My First Iss

It all started about 2 months ago when a new neighbor moved into the apartment next door to me. His name is Jason, he is very personable and just an all around amazing guy. He is 34, about 6'3" with black hair and blue eyes and we hit it off pretty much as soon as we met. We are both veterans and newly single and we both liked to watch sports on TV, but we don't always agree on which sport. My name is Marcus and I'm 28 and a little shy of 5'6" with blonde hair and blue eyes.

After he got moved in and unpacked he asked if I wanted to come over and watch the game and have a beer. I happily agreed and told him I would grab some snacks. As we watched the game we talked about everything, just getting to know each other better. We both talked about our impending divorces and about how we really didn't have many friends outside our marriages and I told him I was glad to now have someone to hang out with and he said he was too. We got to where we were over at one or the others place almost every night. This had been going on for about 3 weeks and then it happened.

Let me first say I had always considered myself a regular straight guy, been married had a couple kids, been in the military and all that but truthfully I had for a long time been curious but had never had the courage to act on anything nor did I know of anyone to act on it with. So as we are hanging out and drinking and talking one night Jason told me he had something that he felt like he should really tell me if we were going to be hanging out all the time. What I asked? He swallowed hard and said that one of the reasons his marriage had failed was because he hadn't been completely honest with his wife when they married and that he had known for quite some time that he liked guys instead of girls.

I kind of choked a little and just stared at him for a few seconds and then asked him if he was telling me he was gay. He said yea I guess I am. He went on to say I just didn't want you to think I was hiding something from you when it comes out because I have decided that I am coming out of the closet so to say and he laughed a little. I told him it was fine that it didn't really bother me if he were gay or not that I considered him a friend and was glad to know him. That's when he put his hand on my knee and said I'm glad you're alright with all of it but there's more I need to tell you. He said, Marcus I'm attracted to you but if you don't feel the same way I understand.

My heart was pounding in my chest, here was this extremely hot and very sexy guy telling me he is attracted to me and all the time his hand is on my knee. I was going through all kind of emotions and not really sure of what I should or even wanted to say. I was just staring at him open mouthed when I was about to tell him I think I'm attracted to you too, but he cut me off and started babbling something about he understood if I was freaked out by all he had said and that he didn't want to mess up our friendship or anything and he hoped I would still want to be his friend.

I smiled as I put my hand on top of his and I told him that even though I considered myself a straight guy that I had been curious for a very long time and that I was attracted to him too.

He laughed and pulled me to him and we hugged as he told me that he was very excited about what the future might hold for us. I nodded my head and whispered in his ear that I was excited about that too but that I was just really plain old excited right now. He sat back a little and as our eyes met he smiled and asked me if I was saying that I was turned on by him. I smiled as I took his hand in mine and placed it on my crotch and said, feel for yourself. He squeezed my hard on through my shorts and said well it appears that things are going a lot better than he had hoped.

As he squeezed my hard on, he leaned towards me and placed his lips on mine and kissed me. I was a little startled at first but I quickly began to reciprocate and we kissed very passionately. I moaned into his kiss as our tongues sought out the others. We shared a very deep sensual kiss and as we sat back and looked into each other eyes we just smiled. He spoke first and asked me what I was feeling. I told him that I was very turned on and that I wanted to explore it more with him. He said he was too but that he wanted to know what I thought I wanted to do.

I kind of laughed and told him I didn't really know. I guess I have been curious for some time about being with another man but you know I'm not really sure what that involves. I get really excited when I think about taking a cock in my mouth and sucking it. I want to make the guy feel good, to please him and to suck his hard cock feeling him in my mouth and hopefully having him cum in my mouth. I want to taste him and swallow his cum, feeling him in my mouth and my throat and finally in my tummy. As I said that I smiled and lightly bit my lower lip and opened my eyes wide looking for his approval. He smiled a knowing smile as he nodded his head and leaned over and kissed me again.

