My First Time .......With My Longtime Friend Jason

I thought it was going to be a normal Friday night hanging out with one of my friends, but this night turned out to be anything but normal. It all started out the same as one of our usual nights; we were just hanging out watching the basketball game and drinking a few beers and having some pizza. When the game ended around 11:30 Jason asked me if he could crash on the couch since he had had a few beers and he was kind of tired. I agreed even though I thought it was a little strange since he hadn't had that many beers, and he had never asked to stay overnight before. I went to my bedroom to get him some pillows and a blanket and said goodnight. I wanted to grab a shower before I went to bed like I usually do and while I was showering I couldn't stop thinking about him lying out there on my couch. I had thought about telling Jason that his longtime friend also had a feminine side Teresa who was attracted to him. I wondered what would happen if I shared my secret with him. The more I thought about him the more I found the hot soapy water of my shower sponge lowering down to my clitty until I became hard because I couldn't stop fantasizing about him. I forced myself to stop because this was surely a secret I could never share with him, because none of my friends knew about Teresa and I didn't think any of them would understand. I turned off the shower and slipped into my bathrobe and went out to the kitchen to get a glass of cold water, at least this was the excuse I made to walk past the living room and sneak a peek at Jason laying there on the couch. I tried not to be obvious and not stare just in case he noticed me walk out, but I couldn't help myself. He was lying on his back on the couch with no shirt on and the covers only pulled up to his waist. I was so turned on and I couldn't take my eyes off of him.

He was so hot just lying there I had get my glass of water and hurry back to the bedroom, because I knew if I didn't I was going to do something crazy like pull he blanket the rest of the way down and go down on him right then and there. I was so horny but I managed to get back to my bedroom and as I tried to get ready for bed I couldn't stop the fantasies running through my head. I decided I was going to do something bold, something daring, and give in to what I really wanted. Instead of telling him about Teresa, I was going to show him. This would be a night he would never forget and hopefully neither would I! I fumbled through my dresser drawer trying to decide just what I was going to wear, and I quickly pulled out my sexiest black lace bra and panties, and a pair of thigh highs with a garter belt and I slid into my long black silk robe and hurried to the bathroom.
I wasn't going to go crazy with the makeup, but I wanted to do just a touch and fix my hair so I would look sexy and hopefully turn him on. About 20 minutes later I was ready, and I looked really good and I slid into my 5" stiletto peep toe shoes and I was ready to give in to my fantasies and I was hoping Jason would be ready for Teresa. I went to head out of the bedroom and as I opened the door................I got scared! Damn it! I let fear take over, but I was still so horny thinking about him, but I couldn’t follow through with my plans. I carefully closed the door so I wouldn’t wake him and went to my nightstand by the bed and I pulled out a girl’s best friend! As I slowly started running my vibratory across the outside of my panties, the door opened a crack! Oh shit, I forgot to lock the door and I could see Jason peeking in but I acted like I didn't see him watching me and I kept on playing. He just kept watching me for about 10 minutes and I just laid there wondering if he liked what he was seeing or what was he thinking. It was driving me crazy wondering what was going to happen and just as I was about to say something, he pushed the door open all the way and I sprang up quickly and sat on the edge of the bed and tried to close my robe.

I was so scared and I started to cry because in that moment I was sure things weren't going to go the way I had thought they would. It was then that Jason said " Its ok, don't cry hun" as he sat down on the bed next to me. He wiped a tear that had just started rolling down my face and said “You look beautiful and don't be afraid, I've known for a long time”. He told me he had often wondered what would I think If he ever told me that he was attracted to me and when he house sat for me when I went on vacation he discovered Teresa's clothes he was curious about me and turned on even more. I guess I should have been mad that he looked through my panty drawer and whatever else he saw in my room, but in the moment I was totally fine with it. I was still scared when he leaned in to kiss me and I held back at first and tried to stop him. He looked at me and said “I know you want this to happen as much as I do" and I think that eased my mind and I gave in. It felt so good as he slid his warm tongue in my mouth and he started running his hand up my stockings and slowly undid my robe. His kept kissing me as he kept running his hands up and down my stockings and my clitty became instantly hard through my panties. When he got to the top of my thigh he felt it against his hand and he smiled and slid his hand down my panties. It was like heaven and he was so gentle as he touched me and continued kissing me. As he pulled that warm wonderful tongue out of mouth he looked at me and smiled and I said " I'm so glad I'm putting a smile on your face" and He said” lay down sweetheart and let me put a smile on yours" and he laid me down on the bed and slowly started kissing my clitty through my panties. His mouth was so warm, that I think I could have busted through my panties and he must have known I couldn't take it so he slowly slid my panties down. He started working his way up my leg kissing the inside of my thigh and put my hard clitty into his mouth. His mouth was so warm and wet as he took all of me in, and I didn't want him to stop and I begged him not to. He looked up at me and he said “if you liked that you’re going to love this" as he grabbed my legs and raised me up and put that long tongue to use in my tight ass. He was so amazing with his tongue that I could have just laid there for a week enjoying him and his magnificent tongue. I had never known anyone that could use their tongue in the ways Jason did to me............it was orgasmic! I could go on about his amazing tongue all day and you would never really comprehend just how amazing it truly was!

