My love affair with CMNM and eventually the love of my life

In my 20's I was a wild child. I grew up on a farm in Kansas in the middle of nowhere. After high school, I went to a community college and worked on my family farm for a few years trying to figure out what I wanted to do. The year I turned 21 I got a scholarship to Loyola in Chicago. That was the first time I was ever on my own. Just living alone and getting to walk around my apartment naked was a thrill. I actually spent most of my time at home naked, only putting on clothes when someone was coming over. I made a few friends at school, but my best buddy was a guy I met at the gay beach when I first moved to town. We spent most weekends going to bars or the beach in the summer. Ric was my age but had grown up in New Orleans so he had been exposed to a lot more stuff than me. After the first year, we decided to get an apartment together to save money. We had our own bedrooms so that when we hooked up it wasn't weird for each other. He was constantly trying to put me in new situations that would push my limits or embarrass me. I think he got off on watching my face turn red or seeing me stumble over words. We had started off as friends and then became fuck buddies. Neither of us was looking for a relationship, so when we would go out we would hook up with guys or just go home together at the end of the night. 

When he first started pushing my limits it was pretty tame. For instance, the first time I remember being shocked by him was not long after we met. We had already slept together so obviously we were comfortable around each other. We had been lying on the beach for a while and then waded into the water to cool off. We were just over waist-deep in the water and looking back at the crowded beach checking out the hot guys. 

Ric waded over behind me and subtly slid my swimsuit down to my knees. At first, I was shocked he would do that in public, then I felt the thrill and let it stay around my knees. He moved back in front of me and started giving me a hand job. That was the first time I remember him pointing out how red my face was from embarrassment. 

But the thrill of being almost public and the expert handjob had me going along with it. Once he knew I was into it he pushed me a bit further. He dipped down in the water in front of me and slid my suit from my knees to my ankles. Then in a quick motion, he pushed me backward in the water and ripped my suit off over my feet when I floated backwards.

I was laughing when I went under the water ... turning an all-new shade of red when I resurfaced trying to get my footing again. To my surprise, Ric was quickly backing toward the shore with a huge smile on his face. I tried to go after him but had to stay under the water as it got more and more shallow towards the beach. He backed all the way up and then with a devil's grin turned and walked back to our towels carrying my swimsuit. He casually tossed it onto my towel and grabbed us two new beers. He walked over to a group of guys standing nearby and started up a conversation ...leaving me standing out in the water, heart pounding, face red, and to my surprise a raging boner so hard it almost hurt.

After a few minutes, Ric headed back toward the water with a group of six guys close behind him. I started to panic and moved a little deeper to hide my hardon from view, moving out to where I was about chest deep. They got closer and closer...the thrill made my dick throb. When they were about mid-thigh deep they stopped and started chatting again. I tried to act like I was busy looking around when Ric yelled and waved me in to get the beer he brought me. 

I felt my face flush again and my heart started beating faster. This was the power Ric had over me. I just started wading closer willing my dick to get soft, but no luck. When I was about waist-deep Ric was smiling ear to ear. Then he made a show of calling me loudly " Hey! Come here...I want you to meet these guys!" And then he held my beer out towards me to come take it. I was flustered and so I tried to stay below the water as I moved toward him. Once I got about halfway, there was no way to make it any further without standing up and exposing myself to the new group of guys. Ric was loving it! He started to talk loudly and include me in the conversation so I was forced to interact.  He even waded out a little deeper until we were about six feet apart, with my beer extended out in front of him. He knew I couldn't come any closer without exposing my bobbing dick. Again he spoke loud enough for everyone to hear ( and chuckling at the same time) " ..come here and say hi..don't be rude!"  Ric waded a bit deeper until he was close enough to hand me the beer. As I took the beer he slipped his arm around my neck to hold me in place. At this point, I was barely pubes deep in the water and the tip of my dick was bobbing just below the surface of the water. With his arm around my neck, he turned us back towards the new guys and called them over to meet me. I went full red face as they got closer and closer the guy in front extending his hand to shake mine. I nervously reached out and took his hand just as he glanced down and saw my hard dick below the water. 

The interaction instantly changed with a big smile spreading across his face. As the other guys came up behind him they were forming a wall of muscle between me and the beach. With Ric's arm around my neck and the new guys shaking my hand, they pulled me another step forward towards the new guys, and with that, the tip of my dick broke the surface of the water. Ric took another step and the new guy twisted and pulled me another step until my dick bobbed out of the water and I came into full view. The only thing keeping the entire beach from seeing me naked was the five guys standing in front of me. My face was bright red and Ric loved it.

