This is the story of the first time my first boyfriend and I fucked. Before I get started I should give you some background information about myself. I had always considered myself straight and had been happily married for fifteen years before my wife and I drifted apart and divorced. While we were married I had wondered what wearing some of her heels would be like. Unfortunately my feet were too big and I couldn't wear them properly. I would also occasionally try on her sexy underwear and parade around the house when she wasn't home.

After our divorce I found myself thinking more and more about wearing heels and lingerie until I finally broke down and bought a pair of black four inch pumps and some sexy underwear. I couldn't get over how sexy everything looked and felt. I found myself wearing them more often and buying more and more lingerie. Soon I started wondering what it would be like to be with a man. I posted a couple ads and had a couple of meetings dressed as a woman, one was great, two were good, and 1 was okay... This is the story of my first encounter with the guy who would become my first boyfriend.

I was excited as I arrived at the motel and checked in. I had been texting Mike for a couple of weeks, and there was something about him I found very sexy. He was twenty-four, six foot tall, chubby, with a five inch cut cock. I was excited he was sizteen years younger than me and could get it up multiple times. My other partners were around my age and were one and done.

Once I arrived in the room I unpacked my stuff and jumped in the shower to clean up inside and out. Once out of the shower I got dressed. I put on a pair of black cage style underwear and a pair of white thigh high stockings, covering everything with a black pencil skirt. I then put on my sexiest pink laced bra and cream colored blouse. I wore a pair of black four inch platform heels. I then applied my makeup, long fingernails, and put on my red shoulder length wig. Then I settled in and waited for his text that he was in the parking lot.

After what seemed like hours he texted me he was in the parking lot. I opened the door and noticed him standing outside his car. I did my best to walk in a seductive manner towards him. As I got closer I noticed he had gorgeous blue eyes and I imagined myself looking into them as I sucked his cock. Once close enough I leaned in to kiss him. He responded eagerly and next thing I knew our tongues were in each others mouths. 

He had me worked up and wanting to touch his cock. I fumbled with his zipper and was able to touch his hard cock for the first time. I was surprised how hard and thick he was. I loved the feeling of it in my hand and couldn't wait to put it in my mouth. I broke off the kiss and led him by his cock up the stairs and into the room.

As soon as the door closed behind us I was down on my knees and sucking his cock. After about a minute he pulled me up and kissed me. His hands were all over my body and Mike was paying special attention to my breasts, ass, and crotch. Mike unbuttoned my blouse and began to play with my nipples under my bra. I had let him know how much having my nipples played turned me on. After a few minutes of Mike pinching my nipples I couldn't take it any longer and broke our embrace.

I stepped back unzipped my skirt and let it fall to the floor leaving me in a bra, panties, thigh highs , and four inch heels. He let out an audible gasp and I dropped to my knees with the goal of draining his balls.

As I pulled his pants down I could see precum on the tip of his cock. I flicked my tongue across the tip and was rewarded with a taste I knew I would grow to love. I couldn't take it any longer and began to suck his dick for all it was worth. Mike began to slowly thrust his hips and fuck my mouth causing me to suck harder and stare into those eyes.

After a few minutes of this he grabbed my head and let his load go in my mouth. I did all I could to swallow his sweet load but some of it dripped down my chin and onto my chest. I kept his cock in my mouth as it spurted out its last few drops and then slowly cleaned it up until he went soft. He pulled me onto my feet telling me how awesome that was as he gave my a kiss and pinched my nipples. I told him we had only just begun and to get comfortable while I cleaned up.

Still feeling horny I went into the bathroom to clean up. During our conversations I had told him I had a few different outfits depending on how I was feeling. I had met him in my conservative, business type outfit. He had been hoping for the slutty do anything outfit. He had me so turned on I opted for the slutty outfit. I put on my red corset with matching fishnet stockings (which I bought just because he likes fishnet stockings), red crotchless underwear, red six inch fuck me stilettos, bright red lipstick, and my nipple clamps. I looked in the mirror and satisfied with how I looked entered the bedroom again.

Mike saw me and let out an audible "Wow!"

I responded by telling him I was all his and he could use me however he wanted. He looked like a kid in a candy store and motioned me over to the bed next to him. As I got closer to the bed he reached out and grabbed my cock and started to suck on it. At that point I knew he was as horny as I was because he had told me there was no way he would suck another cock and here was mine in his mouth. As he continued to suck on me I leaned over to suck on him some more.

This time I was not in a hurry and just admired him for a bit. He was smaller than me but much thicker. I slowly started to lick his cock and just enjoy how it tasted. . I would lick his shaft and head and then slowly slide it into mouth until my nose was in his pubic hair. I would linger like this and then stick out my tongue and lick his balls. I would the release his cock from my mouth and suck his balls.

The whole time he was playing with my cock and I kept telling him how good it felt. He then stood up and pulled me so me head was hanging off the edge of the bed. Mike then proceeded to slap his dick on my face and then put it in my mouth. This went on for a few minutes until he started to really fuck my face, He then moved up and made me lick his ass. As I rimmed him he started pulling on my nipple clamps. The harder he pulled the further my tongue went into his ass.

He then started playing with my cock and finger my ass.

