First time bisex for a friend while on the road

It was a late Wednesday evening Dave and I had been on the road driving for almost ten hours when we decided to stop and grab a hotel for the night. We stopped in a small town off Interstate 95 in Virginia and found a Hampton Inn off the exit. We had been driving a U-Haul truck from FSU in Tallahassee, Florida moving Dave’s daughter’s belongings. The trip had been long and we were both ready for a break from the road. We had both flown down on Saturday to get her packed and loaded and moved. Dave and his wife had been friends of my wife and I for close to twenty years so I was glad to offer my help when he told me about having to make the trip. The long ride in the U-Haul and my sore back had me reconsidering the intellect of my offer. As we checked-in the only rooms available were rooms with one King bed. Dave tried to find a room with two beds with no luck and finally settled on the room at the Hampton. I teased Dave that the next time he had a kid moving I would pitch in for two men and a Truck. We both laughed and walked across the parking lot to an O’Charley’s to get some dinner.

At dinner we laughed and joked about being too old to be doing the cross country U-Haul thing and I joked that we could have at least found a room with a hot tub for my sore muscles. Dave commented that he could not believe we could not find a hotel with two double beds and that he had never shared a bed with anyone but his wife since college. We had a couple of drinks after dinner and paid the check and left so we could get an early start in the morning and get on the road. We still had a lot of driving and we had to unload the truck when we got to her new place.

Back in the hotel we both took a shower and watched some TV before deciding to get into bed for the night. I took off my jeans, shirt and socks and pulled the covers down on one side of the bed and Dave asked “Are you going to sleep in your underwear?” I had not thought about bed attire and looked down. I love nice underwear and probably have a better assortment than most men. I was wearing a pair that I had ordered online that were basically a boxer brief that were tight and form fitting. They had sheer white panels and were a bright purple color. I normally slept nude so I had not really thought about what I was wearing until Dave mentioned it. As I searched for what I should reply Dave added “Wow, I have never seen a pair of underwear like those. Where did you get something like that?” I chuckled slightly and told him I loved the feel of nice underwear and liked to feel sexy so I bought them online. In my mind I was wondering how this was going to go. Up to this point in our relationship we had not ever talked about sexuality or seen each other in anything skimpier than bathing suits on one summer vacation we shared with the wives and kids. I could see Dave was intrigued and he gave me a quizzical look and asked “So, do you have more like that or are those for a special occasion?” I replied “Well, I usually sleep naked but all of my underwear are like these.” I grabbed my overnight bag and pulled it open and showed him a half dozen pairs that I had, all different and all sexy. I was not sure if it was Dave’s curiosity at the situation or if he was checking me out but I definitely could tell as I bent over to grab my bag from the floor that Dave was looking at my ass covered by the sheer ultra-revealing panel.

My fear of Dave’s reaction was quickly settled, Dave looked at every pair of my underwear and was full of questions. He asked how much a pack of these cost. I laughed and told him I have not bought a “pack” of underwear and that they are sold by the pair. I told him that they ranged in price from about $18.99 to $65.00 each and are all bought individually. Without a second thought Dave dropped his jeans and stood wearing a pair of saggy Hanes blue boxers. He exclaimed “These are less than ten dollars for a pack of six at WalMart!” Dave now stood in front of me talking about my underwear clad in a pair of saggy boxers complete with small holes from wear along with his oversized blue t-shirt and black socks. Dave was still looking at each pair of my underwear and I was looking at him. Dave was a handsome guy, about 5’11” with a little extra weight mostly in his belly and was probably 220. He had light blonde hair that was thin and always had a smile. I could not really tell anything about his anatomy with the boxers unlike mine that put everything on full display. I opened my laptop and brought up one of my favorite sites of men’s underwear and showed him some of the items on my “wish list”, again he seemed mesmerized. When I looked down I was surprised to see he had a boner tenting the front of his boxers. The fly opening on his boxers hung loosely open from them being so baggy and I could see the head of his cock barely visible. I could tell his hard on was not going away and we finally closed the lap top and climbed into separate sides of the bed. Silence filled the room as I pondered the events of the evening in my head.

I felt a hand move over and just barely graze my right side over my boxers. Dave quickly began to apologize when I stirred and he tried to cover what had happened “I didn’t mean to do that, I am so sorry I must have dozed off to sleep and been thinking about the feel of your underwear…….” As Dave continued to ramble on I didn’t reply but moved over closer to him in the bed to let him know it was ok. As Dave was still trying to explain himself away but digging a hole for himself I turned onto my left side away from him almost up against him and reached over taking his hand placing it on my right hip as I replied softly “It’s ok, you can touch as much as you like.” Dave became instantly quiet as his hand began to explore my ass solftly through my sheer panties. I could tell he was becoming more and more worked up and he began to talk again, “Your ass is so hot, I can’t believe this, I have never touched another man before or even thought about it…..” As Dave continued talking his hand became more exploratory not leaving any region of my bottom un touched. While he was still raging rock hard his hand touching my cock through my panties brought me to a state of being semi hard. This seemed to excite him even more. Dave now had both his hands roaming over my panties and was rubbing, kneading and caressing every inch of me. My cock was becoming increasingly excited and hard. I really never thought Dave would have any bisexual interests or feelings, this turn of events was totally a shock.

