A Chance Encounter turns into a Week of Hot Fun

MONDAY NIGHT:

Day One

I was on the road traveling and decided after a stressful day to head down to the Hotel lobby bar for a drink. There was only a small group at the bar and all seated in various areas looking at laptops, phones or tablets. I took a stool at the bar with nobody close and ordered a drink.

The bartender was friendly and made small talk as he served me my Woodford Reserve with 7UP. After he walked away I sat alone watching CNN on one TV and reruns of a football game on another, neither of which really interested me. I decided to have a second drink and after the bartender brought me my glass I guy walked up beside me and asked if the stool was taken. I told him no and he sat and asked what I was drinking. I told him and he told the bartender he would have the same and to get me another. I thanked him and we talked about the weather and a few other general things. He then asked me if I was on the road a lot and I told him yes, I could tell he wanted to talk and I had not really had any company outside of work so asked him if he wanted to move to a table where we could talk more without the distractions of the TV’s. He smiled and said yes.

I learned Ted was 42 years old and lived in Tulsa. He had been on the road for the past two years and felt like he was in a mid life crisis of where to go or what to do next. We talked for about two more hours and the bartender made last call as the lobby bar closed at 9. Although I had already had six or seven drinks and felt a little buzz we each ordered two. The bartender said we were technically not allowed to carry them out of the bar but that if he didn’t see us there would be no problem. We both took this as his way of telling us he was ready to go and when our drinks arrived we both left and went up the elevator. We got out on my floor and stood in the hallway talking for another good twenty minutes and I finally asked him if he wanted to come finish his drink in my room. He said yes and we headed down the hall.

Inside my room I asked Ted if he minded if I took off my shoes and got a little more comfortable. He said no and I told him I rarely packed anything outside of my business attire since I was always alone and I slipped my shoes off and then took off my jacket, suit pants and dress shirt leaving only my boxer briefs. As I walked from the closet back to the study area where Ted was on the couch I asked again if he was sure I was not offending him and he replied no. I told him I left this morning at 5 to get into the office and had to shed the suit and relax. As I sat on the couch on the opposite end of Ted I noticed he was glancing at my boxers but not saying anything as he talked about growing up and such. Finally, out of nowhere Ted asked “So, have you ever had sex or anything with another man?” I thought for a second and answered “Yes, I have been with several men over the years.” Ted smiled and blushed a little as he fumbled with his drink. After a minute of silence I asked “Have you ever had sex or played with another man?”

Ted took a moment to answer but finally replied “No, but I have thought about it a lot, about what it’s like and all.” He paused momentarily to look to see my response and then continued “I would not know what to do or what it was like or how to start….”

I could tell he was stumbling and I interrupted “I guess it all depends upon who it is with and your feelings but I have really enjoyed the relationships I have had.” Ted was still sitting processing my reply and I asked him “Do you want to take off your suit and relax a little more?”

Ted immediately replied “If it’s aright with you…” pausing.

I replied back still sitting “It’s fine with me, whatever your comfortable with. It’s up to you.”

Ted said “ok” and got up and walked over to the bed and sat removing his shoes. He stood up and took his jacket off and then began unfastening his shirt after removing his tie. Ted was about 6’ tall and in decent shape. He did not have much hair on his chest and after lying his shirt on the bed he stood for a few moments and asked “Are you sure it’s alright for me to take off my pants or is that weird?” Ted stood fumbling with his belt clasp.

I replied “Ted you can go naked if you want, whatever you are most comfortable with is fine with me.”

Ted unfastened his belt and then pulled his pants off his hips. He did not have much body hair on his legs and was now standing blushing slightly wearing a pair of red bikini briefs. He walked over and sat on the couch saying he wished we had ordered another drink. I laughed and asked if he was comfortable. We sat for another fifteen minutes making small talk and I could definitely tell Ted had a semi erect hard-on that he continually tried to adjust and hide.

I looked at Ted and just asked him “Would you be more comfortable with taking those off?” gesturing towards his waist.

Ted replied almost immediately saying “I haven’t been naked around another man for a long time. Are you going to take yours off too?”

I told him that would be fine and I stood and pushed my boxers off my hips letting them fall to the floor allowing my semi rigid cock to spring forward in Ted’s fixed gaze. Ted then raised his hips and pushed his bikini bottoms off letting them rest around his ankles.

Ted had a nice cock at about 7” long and he was fully hard. His pubic hair was sparse. I grabbed two hand towels and handed him one as I laid the other on the couch to sit on. Ted adjusted his towel underneath himself and sat down talking fast. I told him to slow down and just relax, sit and take it easy. He asked what we were going to do next and I told him to just sit and relax.

