I have never been with man before this night. I had tried several times but never could find the courage. That is until I met Dan.
My name is Jim, 37, and I have never had sex with another man before but the idea had become more and more interesting the more I have thought about it. Being on and off and back on the dating apps, I never really got the courage to actually meet up with anyone. Until one night...
Dan and I had started talking through a popular app. It was all pretty casual at first. The normal stuff of getting to know each other; how old are you, what do you do for work, hobbies, etc. This was a pretty nice change of pace. Usually I would get on and guys would want to just jump straight into asking for pics and/or wanting to meet up. Sure, I have sent a few pics, it seemed harmless enough. But as I said I have never done anything with another man so meeting up was a bit too much for me. As time went on we began discussing more intimate things like what had we done sexually and what our fantasies were. I confessed to Dan that I had never been with a man before but was interested in trying it with the right person.
After about a month of talking Dan suggested that we meet up in person for drinks. By this point I felt very comfortable with him. He never pressured me into anything that I wasn't comfortable with and was a genuinely nice guy. So I agreed to meet him and local bar that I like to go to and felt safe at and we planned to meet that Friday night.
As the night drew closer I began to get nervous. I wasn't really sure why. I knew that Dan wasn't really expecting anything to happen, he even assured me that there were no expectations just some drinks and a good night out. But that didn't stop me from considering messaging him and not going. But I ignored my fears and after work I went home and got ready. I got a shower and dressed pretty casual; just my normal thong underwear, jeans, and a casual t-shirt.
when I got to the bar Dan was standing outside waiting for me as I was a few minutes late. he was taller than I expected. Being 6'0" my-self I was kind relieved he was a couple inches taller than me. He was dressed pretty casual as well with some loose fitting slacks and a short sleeve button down with the top two buttons open so a little chest hair was poking through. A bit more muscular than myself, enough you could tell he took good care of himself.
"Sorry I'm late." I told him.
"That's ok. For a second I thought you might have chickened out but I'm glad you made it!"
"Truth be told, the thought did cross my mind." I said with a nervous laugh.
"That's ok! The important thing is you made it."
It felt nice to be reassured like that. It really made me feel like he understood and made me feel safe with him.
We headed inside and grabbed a table that was near the back of the bar where it was a bit more quiet so that we could talk and not be disturbed. We sat down and got our first round. We talked for a while, just small talk at first. But as the rounds kept coming I started to feel more relaxed and the conversation got deeper and of a more sexual nature.
"What are some of your fantasies?" Dan asked.
"Well I have always wanted to be submissive. You know to be with someone that just takes charge and I'm helpless but to do what they say."
"That sounds exciting! anything else?"
"I would love to be tied up just used!" Did I really just say that?
"Oh wow you are more adventurous than I would have guessed!"
"I also would love being spit-roasted!!" I can't believe I just said that, maybe I should drink some water.
"I definitely never thought I'd hear you say that!"
"I know, it's the alcohol has gotten me all loosened up. Was that too much?"
Dan slid a little closer and put one arm around my should and placed his other hand on my inner thigh, "Not at all." His face was so close I could feel his breath on my face. He leaned in closer and kissed me softly. As I started to lean in to his kiss it became more vigorous. I parted my lips and his tongue snaked its way into my mouth. Our tongues wrestled and I could taste the mix of our saliva and alcohol. My cock began to twitch in my jeans as he began to rub my leg and our make out session continued. I reached over and felt his cock through his slacks. It was semi hard and already at least three inches longer than min, but that isn't saying much as I'm only about 3.5-4 inches hard.
Dan pulled back and a slight moan escaped my mouth. "Do you want to take this back to my place?" he asked.
I just gave a slight nod in agreement as I was still lightheaded from the makeout session. He stood up and took my hand and led me out. We had both had too much to drink to drive so we got a taxi and headed back to his place. On the way there the fun didn't stop. We began making out pretty heavy in the back seat of the taxi. Our hands were running all over each other, exploring every inch of each other. Normally I wouldn't be this adventurous in public. But the alcohol had lowered my inhibitions enough that I didn't care. Plus I trusted Dan and felt safe with him. The taxi driver was definitely getting quiet the show. I wouldn't have expected it but he kept peaking into the rearview mirror as if he was checking out what was going on. As we arrived and where getting out the taxi driver handed Dan his personal card and said anytime we needed a ride to give him a call and gave a wink as Dan closed the door.
As we got up to Dan's apartment and entered I noticed there were other pairs of shoes by the door that were a little too small to be Dans. "Whose shoes are these?" I asked him. "Those are my roommates. He is out right now and won't be back till late tonight. We should be all alone for a while."
"He won't mind that you brought a stranger home with you?"
