, and managed to work it so that if I clenched my abs and curled my toes, I wouldn't jump as much. I wanted to show that I was willing to take it for him. After a few more hits, he got up again and was back shortly. This time, I felt a prickly feeling rolling over my nether region. It was a weird feeling, not necessarily bad, but definitely not comfortable, so I was squirming around trying to move...and of course, when I moved, the vice grips moved which wasn't the most pleasant of feelings. He went up and down my shaft and around my balls then up to my nips and back down before he finished with that toy.
Yet again he got up but this time went to the bathroom and I know this because I could hear him running the water. He came back and then suddenly I felt a few hot drips fall just above my cock which made me moan and suck in a sharp, deep breath in utter shock and surprise. As soon as I was breathing normal again more hot drips fell upon me...around my cock, up on my nips, and back around my cock. This was interesting not knowing when, how much, or even where, they were going to land. He finished up and blew the candle out, at which point he asked if I would like to be restrained again. I just nodded, since my mind was just not able to keep up with all the mixed feelings I was having. Was I in pain or pleasure? Did it hurt? Why wasn't I stopping him from doing this? I couldn't answer my own questions, let alone someone else's since my mind was processing just too much information and too many feelings.
Before I knew it he was back and was pushing my legs up toward my head, and I responded by hugging them to my chest. He restrained my hands again by clipping the wrists together while I was in that position. Again he started whipping me, this time on my exposed ass but soon he switched back to the cane which for some reason was now my favorite. I was hit pretty good a few times before he misjudged how far the cane sunk in and it hit my nut which made me jump and moan quite loudly. To be honest I'm surprised I didn't yell out. I kept my mouth shut and just moaned, although it was not with pleasure. He obviously knew and stopped and let me calm down. Once my breathing was calmed down and I had stopped my moaning, he asked if I wanted to continue. I nodded and mumbled a yes. Yes it hurt, but why should one mistake cut short a so far very enjoyable session?
He started to play with my ass again, lubing it up as he started to insert one then two fingers as he lubed me up some more. Eventually he was trying for his whole hand again, but this time I couldn't help him out so it was slow and he wasn't pushing hard enough fpr a quick entry, which is a really awkward feeling having something so big trying to get in without much force. Eventually he got his fist in after much squirming on my part and concentration on his. This time he moved his hand around a little more which, since my hole was already stretched, was very sensitive to this and I was in heaven loving every second. Before long, it was again time for him to pull out, but this time he went extra slow and when something as big as his hand comes out slow, my muscles were trying to force it out faster. However, whenever I pushed out, he pushed back, and I was forced to go at his pace regardless, which made the experience that much sweeter. It was an exquisite experience and while I don't know if it was good or bad, I do know it was fun.
I sat like that hugging my legs for a couple of minutes while he cleaned up. He went to the bathroom and grabbed a wash cloth and came back and wiped me down, starting at my forehead, which was nice since I was sweating. After he finished cleaning me up he released me and this time we got comfortable in bed for the night.
Throughout the night, I slept off and on, having weird dreams waking me up, but always waking up to a warm comfy embrace for me to relax and calm down in. Eventually night turned to day and before I knew it late morning. He had stated before we went to bed that it would be really nice to wake up to me servicing him. I really wanted to, and thought about moving to do it, but my muscles didn't want to leave such a nice position. Never wanting to move, I felt him adjust himself as he reached over and started stroking me. After a little of that he guided my left hand to stroke him then my right to pleasure my self. I was enjoying waking up in such a nice way so I kept my strokes slow and sensual. I could tell he was enjoying it, but eventually he started to move me down so I could pay proper attention to his needs.
I crawled under the covers to where I could properly take care of him and slowly, probably agonizingly slowly, licked up and down his shaft. I took it in my mouth again keeping it slow and sensual trying to stretch it out as long as I could, as though I was trying to repay him for such an amazing experience. He handed me a condom and I slowly put it on while I was working him over. Eventually he pulled the covers away and handed me some lube. I quickly squirted some in my hand and slowly worked it up and down his shaft then while still stroking him applied some to my ass. I then moved up so I could work him into me which went really easy because of the lube and the stretching from yesterday.
I started out slow and eventually got up some speeduntil I got a little tired and slowed, all the while stroking and massaging his chest and shoulders. He guided one of my hands to my cock and I began to stroke myself while he helped pump as I was moving up and down. I was in heaven. It was such an amazing feeling having a nice big cock up my ass while I was stroking myself in front of him. Unfortunately, because of how tired I still was, I couldn't keep it up for very long. I had to stop with him in me, and just catch my breath and give my muscles a break.
Hoping he would do me from behind, I turned around to face the foot of the bed. He got the idea and got up so he could do me right. He had me lie down flat and slid in as he lay right on top of me. I can't properly say how nice that felt having him penetrating me while keeping me pinned down from his weight. I was useless. All I could do was lie there and enjoy it which I did, readily moaning with each of his thrusts into me.
He must have been close because he stopped and lay down again pulling me over to service him. I began stroking him and slipped the condom off then began my servicing. Before long he pushed me down so I began licking around his anus and sac while he stroked himself. He was about ready to get off and guided me up again and I knew he was about ready, so I took him in my mouth and kept his head in, while I sucked and stroked him until he shot his load. This time I managed to keep every last drop and swallowed it greedily. I continued to play with him for a couple of minutes, and then moved up to that cozy embrace of his again.
What seemed like only a short time later, he told me we had to leave soon, and then a couple of minutes later he got up and went to the bathroom. I lay there, then slowly moved to the edge of the bed, stretching out my muscles and just relishing in the glow I was feeling from the whole night's events. He came back from the bathroom and I asked him if I could shower. He didn't mind, so I went and just relaxed trying to wake up enough for my drive home, as well as get all my limbs moving properly. I finished my shower and began drying off when he came in and took the towel from me and began drying me off. Having not been dried by anyone since I was about four, this felt a little awkward but I liked it: it made me feel wanted and special in that he took the time to come and gently dry me off.
Once dry, I slowly made my way back into the room to where he had set my pants and stuff the night before. I slowly began to dress as he finished cleaning up the room and putting all the toys back in the suitcase. Once I was finished and just sitting in the chair letting my mind replay and think about how I felt he came over and handed me a gift. I was speechless. After all he had given me that night, he had also gone and got me a book that he had read and told me about before we had met. I thanked him, not knowing what else to say. He just watched me as I looked at the book, then he said it was time to go and for me to grab the cane and spreader bar and meet him out at his truck. I grabbed them and followed him out. He went to check out as I walked out to his truck I set the items in and waited for him. I watched as he walked out wondering how I had found such a person that managed to make my first time the best night I had ever had. I handed him his keys and we said our good byes, and with a final hand shake I headed toward my car and spent my journey home going over what happened and how I felt.
I know the second time, and every other time will be different, with him, or with anyone else, but since he's already told me he would like me to come back, I'm looking forward to all of toys I didn't get to see the first night. Also to spending a long time servicing him, and hoping he won't get impatient and will just let me say "thank you" to him in my own way. I am especially looking forward to feeling the cane on my ass again -- because the way it feels the next night is exquisite, That fist of his was a joy to have in my backside. But most of all, I'm looking forward to sleeping in his arms, this time for two nights.