He pleasured my ass until I was close to cumming, but I wanted to wait and I definitely wanted to please him, so I pulled my legs down off his shoulders, sat up, grabbed his cock and started stroking it. I could tell he was a bit surprised when I took control and Jason looked at me and kind of laughed a bit and said “OH I like this aggressive side of you baby, so what’s next”, so I told him “It’s time to show you what I can do with my mouth” and I grabbed his shoulders, pinned him down to the bed and started kissing him again. I slowly worked my way down his hard body, kissing his chest and working my way down to his amazing abs, and his body smelled so good and he had me so horny that I wanted his cock in my mouth right then and there. As I kissed my way down his body, I kind of teased him a little bit and went right past his cock and started sucking and kissing his balls. In that moment I really wanted him to beg me to put it in my mouth, and I told him “Tell me how bad you want my mouth Jason”. He begged me and begged me for my mouth and after a few minutes I thought I had teased him enough so I took his hard cock in my mouth. I could taste the pre-cum on the head when I put it in my mouth, and that got me even more excited. His cock was so big at times it was choking me, but I kept going because I wanted it so badly. I worked every inch of his cock and every now and when I got him close to cumming I would stop and start running my tongue up and down the shaft. I wanted to take him to the edge and then bring him back, because I wanted him to save that load for later.

The last time I had him almost to the point of release, he stopped so he wouldn’t finish because he wasn’t ready and neither was I, so I reached in my night stand and handed him my bottle of liquid silk and I turned myself around on my side and continued to suck him, while he lubed my tight ass and begin fingering me. He slid his finger in slowly and asked me if I was Ok and when I told him it felt great he slid his second finger inside me and kept pushing in and out. I was ready, but a little scared since this was my first experience with a man, but I really wanted his cock inside me and I when he pulled his fingers out of me I climbed on top of him. I slid it in slowly and I do mean slowly since he was on the larger side. If I had to guess I’d say he was about 8”, but I wanted all of him inside me and I was going to take every bit of his cock. As I slid down on him, it felt so warm and amazing and I took it all, every bit of his 8” and as I started riding up and down on him I could hear him moaning and so was I. I started stroking my clitty while I was riding and he said “ Cum for me baby, Cum for me”, and It only took me a few minutes because his cock touched something inside me that made me cum almost instantly and I went all over his chest. He took his hand and cleaned of his chest and took as much as he could in his mouth and pulled me down and kissed me. It seemed a bit strange for him to do that, but I kind of liked it, the taste of my cum in his mouth. I pulled away and when I did he grabbed me but waist and pulled me down on the bed. I rolled over and pulled myself up as he got behind me, and he slid his cock inside me again. It felt like it went even further inside me and it felt so good I wanted him to cum inside me. He was going faster and faster and I had to put my face in the pillow and scream so I wouldn’t wake the neighbors. In this moment I really wanted to scream out loud, because it felt so good. I could feel his cock getting bigger and bigger inside of me and he pushed me forward really hard and in that motion I felt him cum deep inside me. When he made that push it must of hit that spot inside me again, because I came for the second time almost at the same time he did. I have to confess the second time was even better than the first, I’m guessing because we both went at the same time. I have never felt anything like that before in my life, it was the ultimate pleasure. When he pulled out of me he started tonguing me again and I could feel every drop of him running out of me into his warm mouth. This was so incredible words cannot truly describe how amazing this felt as well. After Jason finished working my ass for the second time, we were so exhausted we collapsed on the bed and I rested my head on his chest until we both fell asleep. I never knew how my first time was going to be, but it was an incredible experience, and I no longer have any fear. I hope I can have another night with Jason, but if not I will never forget this night or how good the first time felt.