After a couple minutes of pure heaven I told him I needed his dick inside me. Mike changed positions and began to face fuck me again. It was not how I wanted him in me but I wasn't complaining. His thrusts became harder and next thing I know he is cumming on my face. I did my best to catch some of it but I was a mess. He then pulled me to my feet and gave me a very passionate kiss and told me to clean my face. I told him to lay down and I would be right back.

When I returned I went down and immediately cleaned his cock with my tongue. I was really horny at this point and wanted him to fuck me. After a few minutes of cleaning his cock and getting no reaction I figured he was done. He pulled me up next to him and gave me a passionate kiss that I hungrily returned. We made out for a few minutes with him gently tugging on my nipple clamps and slowly stroking my cock. I worked my hand down to his cock again and started to play with it.

After about ten minutes of this we stopped kissing and playing with each other we just lay there next to each other making small talk. I told him what an incredible fuck he was and that I wanted to meet him again. The only difference was next time I wanted that cock in my ass. He returned the compliments and said he was going to fuck me today once he rested. We continued to talk and idly caress each other.

Next thing I know Mike is concentrating on my nipple clamps. His gentle tugs and pinches are starting to get me worked up. Mike then surprises me by gently biting and sucking on my nipples. This is more than I can take and I make it my goal to get him hard again.I start by gently tugging on his cock.

Mike pushes my hands away and tells me it's his turn. He then returns to biting and sucking on my nipples. The harder he bites the more excited I get. He then adds to my pleasure by playing with my cock, balls, and ass. Mike kisses his way down my stomach until he gets to my cock. He looks up at me with those gorgeous blue eyes and devours my cock. As Mike is doing this I'm moaning his name and telling how amazing he his. As he inhales my dick he slides his fingers in and out of me. He continues this for a few minutes and I can feel his cock start to get hard on my leg. As I feel it growing his mouth on my cock and fingers in my ass become more intense. I'm losing my mind and tell him I need his cock in my ass.

Mike flips me onto my hands and knees and moves in front of me. I put his hardening cock in my mouth and suck him until he becomes rock hard for the third time. I remind him to put a condom on and Mike reluctantly puts one on and moves behind me.

Mike slowly rubs he head of his cock up and down my ass. I relax and slowly push back into him. He continues to tease me before I feel him slowly push into my ass. I let out a gasp as his cock head squeezes into me. He slowly pushes into me until I feel his balls on my ass. He is not long but his girth feels good. He stops and bends over to kiss my ear and gently pull on my nipple clamps as I tell him how good his cock feels.He slowly pulls out and slides back in. Each time he does I let out a low moan.

He continues the slow in and out motion as I beg him to speed up. He slowly starts to speed up and I'm moaning louder. He grabs my stilettos and picks them up forcing my head onto the bed. As he thrusts in his cock hits my prostate driving me crazy. After a few thrusts like this he pulls out.

He has me so turned on I'm begging for him to fuck me faster and harder. He lays down and tells me to ride him for a bit. I lean over give him a big kiss and climb on his cock. I slide easily onto him and I enjoy the sensations until I feel my ass on his balls. I lean over and give him a passionate kiss that he hungrily returns.

I break our kiss and lean back with my hands on his ankles. He thrusts into me and grabs my cock at the same time. I encourage him and we fuck like this for a few minutes. Wanting a different feeling I rotate on his cock and ride him reverse cowgirl for a few more minutes.

Mike then reaches around and slowly strokes my cock. Feeling his cock buried in my ass and hand slowly stroking me has me ready to cum. Not wanting to cum yet I move so I'm laying on the bed. Mike moves to the end of the bed and pulls me toward him. He pulls my legs onto his shoulder and easily slides into me. Mike just stays there letting me enjoy the feeling of his cock in my ass. He grabs my cock and starts jerking it.

Mike can tell I'm close to cumming and he starts to fuck me hard and fast. I'm moaning and telling him how much I love his thick cock. Hearing this his thrusts increase and I can tell he is close to cumming as well. I move my ass to meet his thrusts and we are both groaning in pleasure. He moans he is cumming and I feel him release his seed inside me. At almost the same time my cock starts to twitch and I shoot my load all over myself.

Mikes thrusting stops and we both lay there basking in the afterglow. He slowly scoops my cum off my chest and offers his fingers to me. I happily accept and greedily lick my cum off his fingers. We lay there kissing with his spent cock still inside me. Not wanting this feeling to end, I wrap my legs around him and pull him into me. after a few minutes he goes limp and pops out. I reluctantly released my grip and Mike backs away and removes the condom.

I grab his wrist and tell him I want to taste his cum one more time. He immediately understands what I want and pours the contents of the condom into my waiting mouth. Enjoying the taste and wanting more I put his limp dick in my mouth to get it clean.

 I looked at the clock and realized we had been fucking for almost an hour and a half and thought to myself that was the best ninety minutes I had spent in a long time. I told Mike he was a great fuck and I wanted him and his cock again soon. He replied in kind and we made plans to meet again.

Mike and I would meet again and we would eventually become boyfriend/girlfriend and have many more adventures.

*****

Thanks for reading. It's my first story, let me know what you think. If you like it I can write about more of our adventures.