Each guy introduced themselves one at a time, shaking my hand and looking me up and down to take in the view. Nobody even asked why I was naked. They just acted like it was normal. I stood there trying to keep up with the conversation while my mind was racing. The excitement kept my dick hard and with the water level just below my balls now, I was on full display. Ric held me in place with his arm around my neck facing the beach. The six guys stayed in a line facing us with their backs to the beach. As we chatted Ric kept moving me closer to the guys bit by bit and they would back up slowly. Before I knew it we were all standing knees deep and a few other guys had waded out past us and took in the view of me naked. I was so embarrassed but turned on at the same time. I tried to maintain eye contact as we all talked but I could tell they all kept glancing at my dick. Out of nowhere, Tim, the first guy to shake my hand, said: " ..dang dude, you're leaking pre cum like a faucet.." My heart jumped into my throat as I looked down and sure enough, there was a line of cum stretched between the tip of my dick and the surface of the water. To my shock, Ric said " yum! " as he reached down and scooped it onto his finger then stuck it into my mouth to suck it off his finger. My dick bobbed from excitement and the guys voice their approval of the little show. A minute later Tim reached down and caught another drop then lifted it to my lips. I was surprised myself when I let him slide his finger into my mouth. 

Then it became a game. Ric reached down and grabbed my dick to milk out more, saying: "..someone catch it ..don't let it go to waste!" and they made a game of taking turns feeding me my precum. Ric's with one arm around my neck and the other hand slow milking my dick was keeping the pre cum flowing ....and the guys got into feeding it to me. The milking slowly picked up speed until my breath started to get faster and my eyes were starting to roll back in my head. Tim was quietly creating a porn soundtrack by saying  "...fuck yeah..that's so fucking hot. cum for us...let us see your cum face..." and on and on. My inhibitions were lower with all the beer we had that day and the next thing I knew I was approaching the point of no return. My stomach muscles were flexed and my knees were shaking. My hips were rolling in time with Ric's tugs on my dick and the guys were continuing to grab the pre cum and finger my mouth with it. 

I felt the electricity of an orgasm start at the base of my spine and arched my back trying not to cum. Ric quickly let go of my dick and moved my hand to take over. I was in the haze of pre-orgasm and instinctually took over pounding my dick. But now faster, just the way I like, rubbing and twisting over the head with each stroke. Ric moved behind me and latched onto both my nipples from behind to tug on them. I threw my head back on his shoulder and started beating my dick frantically. I could feel my balls pulled up tight as the water lapped against them. I grunted loud as the first blast of cym rocketed out of my dick. I heard a new voice say " what do we have here! " and my head snapped forward to see two new guys wading up to us as the next cum rocket left my dick. I locked eyes with the new guy as spurt after spurt left my dick. 

With each blast, my strokes slowed until I was slowly milking out the last drops. Finally was just left holding my dick in one hand and my beer in the other as the crowd of guys looked at me. Slowly the orgasm faded and post-nut clarity started to sink in, causing a new level of embarrassment. They were all grinning ear to ear as Tim said .." let's get some more beers.." then turned toward the beach with everyone starting to follow. Suddenly I was exposed to the beach. Ric whipped his baseball hat off and covered my dick with it. I grabbed it and tried to get my still-hard dick and balls covered as Ric took off to the beach as well. 

I rushed after them barely covering my dick and balls. I rushed back to our towels mid-beach giving everyone a clear view of my ass on the way. I finally made it and got my towel around my waist when Ric sat down beside me on our blanket. The other guys had wandered off down the beach leaving us alone. I told Ric I was going to fucking kill him, but he just laughed. He knew I enjoyed it.

After this adventure, Ric continued to push my boundaries of public nudity and embarrassing situations. His big turn-on was to get me naked someone and then jerk me off til I came. Sometimes it would be just us, sometimes he liked other guys to watch and join in teasing me. Every time I acted like I was shocked, but it was a game we played. The shock may not have been real, but the embarrassment I after I nutted was always genuine.