I felt Dave push his fingers inside the leg opening of my boxers and his forefinger pressed between my cheeks and began lightly flicking my anal opening. This excited me and I was instantly stretching the front panel of my boxers with my strained hard on. Instinctively I pushed my butt back to meet Dave’s fingers and in a shaky voice he said “I don’t know what to do, I have never touched another man before and don’t know how this is supposed to work.” His tone was apologetic and seemed to be asking permission at the same time. I replied “It’s ok, just do what comes natural and do what feels good. If there is something that I don’t like I will tell you. If you want something just tell me. Let is happen naturally.” Dave had his hands fully inside my underwear now and had me on my back. Laying on his side toward me he had his right hand underneath me as he played with my anal area and his left hand was inside the waistband of my underwear messaging my cock and balls. After a few minutes I reached over and pushed my hand easily inside the gapping waistband of Dave’s boxers and grasped his swollen cock. I could hear him gasp and lightly moan in pleasure from my touch. His cock was a nice size and I would guess about 5 to 5 ½” long and about as wide as my grip between my forefinger and thumb. He had a nice set of balls that seemed to hang low and full. Dave suddenly sat up and I felt his hands move to either side of my waistband and in one motion he pulled my underwear completely off me leaving me laying naked.

This was no longer about my panties. I could smell the scent of testosterone filled arousal in the room and Dave was fully into what was happening. I sat up and pulled Dave’s thick meaty cock from the waistband of his boxers and lowered myself and took him into my mouth. His cock was twitching and already oozing pre-cum and I pulled his boxers off his hips as I sucked him. Dave was moaning and uttering his pleasure as he raised his hips and used his hands to pull his boxers off his legs while telling me not to stop. His hands were on my head and he was using his hips to work his cock in and out of my mouth. The sensation must have been too much because it had only been less than two minutes when I felt Dave’s cock begin to explode in my mouth as his balls released torrents of cum hitting the back of my throat as I worked my best to swallow every shot and maintain suction on his cock. Dave probably woke everyone on the floor with his gasps, moans and sounds of orgasmic pleasure.

I was afraid that once he came that Dave would be ready to stop but his orgasm only seemed to fuel his drive. He was like a schoolboy on Christmas morning as he talked about how his wife did not like to give blowjobs and never swallowed for him and how incredibly hot that was. His cock was still rock hard and he pulled off his shirt and socks and started go down on me taking my cock into his mouth. It took him a minute of two to get going but once he did he was really into it. His saliva was running down my balls and down between the cheeks of my ass. As Dave continued to suck my cock I was getting close when I felt him insert his finger into my ass. This brought me over the top and I tried to tell him I was going to cum but he kept up his sucking and did not stop until I was fully drained and had to push him away because of the sensitivity of my cock. He was still rock hard and had his finger fully inserted in my ass which still felt amazing. As I tried to catch my breath Dave was talking and saying how hot that just was and how he had never done anything like this before.

Dave tried to take my semi hard cock back into his mouth and I told him we needed to wait a few minutes. Without stopping he moved down and with me on my back he pushed my legs up over my shoulders and using his saliva started playing with my ass and working more fingers inside of me. I love anal stimulation and having him finger fucking me was driving me wild as my cock sprang back to full hardness. I was lying enjoying the feeling as Dave was telling me how hot this was and how he never imagined anything like this. I heard Dave say “I want to fuck you so bad, I wish I could just take you and fuck you until we both cum together.” I was surprised and looked up at Dave kneeling between my legs and asked “What?” With two fingers impaled deeply inside of me Dave stopped suddenly and began to apologize saying he had just got caught up in the moment. I told him he did not need to be sorry and that I just had not heard him fully. He then repeated himself and tried to pass it off adding he knew it was silly and not possible. I was deeply intrigued and turned on and told him that it was possible but we needed to talk. I told him I had never done anything with anybody that I did not know very well without protection. He asked if I had ever done this before and I told him yes, I was bi. He seemed surprised and said he had never thought of anything like this or done anything with anyone other than his wife, Donna. I asked if they had ever been tested for any STD and he said no, that neither of them had ever been intimate with anyone else and that they only had sex once a month or once every six weeks. She had not allowed him to cum inside her for over five years saying it made her dirty and he had probably not had a blow job since his birthday several years ago until tonight.

We spent probably 20 minutes talking about our sex lives and I mentioned to Dave that I never thought anything like this would happen with his comments about “gay” and “bi” men. He said he just thought that was how men were supposed to feel and talk, he admitted to looking at other men and having a desire but never acted on any of it out of fear. I asked him if he ever had thoughts about me and he blushed deeply and said yes. He said he never would have acted on any of his feelings but when he saw me in my panties tonight he lost control.

I told him that if he wanted to fuck me we could do that. Dave asked “How does this work, I mean what do we do? I have imagined this in my mind many times but never thought anything like this would ever happen.” I was surprised to hear he had thoughts of this and told him again to just let things happen naturally. I told him that I needed to have plenty of lubrication and he needed to go slow. I told him I would tell him what to do when we got to that. Dave was seated in the bed and I lay down in front of him and told him to just play with my ass and to get me loosened up and relaxed.

