Twenty one years of of bisexual exploration

Sex, drugs and hotel suites

In the course of the year since my previous encounter with the dominant bear not only did my cross dressing evolve but my marriage dissolved for unrelated reasons. It had been 4: years since my wife and I were intimate and despite my trying she had consistently rejected me, which seemed to be a big driver in my bi exploration. It was almost a relief when she asked for the divorce. 

We separated but she stayed in the house, moving to a guest room. Immediately she had a boyfriend that she pretended didn't exist. I started hanging out with the party girl I had an affair with a few years earlier just to get away from the house and have a shoulder to lean on. I stopped cross dressing, and fell into a bit of a depression. For the first time I was free to explore and my desires had dried up. I just wanted to escape and I was offered a way to do so. It wasn't my finest hour of decision making but when I discovered my female friend was using heroin I made her share.

I'll point out that this was a ridiculous choice, I was a professional in my late 30s, I worked in pharmaceuticals and I know all the risks. She wanted to limit me to snorting but I was so self destructive I insisted on shooting it by the second time. I managed to keep it casual until my wife finally moved out, after that it was a "managed habit". It was after my next encounter on a business trip that I insisted she find an apartment.

Work had taken me to a medium sized Pennsylvania city. It was almost a 5 hour drive but I insisted on not flying so I could bring weed and dope with me for the long nights alone at the hotel.

The company put me up in an extended stay suite in an area occupied with hotels. As soon as I checked in the urge hit me and I downloaded Scruff again and logged into my profile. I made myself a quick dinner in the small kitchen and scrolled through profiles as I ate. I favorites a few guys who seemed like they might be my type and then after I ate, I got high. I had arrived late and had an early first day the next day so I jerked off and went to bed.

The next day was an extremely boring day of getting acquainted with my team and the project I was hired to manage and all I could think about was Scruff. 

I checked every chance I got to see if I had any messages but when I did the guys wanted to meet right then. "I need to get back to the hotel" I kept thinking. Finally 5 o'clock came and I was headed to my new short term home.

I started making dinner for myself and opened Scruff as I cooked and to my surprise a hairy older man with a beard came up as closest to me, when I looked at the distance it was 300 feet, he was in the complex of hotels. I messaged him as I finished cooking and we started talking while I ate.He was gay, married and his partner was no longer sexual and like me he was trying to take advantage of his time away. Our conversation went for about an hour, he was sweet and attentive and I shared my last experience as a way to let him know what I wasn't looking for, he was appalled that someone would do that to me and he seemed genuine. Surprisingly we didn't share any photos, it was really all about attitude and we just seemed to click.

My heart started racing when he invited me to his room, I didn't even hesitate to say yes. I told him I needed 40 minutes to clean up dinner and wash up. I jumped in the shower, then got high and let him know I was on my way.Getting high did not cure my nerves but it did take my inhibitions and my mind was racing as I smoked a cigarette while walking across the parking lot to his hotel. He met me at the back door to the hotel "you're much more handsome than I imagined" he said as he introduced myself, I was honestly flattered and excited as he lead me to his room.

He was a big man, over 6 feet and brawny with a well groomed grey beard and hair. He was exactly my type.He complimented me again when we got into the room and asked if he could kiss me, I didn't answer, I just learned in and kissed him. His beard gave my lips that familiar tingle that one can only get from kissing a man. We kissed deep and passionately, he was an amazing kisser. I put my arms around his neck, he put his around my waist and we made out like teenagers for about five minutes until he started to pull up my shirt and then I pulled his off to reveal his manly, hairy barrel chest, I moaned and started kissing his neck and then reached down to feel his manhood.

We had only briefly talked about endowment and he had only said that he was "hung". When I grabbed his bulge through his loose gym shorts I was pleasantly surprised to feel a semi hard, thick, long cock. "Mmmm your cock feels so big" I moaned as I started to kiss my way down his hairy chest. "I said I was hung" he replied as I pulled his shorts down and freed his cock. I wrapped my hand around it as I kissed my way down his hairy torso until I was on my knees. I admired it as it continued to grow. 

I looked up at him and licked my lips then wrapped my lips around his big, swelling mushroom head and sliding half of him into my mouth, and taking more with each stroke of my head. After a few minutes he pulled me up to my feet and kissed me again, then reached down and unbuttoned my pants, then pulled them down as eagerly helped wiggle out of them "your pretty hung too" he said with a smile and grabbed my cock and kissing me again. My cock was rock hard and swollen from kissing and sucking him. 

We stroked each other for a minute as we kissed then I put a hand on his chest and gave him a gentle push to the bed, he got the hint and played on his back. "Mind if I vape while I suck that beautiful cock?" I asked. I had fantasized about giving a smoking blowjob for quite awhile and though he had a non smoking room I decided vaping would be a close second. "As long as it doesn't smell and get me in trouble" he responded. 

I grabbed my pants off the floor and pulled a disposable e-cigarette from my pocket, took a drag off it as I climbed into the bed between his legs and let the vapor cloud slowly pour over his now fully hard cock, which was at least 8 inches long and very thick, as I licked from his balls to his head then slide him back into my mouth. I slid him out and smiled at him "see, no smell" then slid up to kiss him "no taste either" and slid my tongue into his mouth. "Mmmm good, it's sexier than I expected". 

I kissed his body again as I moved down between his legs and took another pull on the e-cig and blowing a stream of "smoke" on the head of his cock and then working him into my mouth. He had the biggest cock I'd ever sucked to that point and with the help of my opiate and weed high I devoured it, thinking how much easier he was to work deep in my throat than the aggressive small cocked guy I had the previous year. 