I moaned "oh my, I think I could really get used to this." He said he hoped so, that he enjoyed kissing me and seeing me light up when he looked into my eyes. With that I smiled as I kissed him, our mouths opening and our tongues dancing with each other as my arms wrapped around his neck and his hands moved from my waist up my sides and across my back and back to my hips. He had succeeded in making me feel desired by him and he told me that everything I said that I wanted to try, he would love to with me.

You would I asked?

He smiled and said I would sacrifice for you and suffer through and as he did I slapped his arm and called him a shit. He just kissed my eyelid and nose before moving to my mouth again. So you want to suck me off huh, what else do you want to do?

Oh I'm uh not sure how to say it but I think for the most part I would like to receive but that I'm not really interested in giving but I guess I would if you wanted me to. He took my hand in his as he spoke and said well it sounds like we might just be perfect for each other. I smiled as I kissed him lightly on the lips and said oh yea you think so too huh. He said yes, notwithstanding those fabulous kisses but what you desire is what is commonly referred to as a bottom or someone who prefers to receive and I, as luck would have it, am a top or someone who prefers to give. I quickly interrupt and said Jason that doesn't mean that I wouldn't be willing to be the top as you say if that's what you want. He says I know I'm sure you would do that if I asked you and truthfully I have bottomed before but it isn't something I enjoyed so unless you decide somewhere along the line that you just have to be the top then I am perfectly happy with that role and you can stay in your role as my perfect bottom as he pats my bottom.

Oh Jason you just know the right thing to say don't you I mumble as I move to his lips for another kiss. So baby now that we have defined ourselves and our roles would you allow me to fulfill my first fantasy I purr as I stroke his very hard cock through his shorts and then slipping my hand up one of the legs of his shorts and finding him without underwear I wrap my slender fingers around his cock and squeeze. As he kisses me, he moans and says he would love for me to take his cock into my warm wet mouth. I purr baby I love the way you talk to me as he raises his hips up slightly allowing me to pull his shorts down and off past his feet. I take my place between his legs on the floor and as I look up into his beautiful eyes I smile and wrap my fingers around the base of his beautifully rigid cock and bring it up to my lips and then I run my tongue around the head and then from the tip down to the base and back up to the head. Not really knowing what to do, I try to do what I have had done to me that I enjoyed and some things I had seen in pornos. Always fantasizing it was me doing it to all the beautiful cocks in the films. He groans and begs me to take him in my mouth. He moans oh fuck Marcus please just put it in. I laugh as I smeared his precum along my lips and then push his cock through my lips and into my mouth gripping him ever so gently and making sure my teeth didn't scrape him. He brings his hands up to my head steadying me as I slide down onto his cock. All the way until his cockhead hits the back of my throat and I gag.

I pull back up and take him out of my mouth but continue stroking his cock as I look up into his face looking for some response, some help. I tear up a little and start to say I'm so sorry baby but he stops me and softly caresses my cheek and tells me its ok nobody gets it right the first time. He then tells me to relax and try again and if I gag again to pull back up and take a breath and try again. I smile up at him and move my mouth back to his cock and run my tongue all over the head. I slowly push him through my lips and into my mouth and begin moving his cock in and out of my mouth. I am so turned on at this point that I'm slobbering all over him and bobbing my head up and down in his lap and just working his cock over.

He continues to run his hands through my hair and stroke my cheek all the while telling me how great I'm doing. I so want to please Jason and start working my way down his length, I push him to the back of my throat and telling myself to relax my gag reflex and finally I push him past it and I feel his cock slide all the way into my throat. All the way until my nose is up against his pubic bone and I just hold him there. I loved having succeeded at taking him all the way in and deep throating his cock. As I hold him in my throat I have to swallow and when I do, Jason grabs a hold of my head and thrust his hips up and screams out loud "oh fuck, oh fuck" and I feel the first explosion of his cum down my throat. Just then I realize that I just sucked my first cock all the way to completion and making him cum made me feel so very sexy. I looked up and watched the expressions on Jason's face as he continued pumping his seed into my tummy and all I wanted to do was milk his cock.

