To me, getting ready throughout the day to have sex is so exciting. The anticipation and not being able to focus on nothing but pleasing a man all day is so unbelievably hot to me. I am a passable Crossdresser that has had my share of hot sexual encounters but it never gets old pleasing men. I ran an add online several months back and I began chatting with a handsome tall guy. We talked about all kinds of things in life and of course sex. We planed on meeting up several times but things always came up to derail our plans, that’s life. One of the biggest issues was that he is married. Yep married! See, I have never had anything to do with married men, I always felt it was so wrong so I would shy away from it. Something came over me though, a certain feeling that aroused me to the point I can’t control, I always believed it feels so good to be so bad.
Aaron is his name, contacted me after a few weeks of not speaking and just said, wife is out of town via text. The biggest smile came over my face. It was a Friday during the day and I’m still at work. I ask him if tomorrow would work and he replied “yes but let’s please do this”. I promised him I’d come through this time as my weekend was absolutely freed up. We chit chatted about what was gonna happen all evening Friday.
Fast forward to Saturday morning. First thing I did was take a hot shower and shave my entire body smooth(not a big deal cause I stay smooth). I then proceeded to get a pedicure and had my toenails and nails painted white. Time was really flying so I had to get home and get prepared which takes me forever ugh! I began my makeup and I went with my fav, Smokey eyes. Applied my makeup to perfection and added some light pink lip stick. I selected to wear a tight pair of jeans with white tennis shoes. White lingerie top that was just above my pierced belly button. It fits beautifully on my nipples and I put on an over jacket that just covers my shoulders and arms. Looking in the mirror I was so horny for this married man I couldn’t stand it. Feeling a little guilt because I knew it was wrong but it felt so right deep inside me.
I then added my blonde wig and brushed it to my liking. I looked absolutely passable and delicious! I grabbed my small bag I keep my necessities and lingerie in and headed out the door. Aaron lives about 30 minutes from me so I turned on some RB music for the mood. I had to stop to get gas and decided to walk inside to get some gum. All eyes were on me, I honestly didn’t know if they knew I was a crossdresser or not but I didn’t care, I was sexy, horny and on my way to get fucked. I arrived at his house which was super cute and nice. I pulled into his driveway and noticed a Range Rover, rich bastard I thought haha! Get out and the biggest guilt shot over me but gosh it felt so so good! I couldn’t what to taste this man!
I knocked on the door and the hottest man I’ve ever seen opened the door smiling, he said “ Jessica you are here” I said in the flesh haha dork! He lead me inside his beautiful home and poured me a glass of wine, I didn’t bother to tell him I hate wine, I just sipped it with him as we began small talk. Aaron told me he’s always had a fantasy to be with a girl like me, said he’s had opportunities but always chickened out. This was during the winter so he had a small fire lit in his beautiful romantic living room. He politely showed me around his 9 bedroom 4 bathroom house while we continued to sip on nasty wine. I was more interested in looking at his fit body and nice sized arms. He had spiked hair with a tight black long sleeve shirt that fit nicely on his arms and fit body and jeans. He looked so yummy and delicious I wanted him in my mouth.
We finally returned to the living room and he turned some soft music on, fuck music to be exact, he encouraged me to make myself comfortable so I sat down on this comfortable huge couch. I took my over jacket off and he hung it up for me like a true gentleman. We made small talk as he sat close beside me. He smelt so wonderful as he slightly kissed my cheek and neck. I let out a small moan as it felt so damn good. He slightly kissed my lips as I told him I need to use the restroom to freshen up. He showed me the way as I carried my small bag with me. I entered the restroom and slowly removed my clothes and put on an awesome lingerie set that included pink thigh highs and a black garter. Placed a blk choker around my neck and pinned my hair back. Belly button and nipples pierced and put a silver chain around my waste and inspected myself in the mirror that I’m sure his wife uses often. I thought to myself, sorry maam he’s all mine tonight. I’m tan all over so I said fuck a shirt I’m ready.
I walked out of the restroom and he was sitting on the coach with anticipation as I walked slowly toward him. The fire glistering off my body was so fuckn hot! He stood up and we immediately locked lips. He caressed my horny body as our tongues were in each others mouths. I was so erect and hung I just moaned at his touch. He told me” you don’t know how long I’ve wanted to get you right where I have you”, I immediately dropped to my knees and slowly undid his belt and unzipped his pants as his big beautiful cock sprang out pointing right at my face. I began to rub his shaved balls while admiring his big dick. It was probably 7 inches shaved with a mushroom head. I noticed precum at the start which is so sexy to me. I began to lick his cock up and down kissing the head and sucking his balls. He was so big and smelt so wonderful I knew he was all mine. I began to slowly suck his cock taking him all the way in my mouth. He moved the hair out of my face and told me to look up at him. On my knees sucking his dick I was looking straight up at him like I was told. He was moaning and moving his mouth to the rhythm. I tasted his precum and it was salty while i continued to suck his dick with my sloppy saliva. He said “OMG baby I’ve never had my dick sucked like this”, I’ve actually heard that before haha.
After several minutes of pleasing this married man orally, he had me stand up. He at once picked me up as I wrapped my long stocking tanned legs around him. I thought, fuck me he’s strong and man handling me! He began sucking my pierced nipples and I wanted to just eat him up. He slowly laid me down on his couch and removed his shirt, now I could see his entire rock hard body and omg! Aaron spread my legs slowly apart with his hands on my little feet and began tongue fucking my ass and licking it, it felt so good damn I was squirming and moaning. This went on forever it seemed as I thought I was gonna cum from it but I didn’t. Aaron asked me if I liked it as I replied “I love it baby I love every bit of it”. He then straddled my face and once again his big cock was down my throat. I began sucking that dick as he face fucked me. I was wanting to taste him cum but definitely wasn’t ready for this to end. He pulled his cock from my mouth and he stood up pulling me to the edge of the couch. Still on my back legs opened wide he guided his swollen hard dick against my butt hole. I could feel that slippery head sliding against my asshole waiting to enter.
After teasing my ass for several minutes he slowly inserted that 7 inch shaft inside me! I almost lost my breathe with excitement as it slowly massaged my prostate with each thrust. I knew I was an absolute homo as this hit man began fucking my brains out. I couldn’t help but think, how did this used to be a ladies man now become a hot little sissy in lingerie getting dicked down by a man in his living room! It was so hot who cares, I couldn’t do anything but moan and move my hips while I looked down and observed his big dick penetrating me as he picked up the pace. Fucking me over and over I fell into ecstasy as I placed my arms above my head gripping a pillow. I kept feeling myself about to cum but it would stop just to start again. This guy was absolutely taking any little bit of manhood I had left in me! Dick stabbing my asshole, sweating and moans echoing throughout the room I began to get light headed, I thought holy fuck am I about to cum from anal?! I’ve never ever done this. No guy has ever made me cum from anal, I felt it getting more intense as the guilt, shame and the pure excitement of this overfilled my body, I began to cum hands free, my body began to shake and shiver, I was moaning blacking out and cumming! Omfg I was cumming so hard I couldn’t believe it! I knew it was like a drug and that I was done! No more pussy ever for me!
He slowed his pace and continued to slowly penetrate my horny sissy ass until he was about to explode, I quickly sat up still tingling from what just happened. He emptied his entire balls into my opened mouth, I swallowed all that I could but lots ran out of my mouth soaking my little pierced tits. I just fell onto the floor as I was breathing hard, covered in cum and sweat. My asshole was still buzzing and dick still hard. The absolute best fuck ever! He has one lucky fuckn wife!