Ted asked “Can I touch it?” as he reached his hand toward my waist line sitting next to me.

“Sure, you can touch and do what you like with it.” I replied as I sat back slightly.

Ted ran his hand over my cock several times and then began cupping my balls which made my cock leap to full attention. Ted looked up at me and said “I want to try to suck it, is that ok?”

I told Ted he could just move slowly at his own pace. Before I could get the words out of my mouth Ted had my cock inside his mouth as he knelt between my legs on the couch. It felt good but after about a minute Ted got up and said “I just can’t do this” as he started to grab his clothes and he was out of the room within two minutes.

I was turned on and still had a hard-on and jacked off and then went to bed for the night.

TUESDAY:

Day Two

Tuesday was another long day at the office and I was just looking forward to getting back to my room and relaxing. I arrived back to the hotel late around 8:30 and noticed a voicemail on my phone so called the front desk and got my voicemail code to retrieve it.

I had four new messages all from Ted. He wanted me to call him when I got in and said he was really sorry about the night before and tried to explain his reaction. I was on his third message when there was a knock at the door and I hung up and answered to find Ted outside with several bags. Ted began to apologize again and I quickly invited him inside to ensure we did not cause a scene in the hallway. Ted had brought food and drinks and said he was just so incredibly turned on last night and did not know how to process all his feelings. I finally told him it was fine and offered him to sit down. I told Ted Ihad just walked in the door from work and needed to get comfortable so I went into the bedroom and undressed and came back into the sitting area naked with my towel to sit on. Ted was looking at me strangely and I told him I was usually nude in my room. His only reply was an “Oh”.

Ted poured us both a drink and then followed suit and took his clothes off as well and came in and sat next to me naked and fully hard again. Ted looked at me and at my limp cock and then asked “Did I do something wrong?”

I told him “No, I just am not aroused at this point but it is nothing on your part.” Ted smiled and continued talking before suddenly reaching and grasping my cock and leaning over taking me into his warm wet mouth fully. Ted’s mouth felt amazing on my cock and I was growing to full erect quickly as I started moaning in pleasure. I was surprised Ted did not let up or slow down. For his first time giving a man a blowjob he was doing a great job. He continued for about ten minutes before I stopped him as I could feel myself getting closer to orgasm.

I told Ted to sit beside me on the couch and I grasped his rock hard cock and began to jack him off with my hand. Without having to direct him he grasped my cock and began to repeat my actions. After about five minutes I shot my first stream of cum  up over my belly and chest and Ted quickly took his hand off my cock. I told him to keep going and he started back again as I shot jet after jet of hot cum covering my chest and stomach. I was midway through my orgasm with my eyes closed when I heard Ted groan he was going to cum and I felt his cock twitch in my hand. I continued jacking him and felt his cum on my hand as he shot his first load all the way up onto his face followed by a river shot onto his chest and stomach.

Once we were both finished we both were sitting back on the couch breathing heavily with each other’s cum covered hands still on the others cock. Ted broke the silence after a moment “That was amazing.”

I replied “That was hot, are you ok with everything that happened?”

“Yeah, I really enjoyed it. It was really weird at first knowing I had another man’s cock in my mouth but really after the first minute I just was really so into it I didn’t even think about it.” Ted said still holding my soft cock. He continued “I was so nervous after last night but it’s all I could think about all night and all day today. I spent hours watching guys on my phone and looking up how to give a guy a blowjob. I hope I did ok.”

I laughed and told him “You did an amazing job, you’re a natural.”

We cleaned up and then sat naked on the couch until 11:45 and I told Ted I had to be out early and asked if he would be in town again tomorrow evening. He said yes and he did not fly out until Friday afternoon. We exchanged numbers and I told him we should have dinner tomorrow and he said he would like that. He grabbed his clothes and left.

WEDNESDAY

Day Three

It was about 4:00 Wednesday afternoon when I received a text from Ted asking if I wanted to meet him at a local sushi restaurant near the hotel at 5:30 I replied and told him that sounded great and to meet me in the bar as I was in a meeting until 5 and had a few things to finish up and may be running a minute or two late.

It was almost 6 when I arrived and found Ted sitting at the bar. I apologized for my lateness and we went into the restaurant area with our drinks and enjoyed dinner. Ted seemed happy and excited although we did not mention the events of the previous night. I could tell this new experience had him wound up. After dinner we agreed to meet back in my room for a nightcap and we left the restaurant.