"You are hardly a stranger. But no he won't, you could stay the night and he wouldn't care. He actually loves house guests."
"You think I'm staying the night? Isn't that a little presumptuous?" a little smirk ran across my face.
"Well after all we have had to drink it would be ungentlemanly of me to send you home in a taxi to take care of yourself."
"I definitely don't want to take care of my self." Now it was Dan's turn to smirk. "How about I put on some music and you can make yourself comfortable on the couch." I went over and sat down while Dan put on some soft background music he then offered me another drink. "I've already had a lot to drink but one more couldn't hurt." Dan went to the kitchen and came back shortly with a couple of beers. We sat for a few minutes and sipped our beers and talked. My head started to feel the effects of all the alcohol so I sat it down. "It's a good thing that I am staying the night. Can I use your restroom right quick?"
"Sure it's just down the hall."
I went down to the bathroom and closed the door. I just took a minute to splash some cold water on my face and get my head on straight. I looked at myself in the mirror in disbelief. Was this really happening? I was ready and I couldn't have picked someone better than Dan. I'm ready.
I went back out and sat next to Dan, our legs touching. We leaned in and began kissing slowly for a few minutes. It wasn't long before we were making out very heavy again, our hands moving over each others bodies. I just couldn't stop touching him, I couldn't get enough. I began to moan into his mouth as his hands reached my erect cock. He began slowly rubbing me through my jeans. Pulled back from the kiss just enough to say, "How about we take these off?" I leaned back and he unbuttoned my jeans. I lifted my butt off the couch so that he could slide them down and pull them off my ankle. I sat forward and took off my shirt. Looking at him I said,
"Your turn." He started by taking off his shirt and I motioned for him to stand up. I got on my knees in front of him. I could see the out line of his growing cock through the loos material of his pants. I slowly lowered his pants and to my surprise he wasn't wearing any underwear. Looking up I said, "You come prepared!" He smirked and me and I returned my gaze to his beautiful cock.
I reached forward and took hold of his cock in one hand and cupped his balls with the other. It was definitely bigger than mine. Not only a few inches longer but while mine was bout as big around as a had dog his about as thick as a good sized cucumber. I slowly worked my hand up and down the shaft, feeling every inch of it as it grew fully erect to a full seven inches. I leaned forward and licked the tip like a lollipop. It had a musky taste but not dirty. I slowly started to work the head into my mouth and he gently placed his hands on the back of my head. I was bobbing up and down his cock, getting it well coated in my saliva, all the while massaging his balls. It wasn't long before I could hear him beginning to moan and I could feel his hips thrusting back and forth, each time getting a bit deeper into my throat.
I started feeling him hitting the back of my throat and the taste of pre-cum started filling my mouth.
'That feels so good. I can't believe this is your first time." We continued like that for a few minutes when he suddenly stopped me. "If I don't stop you now I"m going to blow and we aren't near finished yet." I smiled as he took my hand and had me stand and he led me to the bedroom.
Once inside we began kissing as he guided me backwards toward the bed. He pushed me down on the bed which a little aggressive but I didn't mind. I was lost in everything that was going on. He got on top of me, one leg on either side and we began making out again. His hips began to move and I could feel his hard cock rubbing against my own. My thong was soaked through by our pre-cum.
"I think it's time for you to loose those." Dan started kissing down my neck to my chest, down to my stomach and then hooked his thumbs under the band of my underwear and pulled them down. My small, hard cock sprang out of them. I could feel my face turn red and closed my eyes and turned my face. Next to his my cock was an embarrassment. He saw my embarrassment and leaned down and kissed the tip of my cock. I was shocked and looked at him in surprise. "You have a marvelous cock." I smiled and we continued.
He lowered his head down and began working my cock with his mouth. Every time he would go down he would work his tongue around it. He had one hand massaging me chest and with the other he got a finger wet with saliva and slid it into my ass.
"Oh my god that feels amazing! Don't stop!!"
His sucking intensified and he worked two more fingers into my ass.
"Oh fuck, YES!! I love your fingers in my ass! I don't think I can last much longer!" Last I did not. With just a few more thrusts of his fingers I was ready to burst.
"IM CUMMING!!! AAAHHHH!!!" I blew my load in his mouth and he just held me in his mouth taking it all in. after my orgasm subsided he work his way back up me and kissed my, pushing my own cum back into my mouth. Not something I was expecting and a little aggressive but I loved the salty taste of my own cum, something I will definitely be trying again.
"Are you ready for the next part?"
"You bet I am!!!"