I lived in Chicago for a few more years with Ric. Our little adventure was a weekly occurrence and we got pretty bold. We could be just walking back to our car after going to a bar and he would pull me into a dark alley, strip me naked, and make me jerk off for him to get my clothes back. Or he would invite guys over to our apartment off Scruff. He would pick guys based on their desire to stay fully clothed while I stood in the middle of the room facing them and jerked off. At first, it was hot guys and I would cum pretty quick. Then he would start inviting over guys I wasn't necessarily attracted to and it would take me longer to nut and I would be even more embarrassed afterward. Then he pushed it further by inviting couples, then three or four guys. 

Eventually, I was more the party favor. We would be out at a bar and he would invite guys to come home with us to watch the "jerk off show". They would never get naked and he never let guys touch me. He made sure I only came if I did it myself. Towards the end, he started to experiment with dildos. He would secretly bring one out with us and then when he pulled me into an alley he would not only make me jerk off, but he would have me lean against a wall, car, or dumpster while he dildoed me. He would fuck my hole and I would jerk off until I came for him.

Eventually, I got a new job and moved to Fort Lauderdale and he stayed in Chicago. At first, he would fly down every few months and we would relive some of our fun. But as time went on we drifted apart.

Living in Fort Lauderdale was great because it was an easy trip down to Key West. I would go down three or four weekends a month and stay at different clothing-optional guesthouses. It was a rotating crowd of guys from all over the world coming to Key West to be slutty for a weekend. I had no trouble finding guys that wanted to play into my kinks and even explored a few new ones.

One of my early trips to Key West will forever be stuck in my mind because I still fantasize about it occasionally. I was dipping my toe into bondage and CBT. Nothing too extreme, just being tied up and jerked off or using ball stretchers during sex. On that trip, I had brought a new ball stretcher that had just come in the mail. Up to that point, I always used a rubber or silicone ball stretcher, so if things got too intense I could just slip it off. This new toy, however, was made from two solid pieces of metal that were attached by actual bolt screws. You even needed a special little tool to get it on and off.

I was staying at resort called Island House which was about a 15 minute walk to the gay bars located on Duval street. The first night I went out on that trip I decided to wear the new ball stretcher. It took some work to get into it, but eventually I had it locked on and then I got dressed in some loose cargo shorts, flip flops and a tanktop. I put the little wrench tool in my pocket with my id and credit card, just in case it got uncomfortable and I needed to get it off. Each night they have a happy hour around the pool to meet other guests and I always hit that for the free drinks before heading to the bars. I met this fun that evening that was visiting from Germany. They looked like two sterotypical leather daddys that had stepped right out of a porn. Both were super muscular, furry and flirty as hell. 

Our flirty happy hour conversation turned sexual in no time and I shared that I was trying a new ball stretcher that night. They of course wanted to see the toy in question, and after a couple cocktails we wandered to the far end of the pool with my back to the crowd and I unzipped my shorts and pulled my dick and balls out to show off the new toy. The attention had given me a semi-hardon. The took the opportunity to grab my dick and move it to the side to 'inspect' it closer. Really it was just an excuse to hold my dick and play with it until I was super hard. After some more flirting they invited me to join them for drinks at the bars. I put my dick away and we headed out for the walk to the bars. It was getting dark at this point and the gay bars were starting to come alive. My favorite place is called Bourbon Street Pub, because the back patio bar is men only and there is super hot bartender that always works that bar. 

We did our bar hopping that night and eventually ended up back at the resort. When we got back we just stripped down, threw our clothes on a patio chair and got in the pool naked. We swam and groped and played until it was super late. They invited me back their room, but I nicely declined, thanked them for the fun night and headed back to my room to get some rest. 

When I got back to my room, to shower and get ready for bed, I discovered that sometime in the evening the tool to get my ball stretecher off must have fallen out of my pocket. I went into a bit of panic mode. I raced back out to the pool to look around where we threw our clothes, with no luck. I knew the bars were closing so I went back to my room. I ended up showering and then sleeping in it that night. The next moring I was having breakfast when the German couple joined me. I told them what happened and they offered to help me retrace our steps to try to find the tool. By late afternoon I was really starting to panic, becuase there was no way to get it off without that special tool and I was really hoping I could order a new one. 