I managed to take him deep, getting most of his cock deep in my throat only gagging occasionally. I worked his cock slow and deep in my mouth, moaning non stop each time I took more of him in my mouth, stopping occasionally to take a drag and tell him how happy I was to suck his cock. I licked and sucked his balls and passionately sucked his throbbing cock for about 20 minutes before his moaning got faster and louder, his balls started to tighten and I knew he was close "I'm going to cum soon" he moaned and I answered back "mmmm, good, I can't wait to taste your load in my mouth" then grabbed his hand and put it on the back of my head and started working him faster, tightening my lips and adding more suction. 

A few seconds later he held my head down and I felt his thick cock start to pulse as he started to erupt in my mouth. Rope after rope of his hot load filled my mouth, he hadn't cum in a week and his cum started to drip out of the corner of my mouth and he was still shooting thick, hot pulses of cum. I swallowed some to make room for the rest of his load and moaned, it was the hottest sexual experience and what I had been looking for since I started exploring men.

I slid him out of my mouth and looked up at him, watching him pant then showing him my mouthful of cum as he watched, then I giggled a slutty, satisfied giggle and licked the dripping cum from the head of his cock. He pulled me up for a kiss "that was so fucking good, you're a great cocksucker" I put my hand on his chest and kissed him deeply "well, it's easy when you have such a great cock" and then sucked his lip. 

He pushed me on my back and kissed me as he climbed on top of me and started making his way between my legs. Up until then I never really let a man suck me, I let the first guy suck me for a few seconds but then I stopped him. I don't know if it was being high, how much we clicked or a combination of both but I didn't even consider stopping him. I ran my hands through his short hair and moaned as I watched him consume my cock. 

I was so worked up from draining his balls that it only took a few minutes before I started to unleash my own orgasm, cumming in another man's mouth for the first time. Before he swallowed I pulled him up for a kiss, then we laid together and talked and kissed for awhile and made plans to see each other the next night after work and I went back to my suite after one last goodnight kiss.The next day I had to travel to another city about 60 miles away for some eetings at a second location and day dreamed about him the whole drive back to the hotel. 

He sent a message that he wouldn't be back until 6 so I got high and made  dinner and waited for his dot to come online. He  messaged me just before 6 and we chatted about the night before and how we both thought about it all day. I mentioned that I really wanted to go further and he said he really wanted to eat my ass. I told him I would be over around 7, I needed to clean up for him. I got high again and took a very good shower, making sure my ass was clean enough to eat. 

After my shower I decided to get high one more time so I'd be nice and relaxed for the cock I was hoping to take in my ass for the first time.I was feeling warm and fuzzy from the extra dose of dope and excited to see this man again and I felt like I floated across the parking lot as I smoked a cigarette and approached the back door. 

This time I just went up to his room and knocked.He opened the door and as soon as I was inside he pulled me in for a long kiss, I didn't waste time and was soon on my knees in front of the closet door full length mirror watching my self worship his beautiful, thick cock. I liked the way I looked sucking his cock like a slut, seeing myself high without my lover knowing being his whore. He took my hand and pulled me up to kiss me and take me to the bed. 

He laid me on my back and got between legs and lifted my legs and started teasing my ass with his tongue before centering in on my hole. I tossed my head back and let out a moan, reaching down to run my fingers through his hair, feeling his beard on my skin as he ate my ass. After a few minutes I was begging for him to let me suck his cock while he ate my ass and we soon switched positions after a long tangy kiss.

 I straddled his face and had full access to his cock and balls. We stayed in that position for at least half an hour, him eating my ass and fingering me as I moaned into his cock taking him as deep as I possibly could. Soon I was moaning "Daddy, I want you, I want you in me so bad" and he rolled me off him and I was hoping this meant I was finally have a man in my ass. Instead he started fingering me deep and massaging my prostate as he sucked my cock.I desperately tried to hold back my orgasm, but within a minute or 2 I was moaning that I was going to cum and I exploded in his mouth, cumming harder than I have ever cum. 

He crawled up and put his cock in my mouth as I laid there panting and I eagerly started to suck him, he pulled his cock out of my mouth and started jerking off while I lick at the air with my mouth wide open, waiting for my sticky sweet reward. He grunted and came into my open mouth and on my face then laid back on the bed, I of course leaned over and licked the last drops of his load from his cock and then kissed him. 

He wiped the cum off my face and I took his hand and sucked it from his fingers and then we shared a few minutes of sensual kissing. Then we got up to clean up and get dressed. We chatted for awhile and he told me he wanted to fuck me but felt like that would be going to far given his husband, but then said "fuck it, what are you doing tomorrow night?" and we made plans for another meeting but this time it would be a date, dinner, drinks at one of the gay bars and then back to the hotel. Unfortunately the next morning I had finished all onsite work early and the project director sent me back to check out and then he would have me work the next day remote from my home office, to save on travel expenses.

I sent him a message on Scruff as soon as I was back at the hotel packing up and let him know I was heading home a day early and I was bummed we wouldn't have a date night, he understood, but I still drove home feeling disapointed. I had such a good time with him and he was exactly who I wanted to lose my anal virginity to.My work on the project stayed mostly remote and I started getting romantic with my female friend and sexually she left me very satisfied. It would be a few more years and a move before I would have my desire for men lead me to more sexual adventures