Dan stood me up and kissed me forcefully. "Turn around and get on the bed on your knees. Put your head down the bed so your ass is up." I did as I was told, this was exciting and getting me even more turned on. I had just told him earlier that I wanted to be a submissive and here he was starting to tell me what to do. He grabbed me by the hips and scooted me back so that my butt and feet were hanging off the edge of the bed. I was positioned just right for him. I felt something warm and wet on my ass hole. Then his hot breath made me realize it was his tongue. It felt amazing.
"HHHmmm."
"You like that?"
"I do, I really do."
"You are really going to like this next part."
he reached into the night stand and pulled out a bottle of lubricants. I felt the cool liquid hit the top of my ass and begin to trickle down my crack. He then took two fingers and got the wet and began working them in an out of my ass. I was in heaven. He pulled his fingers out leaving me wanting more. I heard a wet, rubbing sound and realized what came next. I felt his hand on the small of my back and with out warning he began to push his hard dick into my ass.
"AHHHH!!! Go slow, remember this is my first time."
"Just relax, it'll get easier. I already have the head inside."
I was a little shocked. His tone had change from the gentle and kind man I had been talking to for the last month to more authoritative. I had been excited by some of his forcefulness but I wasn't sure about this.
"I don't know it kinda hurts. Maybe take it out for a second and try again?"
"The only way is forward!"
With this words he gave another forceful shove and buried a few more inches inside me. "Ahhhh. Ow ow ow."
"Calm down, it's almost in."
Fear was starting to set in now, he wasn't listening and I wasn't strong enough to get him off of me. One final push and all seven inches were in. "OOOWWW!!!"
"It's in. I'll give you second to adjust."
Well at least he was giving me a second. It was really hurting when he pushed in initially but I had to admit the pain was starting to subside.
"Ok I'm going to start pulling out."
It began to burn a bit as he pulled out and push back in but the pain was starting to subside and even turn to pleasure as he started to build a slow rhythm.
"OOOwww, ooww, aaahhh, mmmhmmm."
"See it's better now isn't?"
"AAAHHH, yes."
He slowly was building up speed, my limp cock and balls swinging with each thrust. The pleasure continuing to build.
"AAAHHH, FUCK YESS! FUCK YES! FUCK MY ASS GOOD!!!"
"Who's my little cock slut?"
"I AM!!!"
"Do you love my cock in your ass?"
"Yes I really do."
"I can't hear you."
"AAAHHH. YES I LOVE YOUR COCK IN MY ASS!!!"
"That's a good cock slut."
The dirty talk was turning up my excitement to 11. My cock began to get hard again. I was loving every minute of this. Then he pulled out and my ass felt empty. "What are you doing?"
"Don't worry we aren't done yet. Turn over."
I rolled over onto my back. Dan picked up my legs and put one on each shoulder. Then with one big thrust he buried his seven inches into my ass.
"AAAHHHH! YES!!! OH MY GOD YES, FUCK MY ASS!!!! MAKE MY ASS YOURS!!!"
"This ass is mine from now on."
He Bengan to really pick up the pace now. Hammering into me like a jackhammer. Our skin slapping together so that other than our heavy breaths you could barely hear my moaning over the sound of skin slapping together.
My cock was rock hard again. With every thrust his dick was hitting my prostate sending a jolt of electricity through my body. I had heard of this sensation online but had never achieved it on my own. I felt like I was going to burst again.
He kept pumping into me for what seemed like forever but that was ok, I never wanted this to stop. But as all things do this had to come to an end. I began to feel that all to familiar feeling of my balls beginning to swell and I blew another load all over my stomach. As Dan kept thrusting he scooped up some of the cum on his finger and put it in my mouth.
"Now it's my turn. I'm about to cum."
Dan pulled out and told me to get on my knees. I obeyed his instruction while he began to jack himself off. He stuck the tip of his cock in my mouth and with a big grunt let his load loose in my mouth.
"Don't drop any. Just hold it in your mouth for a minute and then swallow."
I did as instructed. It is hard to believe but I think his cum tasted even better than my own.
After I had swallowed I reached for my clothes but he stopped me.
"What do you think you are doing?"
"I was going to get dressed and call a taxi."
"I don't think so. Remember? You are staying the night so I can take care of you in the morning. I'll also need some taking care of." A small smile spread across his face.
"Ohh ok. Yes sir."
"Now got up on the bed on all fours, I have a little present for you."
I did as he told me and he began to wipe my ass with a towel. Next he applied some lube to my ass whole again and I felt a slight pressure as he inserted a small butt plug into my ass.
"This way you will stay a bit more loose and it won't hurt so bad next time. From now on you will wear that before we meet up so you are ready for me."
"Yes sir." I was starting to really like this bossy side of him.
"Now let's get into bed and get some rest."
We got into bed where we spooned, his cock nestled nicely between my ass checks, were we fell asleep.