As we were walking back to the resort, one of the guys had the idea of visiting the local leather shop to see if they sold the same style stretcher. It was a great idea and we headed to Leather Master Key West. There was a handsome guy working behind the counter and I quietly explained to him what had happened. He said it wasn't the first time something like this has happened, and he would try to help me out. The store is small so he came around the counter and asked me to give him a look at the style. I dropped my shorts and he knelt down in front of me to take a look. My balls were red from wearing it all night and my semi-hardon had not gone away since last night. He had to move my dick around to try to get a look at all sides and figure out how it was locked on. After a few tries he stood up and said he needed to get better access. Without even asking, he grabbed me under the arms and sat my bare ass up on the counter, and told me to lean back on my elbows. Desperate to get it off, I did as he asked. He slid my shorts off over my tennis shoes leaving me naked except my shoes and tank top. Next he lifted my feet up on at a time onto the counter and asked me to spread my knees so get could get a good look at the screws holding it together. In hindsight, I'm not sure it was necessary, but he said he still couldn't quite see and he asked the German couple to stand on either side and then he pushed my knees to my chest and had them each hold a foot in place. 

This new position not only put my dick and balls on display, but it also spread my asshole open right in this strangers face. The German couple was loving it and started talking about my tight pink hole. My face went bright red. One of them even reached over and started lightly tapping my exposed pucker to point out how tight it was and that made my dick go rock hard. The shop worker was loving it too. 

After some exploration, he said he thought he might have a tool in back to get it off and walked away into a back room. The German guys just held me in place on the counter, leaning back on my elbows, knees pushed to my chest with my hole now exposed to the store. I remember feeling the airconditioning on my exposed hole. I feltwave of shock shoot through me as the front door opened and a new couple walked in. With the counter right in front of the door, they were welcomed by the two burly Germans spread my hole for display and my cock laying flat and hard on my stomach. The shop worker must have heard the door because he popped his head out of the back room and said " hey ..come on in guys! We are just doing a little demo of a new ball stretcher. I was mortified as they walked up to get a closer look. It was an older couple that I had actually seen at the resort - and they were all grins at my situation.

The shop worker finally came back out with a bag of tools. He took his place between my legs and set the bag next to me on the counter. He reached inside and pulled out a small bottle of lube and my eyes went wide. Without pause he said " I'm going to need to lube you up so I can twist the ball stretcher and get to the screws. " with that he popped the lid and squirted lube all up and down my dick and balls. He sat the bottle down and basically started giving me a hand job working the lube over my dick and balls. He paused to squirt on more lube a few times before it was running onto my stomach and down the crack of my ass over my hole.

One of the new guys was more than happy to jump in and say " oh! it's going to get on your shirt, let me help..." he zipped around the counter behind me and pulled my tank top up over my head to expose my chest and then slipped the arms over my shoulders until it was hanging behind me. With that he returned to the font to get a better look. By this time the shop worker was really focused on lubing up my cock and balls and was pausing every few moments to twist the stretcher. The whole scene was crazy and I was sweating, heart pounding and starting to breath faster from the stimulation. I was snapped back to reality when one of the German guys pointed out the lube running over my hole. He reached up to wipe it away, but instead he just started rubbing in small circles over my hole, telling the other guys he would just massage it in so it didn't go to waste. The sensation made me groan and that got everyone going. 

The shop worker noticed how I was enjoying the attention on my hole and stopped what he was doing to say...:" maybe I can reccomed another toy while you are here...would you like that?" I could only focus on the hole massage and moaned "..sure ..uh ..ok " He stepped away and then came back with something in his hand. I heard a click and then buzzing sound before I felt a vibration replace the finger on my hole. This made a new moan leap from my throat. He took that as encouragement and started gently probing my hole with the vibrating probe. 

I was already so far gone that my head just fell back as I enjoyed the sensation. A few more squirts of lube and he was probing my hole a few inches deep and then all the way out each time. He started giving a demonstration to the other guys telling them how the vibration would help relax the muscle. His probing continued as he started to demonstrate how to aim for the prostate, then how to use different speeds and depths to work the whole muscle. Without missing a beat he reached into the bag with his free hand and pulled out a larger dildo. He kept his probing going while he asked one of the Germans to squirt some lube on the new toy. 

Next he started to explain, and then demonstrate, how you should gently start alternating the two toys to further loosen the muscle. He was pulling the probe all the way out an instantly pushing the fat head of the new dildo in a little bit, then deep with the probe, then stretch with the dildo head, then deep with the probe then deeper with the dildo ...and back and forth and back and forth until the dildo was also going a few inches deep each time but, stretching my hole wider.