I swallowed every drop of cum that came out of that beautiful specimen of man meat. As I began to slowly slide his cock out of my throat and then out of my mouth I look up into his face and tell him lovingly thank you so very much, I really loved sucking your cock. He pulled me up next to him and kissed me very passionately and told me how wonderful it felt for me to take him into my mouth and please him and that nobody had ever made him cum like that before. I swooned and told him that I would suck his cock anytime anywhere he desired and I would love to do it as much as he liked. He then asked if he could return the favor as he stroked my engorged cock, I pleaded with him that I needed a release but that he didn't have to. He took me in his mouth and slowly began to slide me in and out and I exploded. I told him I was sorry but I had just been so turned on for so long that I couldn't help myself. He brought his mouth to mine and as we kissed I found out that he hadn't swallowed my cum and it was then that he pushed it into my mouth. As we mingled my cum back and forth and kissed we collapsed together and fell asleep.

I woke first and as I lay beside him with my head on his chest I noticed his flaccid cock lying across his leg. I moved down to where it was and began licking his cock and then slipping him into my mouth. He awoke to his cock hardening in my mouth, I had long fantasized about waking a guy up by giving him head. He moaned oh yes what a way to wake up. As I spoke he pulled me up on top of him. As I laid on his chest looking down into his eyes he kissed me. So hot stuff did you have a nice little nap, I certainly hope you did because what's next is going to wear you out. I smile as I lie there and then I pull my legs down straddling him and sitting up I ask so what do you have in mind now? He moves his hands to my butt and squeezes and then while pulling my cheeks apart he moans baby I'm going to make love to you as he seeks out my tight hole with a finger and circles it.

I moan as he does and move into a kiss. As we kiss he continues to move his finger into me, slowly opening me up. Oh yes that feels good I mumble into our kiss. He moves me off him and lies me on my stomach with my ass sticking up in the air and continues his actions on my tight hole. He then moves down and starts licking my ass and tonguing me there. I squirm as he does and moan fuck Jason what are you doing. He tells me he is getting me ready for his cock, that it will hurt at first and that I need to be really worked up and overly lubricated. He then asks if I like the way it feels to have him tongue my ass I tell him I do and he goes back to work on me licking and tonguing my hole and starts working a finger into me. With his finger buried in me he began working another finger in and then a third. Now I was writhing and moaning in such pleasure I begged him to take me already, that I needed to feel his cock inside me.

He laughed a little as he moved up and straddled my ass. I could feel his hard cock sliding up against my butt and pressing in between my cheeks and pleaded with him. Oh Jason yes your cock feels so hard and so good against my skin. He said just wait until it's inside you. I moan then put it in me already. My my aren't you just the little slut he teased as he slides the tip of his cock up and down my slit. I push up against him trying with no luck to get him inside me. He laid down on my back kind of grinding his cock against my ass and while kissing my neck he whispers in my ear I hope you are ready for this. Just know I will go slow and I will stop anytime you want me to, all you have to do is tell me.

Nodding my head I tell him I understand and to please just fuck me already. He laughs and with that I feel him push the head of his cock up against my hole and then as the head of his cock stretches my outer ring and a lot of pressure and pain and plop and he's in. Oh I gasp, yes as he holds it there for a second and then continues pushing into me. Oh god Jason that hurts, but it feels so good too. Please don't stop please keep going just take it slow. He pushed his cock all the way into me, I couldn't believe I had all of his beautiful cock buried inside me but I could feel his balls resting against me so I knew he was.

He just held himself there pushing his cock inside me, it felt like he was in my stomach as I moaned and pushed my hips up into him. He kissed my neck and asked if I liked the way he felt in me. I told him no and then I groaned I love it. He began pulling his cock back and then pushing it back in and just then I knew I was getting fucked and I couldn't believe how I felt. It hurt, a lot but felt so incredible at the same time and every time he was all the way in he bumped something inside me that sent spasms through my whole body. As he moved in and out of me I just moaned and moved my hips pushing back trying to keep time with him. He stopped and pulled out until just the head remained and then pulled me up onto my knees and holding onto my hips he began thrusting again, I kept wondering how he knew this was my favorite position as I pushed back meeting his every thrust into me.