Dave was an expert at playing with my ass and had me excited and relaxed in short time, my cock was rock hard and so was his. As I got into him fingering me and playing with my cheeks I told him to spank me. He gave me a soft swat and I told him I didn’t want it so hard that it caused a bruise but to spank me hard enough to make my ass red. I love the sensation of light pain and pleasure at the same time. Dave did a great job and soon my ass was stinging and I was moving away with each additional swat. Dave was so turned on he literally picked me up off the bed and put me down on my back as he pushed my legs up over my head revealing my vulnerable ass wide open to his sight and use. He was pushing his cock closer to me as he explained “god you have one incredibly hot ass” his words turned me on and I wanted to feel him inside me. Dave pushed the head of his cock inside me and I put my hand on his chest and told him to wait and let me get used to him inside me. It took a few moments for me to adjust and the initial feeling of pain allowing it to subside into a feeling of pleasure from the fullness. I moved my hands to his hips and pulled him closer to me saying “ok, now start slowly” as he pushed his cock fully inside me. I was afraid he was going to blow his load already before fucking me as he began telling me how tight my ass was and he had never felt anything that tight. It did not take him long before he started building up a rhythm and the sound of his body and balls slapping my ass filled the room. Dave had the perfect size cock for my ass.

Dave without pulling out of me asked if I wanted to try another position after about 5 or 6 minutes and I told him to do whatever he wanted to me. He pulled out and had me kneel on the edge of the bed and stood behind me and pushed back inside me and I told him “Dave, fuck me, fuck me hard” and he wasted no time before he was pounding my ass with a reckless abandon. My fears of him cumming too fast were soon lost as he continued this position for at least ten minutes. Dave changed position several more times and we were back with him doing me missionary with my legs pushed behind my shoulders when he told me he was going to cum and asked me where I wanted it. I asked him “where to do want to cum?” and he pushed deeply inside me fully and replied “can I please cum inside you?” I wrapped my legs around his waist and reached around grabbing his balls and told him “Dave, please cum inside me, I want your cum to fill me” I knew this would get him and it had the desire effect as he started to cum hard as he tried to get himself further inside me pushing me up into and against the head of the bed. Dave and I were both soaked with sweat from the intense fucking and both were breathing heavy. The sheets of the bed were in a ball and partially on the floor. Dave was spent and collapsed on top of me in total exhaustion. I was equally exhausted and without moving fell asleep with Dave still on top of me and his softening cock partially inside my ass that felt like it was on fire.

I could not believe when I woke up and Dave was still on top of me snoring. I turned my head to see it was 10:10 in the morning and we had planned on being up and out before 6am. I was lying in a puddle of cum that had leaked from me overnight and my cock was rock hard and aching. I could feel my ass had been fucked hard and was sore and aching in a good way. I shook Dave and he began to stir. As he woke up he looked at me and said “Oh shit, that wasn’t a dream was it?” I laughed and replied “Did you want it to be a dream?” He replied “No, that was the most incredible hot thing I have ever did in my life. I just don’t know where we go from here?” I teasingly replied “So, you still respect me in the morning?” Dave was very warm and was telling me how much he enjoyed everything and how hot he thought I was. He again asked “So, where do we go now?” I replied “Well, I still have a raging hard on I need to relieve and need a shower because we are already over four hours late getting started.” Dave rolled off me and said “I need to use the bathroom but come back to bed before we start getting ready to go. I have something I want to give you” We got up and used the bathroom and returned to bed. I was not sure what Dave had planned when he rolled toward me and said “Since I probably caused this, let me relieve this for you.” And he began sucking my cock and balls. I had lost my erection in the bathroom but as soon as I felt his touch I was instantly back. Dave worked my cock slow and firm not allowing me to get off very quickly. After about 30 minutes I was ready to erupt and the first shot of cum in the back of Dave’s throat made him cough and he used his hands to fondle my balls and jack me off as shot after shot of hot molten cum shot from my cock and onto my stomach, chest and face. I lay in the bed as Dave rubbed my body and my breathing slowed down and my heart slowed. Suddenly there was a knock at the door and a key card entered pushing the door of the room open against the hatch. A voice said “housekeeping” and Dave replied he had overslept and needed a shower.

It took us about an hour to get out of the room and back onto the road. Dave was excited talking about the events of the night and how much he enjoyed it. He said we could never tell anyone and I asked if he would tell Donna. He said no, never nobody could ever find out. He asked if I would tell Beth and I told him that we had no secrets and our sex lives were open. He could not believe my wife knew that I was bisexual and I told him she had known since shortly after we got married.

This happened five years ago and since this experience Dave and I have continued to play together. We schedule two separate long weekend trips together each year and it is always a lot of fun. Dave has never opened up about his bisexual desires and has not been intimate with any other men other than me. While at home our time and ability to play is limited but we still do have some time together and he says it is the hottest sex he has. Dave loves trying new things and always seems to have a list of things he wants to try when we do play. He sends me links to things online and always had a video he wants me to watch.