He was a master at what he was doing and I was lost in the sensation when he said " here ..give it a try.." With that, one of the new guys reached up and took over the toys. The shop keeper just stepped back and started coaching over his shoulder. Telling him faster, deeper , slower , aim for the prostate...this went on and on until the stranger had the hang of it. He as getting creative and trying new things until his buddy stepped up and demanded a turn. He was not at skilled and the shop keeper had to work with him to refind the rhythm until I was moaning again. 

I was really getting into it when the Germans each decided they needed a turn as well. I laid there and gave myself over to the sensations. I was so horny that I was unapologetically grunting and moaning. They were even encouraging me to get into and tell them I liked it. I was so into it, I was shocked to feel my body start to tighten up and the first edge of the orgasm approach. This brought some instant clarity when I realized I was about to cum without event touching my dick.

The shop keeper got louder and was really coaching the German to work my hole as he noticed I was getting close. My eyes were locked on the guy working my hole. He was drinking in the look on my face. Over his shoulder I saw the shop workers face light up... It was like a idea hit him and he disappeared for only moment and then was back to take the Germans place. He took over the larger dildo and set the smaller probe on the counter. Then he reached up and pulled my dick forward so it was pointing straight up a the ceiling. He didn't stroke it, just held it in the upright position with one finger. It dawned on me what he was doing just as he asked one of the other guys to take over the dildo. 

The fucking continued as he made a show of lubing up a long skinny metal rod by rubbing it in the pool of lube on my stomach. Then he slowly positioned it over the hole of my dick. I felt the cold touch my piss slit and then watched in shock as he let the weight slide slowly deeper into my dick hole. Once it was an inch deep he started a slow fucking of my piss slit. The sensation was overwhelming. My asshole was taking a slow deep fucking with the dildo and now my dick hole was taking a slow fucking. The sensation was so foreign that it froze me on the edge of orgasm. It felt like I was riding the edge of a wave of electricity ...the one you feel right before you shoot a load...but it stretched on and on. Every muscle in my body was flexed and I was sweating and moaning with my mouth open. I watched as the shop keeper coached one of the other guys to step up and take over sounding my dick. Once he coached them into a rythym, he moved away once more and then returned with a larger dildo. I was panting and moaning with my mouth open when he raised the new larger dildo to my lips and applied a little pressure to tilt my head back. Then he kept the pressure on until my lips parted and I opened my mouth to take the dildo down my throat. 

Just like he did with my ass and dick, the fucking started slow and then got deeper and deeper until I was gagging with each slow deep thrust. 

I had a moment of clarity when I heard the front door open again and a group of voices come in. There was a commotion and next thing I know I was hearing a crowd of voices. I couldn't look up becuase of the throat fucking. It wasn't until I looked to the side that I saw the mirror on the wall and the crowd of guys now gathered around watching me get every hole fucked for a crowd of strangers. the gaging was making tears run down my face. Spit and drool was bubbling out of lips around the dildo.

The shop keeper passed off the throat dildo to a new guy and then took over my dick again. He removed the sound and started to jerk my dick in time with the other fucking. With the sound gone, I felt the orgasm rise again. This time there was no turning back. My body convulsed and I felt the first blast of cum leave my dick and then splash back down on my chest, neck and face. He quickly reached up and pulled the dildo out of my throat before the next blast. Then lifed my head up so I was looking into the faces of the crowd as the third blast left my dick. He held me there while he milked out load after load. The ass fucking never stopped. They kept working me as I squirmed - until finally my dick was shriveled and super sensitive. Only then did he stop jerking and let go. Then he reached over an pulled the dildo out of my ass. 

The sudden lack of stimulation was a slap in the face. Everyone was quiet as I laid there covered in cum and lube with all my holes worked over. He reached into the bag again and with a quick tap and twist at my balls the stretcher fell away into his hand. 

He was all smiles as fell back - exhausted and spent. I felt something cold touch my dick and slide over it. A second later I felt my balls gripped, pulled and followed by a snap should. I found the strength to raise my head to look, just as he finished securing a cock cage around my shrivled dick. My eyes got wide and he reached up, with the help of the Germans to bring me into a sitting position on the edge of the counter.

He looked me in the eyes and handed me the ball stretcher. Then said "we'll see you back here tomorrow at 3pm and I'll show you how to get that cock cage off". Then he turned to the guys and said " alright guys...next demo is tomorrow at 3pm..bring your friends!"

That is the end of part one...if you want to continue hearing more about this story, be sure to leave plenty of comments and tell me what turns you on the most!