Sometime while he was pounding into my hot little ass I came. I hadn't noticed anything at first but eventually noticed cum leaking out of me and I didn't even have an erection. After a few minutes he stopped again and pulled out. He turned me around facing him and kissed me as he laid me down on my back and moved between my thighs spreading them open. I looked into his eyes as he slid into me once again, this time with almost no resistance. Once he was fully inside me he kissed me and told me he wanted to finish like this so he could look into my face as he made love to me. We kissed as he moved in and out of my boypussy; I call it that because like this that is the way it felt to me.

I moved my legs up and wrapped them around his waist, draping my calves across his sexy ass pulling him in deeper with each thrust. We continued for a few minutes more and he pushed all the way into me and I felt his cock twitch as he unloaded his hot cum inside my body. I held onto his shoulders with my hands and his waist with my legs as I felt his cum splash my insides. At that moment I felt like a woman who had just given herself to her man and I loved the way it felt, but I didn't understand it at least not yet.

Jason lifted his head and kissed me more passionately than I have ever been kissed and I kissed him back with the same fever. I moaned oh my Jason I loved that so much I don't want to ever let you out of me as I squeezed him with my thighs and with the muscles of my boypussy. He laughed a little and told me while he could not stay inside me all the time he would love to repeat this act as much as possible. As he said that I pouted and he said you even pout like a girl. I asked what he meant by that and he just motioned towards me on my back with him between my thighs. I laughed and said yea I guess it fits huh.

At home later as I lay there thinking about everything that happened tonight I found myself strangely a glow and wondering what this meant that I wanted. I found myself aroused again from the memories playing through my mind and while examining everything I came to the conclusion that I loved being made love to. Everything about being made love to, him sliding his engorged cock into my body, me taking his manhood into my tight passage and cradling him between my thighs and especially being kissed and kissing him back.

After playing the events over and over I felt my breathing quicken, my body spasm and twitch and I came without ever touching myself or even becoming erect. It was then I realized the other side of me was trying to break free and I think I wanted her to.

Since about the time I was 12, off and on, I have been crossdressing at least whenever I could find myself the necessary place and time. I was always curious what it would be like to be with a man while enfemme. I decided I was finally going to let someone meet her. Hopefully Jason wouldn't be totally turned off by her and even more so I hope that he would be turned on by her.

A couple nights later we were eating a bite and I said Jason can I asked you something. He said sure baby what is it? I told him I wasn't sure what I was feeling and wanted to get his take on it. He said go on. Well as we made love I was feeling very feminine and then I came from you being inside me without anyone ever touching me there and then when you made that comment about me even pouting like a girl, well I liked that you saw me as your girl in our relationship. Ok so what do you mean by everything? Well for some time now I have been crossdressing, I really enjoy wearing sexy clothing and looking and feeling sexy in it. So what are you saying to me, he asked? Well I guess I'm asking if you would be ok with me dressing while I'm with you. He told me if I wanted to he would be ok with it, he might even enjoy it too. I jumped up and into his arms and kissed him and said oh thank you thank you, I'll be back in a little while I'm going to go change and when you see me again I will be Alexis. He laughed and said I can't wait.

Back in my place I went to my closet and pulled out the outfit I had already decided to wear in case he said yes. It was a sexy red silk and lace bra, panty and garter set and I opted for some tan stockings. I decided on a sleeveless LBD or little black dress as it's called and a pair of red 5 inch stilettos. I had already shaved all the hair off my body so I slipped my toes into the stockings one at a time and slid them up my legs. I attached the garter belt around my waist and then each stocking to the straps hanging down. I stepped into my panties and then wiggled them up and over my hips and snuggled them into place between my cheeks. I fastened the bra around my chest and moved my breast under the cups, even though I don't fill them at all. Next I stepped into the dress and pulled it up over my shoulders and reached down the side and pulled the zipper up. I sat at my bathroom mirror and applied my makeup, a little foundation, black eye liner, black mascara, smokey gray and plum eye makeup, and finally bright red lipstick. I fitted a full blonde mane to my head and then stepped into my high heels. I wiggled around to my full length mirror and liked very much how Alexis looked tonight.