I arrived back to my room and changed staying in my undershorts as I waited on Ted sitting at the desk on my laptop trying to respond to several emails. About twenty minutes later Ted arrived with a bottle of wine. I welcomed him inside and he immediately stripped out of his clothing completely and sat totally naked on the couch. His cock was already hard and he was talking about the night before and how hot he thought it was. He said he could not stop thinking about it all day. He said he had never really gone naked even at home alone and that sitting in a room close to another man while being fully naked was such a turn on for him. I poured our second glass of wine and as I handed it to Ted before sitting down Ted grasped my waistband and pushed my undershorts off my hips letting them fall to the floor at my feet. I moved and sat on the couch to continue our conversation.

Ted was talking a mile a minute as I leaned over and took his cock into my mouth. He was as hard as steel and as soon as I engulfed his rigid member his head leaned back and I heard him mutter “oh my god oh, oh, oh……” I felt his hands on the top of my head as I continued to suck and lick his entire shaft while using my hands to massage his balls. I could taste his precum and it only took about three minutes before I could feel his cock begin to twitch and spasm and his nuts drew up. I knew Ted was getting ready to cum and decided to keep going as I heard him utter “oh my god I’m going to cum” and he started shooting load after load into my mouth as I struggled to swallow all of it. After he stopped cumming I continued sucking him as I felt his cock begin to go soft until he finally tried pushing my head away telling me to stop because he was so sensitive. I sat back up and looked at Ted who still had his head leaned back and his eyes closed and asked “So, now what were you saying?”

Ted lifted his head and replied “I don’t remember but that was the most incredible orgasm I have ever had.” I rubbed his leg and he continued “I have never had a blowjob to the end like that. Thank you.”

I sat back and picked up my wine and took a sip. I was still rock hard myself and needing release. I felt Ted’s hand surround my shaft and begin to slowly jack me off before he moved down and took me into his mouth. I shifted my body down into a lying position on the couch and began to moan in pleasure which intensified Ted’s actions as I felt his saliva running down my balls and down my ass. I told him “stick your finger inside my ass” as he continued to suck me. I felt his finger toying at my anus and pushed my hips down to insert his finger inside me. It took him a few minutes of me moving my hips to grind on his finger before he started finger fucking me and added a second finger.

I reached over and felt Ted’s cock was again hard and I started to jack him off as he continued to suck me and finger fuck me. I finally after about 10 minutes began to cum and cold tell Ted was trying his best to swallow my load. As he tasted my cum his own cock again exploded and I could feel his cum hitting my side. As I finished cumming Ted stood up and looked at me with his face covered in cum and cum running down his chin that he had lost while sucking. He still had two fingers pushed fully inside me and started to pull out as I told him to pull out slowly. I sat up as I recovered once Ted’s fingers were removed and said “wow”.

Ted sat on the couch and said “That was the hottest thing I have ever done.” He wiped his face and we both took a sip of the last of the bottle of wine.

We sat talking for another hour and decided we both needed to get to bed with both having an early day in the morning. It was already after 11. Ted asked if I wanted to get together tomorrow and I told him yes. We agreed to meet in the lobby bar at 7 the next day and Ted got dressed and left. I turned the lights out and went to bed still naked and satisfied falling asleep quickly.

THURSDAY

Day Four

I was already sitting in the bar with my drink as Ted walked in Thursday evening. We exchanged greetings and Ted sat and ordered a scotch on the rocks. I remarked that was a great choice and motioned for the bartender to make the same for me.

After three drinks I was feeling tipsy and told Ted I had probably had enough since I had to be out early and check out in the morning before heading to the office for the day. He agreed and said he had to be out and in the office by 8 the next morning as well. We paid our tab and went upstairs. Without even talking about it we both proceeded to my room and once inside both stripped out of our clothes while making small talk about the day and our travel plans for the following week.

We sat on the couch naked together for about an hour with nothing happening but we were both semi hard the whole time. We had a great conversation and Ted finally changed the subject and asked “Last night you wanted me to stick a finger in your ass, do you like that?”

I replied “Yes, I have always enjoyed having my ass played with and penetrated. For me it really enhances my orgasm and feels amazing.”

Ted sat for a moment and then said “I have never done anything like that, I don’t think I would like anything like that but it was very erotic and hot to have my fingers inside you and I could tell you were really enjoying it. Have you ever had a man’s cock inside your ass and let him fuck you?”

“Yes, if I really trust somebody it can be very hot and enjoyable for both of us.” I replied. After a pause and seeing Ted contemplate the response I added “Would you like to play with my ass tonight?”

Ted looked quizzical and as he lightly stroked his own hard cock said “I really don’t know what to do, this is all very new to me.”

I moved closer to Ted and helped him lightly stroke his cock “There really isn’t anything specific, just rub my cheeks, you can playfully spank me and tease around my anus with your finger if you want. You can lick me and play with me orally or do whatever you think feels good and gets you hot.”

“I don’t want to do anything that hurts you” Ted said.

“Don’t worry about that, just do what you like and if I don’t like something I will tell you or if there is something I want you to do I will let you know.”

We got up and walked into the area of the room where the bed was and I pulled the covers down. I laid on the bed on my stomach and Ted put his hand on my ass. He paused for a moment talking briefly and started to rub me. I felt him begin to massage my cheeks with a little more effort before he was pulling my cheeks apart and looking at my anus and telling me what a hot ass I had and how much he liked it. He began rubbing my anus with his forefinger and it felt great until he tried pushing his finger inside me. I jumped a little and said “Ouch, we need a little lubricant to do that.”

Ted back off and apologized and I told him it was fine just to get me lubricated like last night before pushing anything inside me. He rubbed me for a few more minutes and then I felt the heat of his breath between my cheeks as he began playfully licking me. As Ted began to rim my ass I quietly told him to slap my ass cheeks. Soon Ted had me moaning loudly in pleasure as he rimmed my ass and alternated fingering me while occasionally slapping my ass with a stinging swat. What he was doing felt amazing and I wanted more as I asked him “What do you want to do?”

Ted continued finger fucking me with two fingers and playfully spanking me as I heard him say in a deep voice “I want to fuck your ass.”

I moaned in ecstasy saying “I want you to fuck me, Ted.” I could feel Ted begin to push his cock between my cheeks as he spread me open with his hands and I told him to wait and let me move. I turned over onto my back and as Ted knelt in front of me I raised my hips and placed my legs on either side of his head resting them on his shoulders. I was looking directly into his eyes and told him “Go slow and make sure I am wet.”

I told Ted I had a small bottle of lube in my nightstand and he grabbed it and lubed himself up and then applied some to my ass and fingering me. I was ready to feel him inside me and told him “Fuck me Ted, please fuck me.” This put him over the top and he grabbed my ankles and pushed my legs up over my shoulders and started to enter me.

I felt a bolt of pain as my ass was invaded and cried out “go slow, let me adjust” and Ted slowed down. As I got comfortable I told him to continue until he was fully inside me and started to fuck me. Once I was used to his cock I was telling him “Fuck me hard, Ted.”

Ted fucked me for about five minutes and then told me he was getting ready to cum. I wrapped my legs around his waist and pulled him into me as tightly as I could before he grunted and started to cum pushing himself deeply inside of me. I pulled his shoulders and embraced him and he began kissing my neck.

Once he was done Ted moved off me and then said “You didn’t cum, I wanted to get you off too.”  He began jerking my dick and then went down on me.

I told Ted I wanted him to lay next to me and to hold me tight. He took my cock from his mouth and asked if I didn’t want to get off and I told him I did but I wanted him to hold me now. Ted moved beside me and gave me a bear hug from behind. I could feel his cock stiffening as I ground my ass cheeks into him. As his cock grew Ted was kissing my neck and back and told me “I want to fuck your ass again.”

I replied “I want you to fuck me again.” And felt Ted stick the head of his cock into my cum leaking messy ass as he grasped my cock and started to jack me off as he fucked me slowly. The feeling was amazing and I lay enjoying the sensations for about ten minutes or longer before I started to cum. My body was tightening up and shaking with my pent up orgasm and this took Ted over the top again and he held me around my waist tightly and emptied his second orgasm inside me.

Once he had finished we both lay panting catching our breath and with Ted’s cock still buried inside me he pulled the covers up over us and held me tight.

I awoke to my alarm at 5:15 the next morning and could see daylight through the curtains. Ted was still holding me and his cock was hard once again and still inside me as he was holding my hard cock in his hand. I did not want to move and felt Ted begin to stir. My alarm went off for three minutes and then reset to a 10-minute snooze. My stomach was bloated with air and cum as Ted’s hips began moving driving his cock in and out of me slightly. My alarm went off again and this time I reached over to turn it off. My movement caused Ted’s cock to pull out of me.

We both got up with a raging hard-on and I asked him if he enjoyed himself last night. He said it was the best night of his life and thanked me several times. We both got into the shower together and got each other off again before Ted got out and got dressed to go to his room.

After he left I showered and shaved and got myself packed up. I left the hotel and checked out without seeing Ted again that morning. He sent a text while I was at the airport thanking me for a great week. We have stayed in contact and plan to meet up again soon.