First Time Bi

I had been bi-curious for many years. As a young man in the military, I got a blowjob in the Philippines by what I thought was a girl. After she sucked me to completion, I noticed an extra bulge in her skirt as she turned to walk away. I was a bit taken aback by that, while at the same time intrigued. I was 19 years old and a walking hard on for anything in a skirt, but I was really into girls.

I spent most of my life cross dressing, sneaking into my mom's room to try on her lingerie. I liked the way it felt and it made me hard as a rock. As I got older, I started collecting my own clothes. Bras, panties and pantyhose were plentiful and easy to purchase just about anywhere. I dressed in private, enjoying myself dressed up, looking in the mirror and exploring my body.

I got married and had children, enjoying the sex life of an early married couple. But as time goes on, it gets kind of stale and I am more sexually adventurous than my wife. I took opportunities when possible to dress up and have some fun. It was during this time that I got very bi-curious, remembering the time in the Philippines.

I started chatting with other bi and gay men, trading stories and sex chats. That progressed into photo trading and a lot of masturbation. Video chat introduced me to a whole new world of stimulation. I could masturbate with another guy, dress up and role play, etc. Many different scenarios played out and it was all incredible and stimulating. Most of it I had not done, but was developing a great desire to experiment and try.

I started using a dildo, having only used a finger in the past. It took some time to get myself stretched out enough to really enjoy it, but I wanted to feel what it would feel like to have a cock in my ass. My first one had a slight bend at the end that brushed against my prostate as it went in and out. I used the straight end at first. One night I decided to flip it around and insert the bent end in. It hot my prostate with every thrust, causing a huge amount of pre-cum to drip out of my cock. As I increased the tempo, I could feel myself tingling and ready to cum. I was on my back with my legs slightly up and the first few shots of cum hit me in the face. It was my first experience feeling that, and while shocked at first, it was erotic as hell! The orgasm went on for longer than normal and was more intense than I had ever experienced.

I had been chatting with Frank for a few months, sending him photos of me in my various sexy outfits. He would send back photos of his hard cock. It was turning me on to know that he was getting a hard on from my photos. He told me many times that he wanted to fuck me.

I was traveling on business and was going to be in his town. He said he wanted to hook up while I was in town. I was intrigued and nervous at the same time. I knew from his photos that he had a cock that was just about the right size for my first time. The thought was exciting, but I was very nervous as it had been many years since I had been with a guy. I didn't know if I would still like it, or if he would suddenly not be attracted. I decided to agree to it. He wanted me to dress up for him and he would come to my hotel room.

We agreed to meet at 6 PM at my hotel. I texted him my hotel and the room number once I arrived. I had plenty of time so I showered, shaved and tried on various outfits, checking the look in the mirror. I picked a black bra and panties with stockings. I didn't want to be fumbling with panty hose and I wanted to be able to keep the stockings on while we played. I grabbed a short black skirt and a silky print top. My hair was long at the time, so I styled it in more feminine way and applied some makeup. I rarely use makeup so it took a while to look reasonable. With the lights dim, it should be okay.

He texted me that he was on his way as I was finishing my makeup. He was about 20 minutes away and now with nothing to do but wait, my mind raced and my nerves were going crazy. I was excited and nervous at the same time. I paced the floor, getting the feel of walking in my girl clothes to be more feminine and to burn off some of the nervous energy. I dimmed the lights and got ready for his arrival.

There was a knock on the door and my heart skipped a beat. I stood up and straightened my skirt, looked through the peephole to make sure it was him, alone and opened the door with me behind it. He walked in and looked me up and down as the door closed. He grabbed me around the waist and said "God, you're gorgeous." Then he pulled me into him and put his lips to mine. I had never kissed a man before, so I was taken aback, but I liked it. His hands reached back and cupped my ass as he pinned me against the wall. Our tongues explored each other mouths as my hand went down to his cock, which was already rock hard. I could feel it through his shorts, throbbing and hard. He let out a groan as my hand reach into his shorts and took his cock gently in my grasp.

He hiked up my skirt and pulled my panties down as I was pulling his shorts down. He then push into me, still pinned to the wall, our cocks grinding together. His hand moved all along my body as I kissed his neck an shoulders, unbuttoning his shirt and sliding it off. My tongue slid along his neck, down to his chest where i nibbled on a nipple while my hands worked his cock and balls. I was so turned on! I got down on my knees and kissed and licked around his balls before gliding my tongue slowly along his shaft to the tip. I licked along the head of his cock before taking it into my mouth. He moaned loudly as I glided his cock into my throat, savoring it. He took my head and started fucking my throat as my hand reached up to caress his balls as he fucked my face. I opened my eyes to look at him while I sucked his cock. He was enjoying it.

Suddenly, his hands were on my face and puling me upward. He kissed me deeply and passionately as he led me to the bed. He took off my skirt and blouse as he kissed me before shoving me down on the bed and getting on top of me. His cock was grinding against mine as we kissed, tongues darting in and out of each others mouth. I rolled him over and went down on his cock again, sucking away as my head bobbed up and down. He was moaning with passion as my tongue and mouth remembered what felt good done to me and the results were clearly working. I could feel his cock and balls tighten and he grunted "I'm going to cum!" As the last word came out, he started spurting a big load into my mouth. It was a lot of cum and it was more than I could take at one time. I gagged slightly because there was more in there then my mouth could hold. Some of it slipped through my lips as I tried to swallow it all down.

As the last of the spasms ebbed, I licked up the cum that escaped and licked him clean. He forcefully shoved me down on the bed and took my cock in his mouth. He sucked me for a while as I stroked his cock back to fully erect. As I moved to 69 with him, he stopped me and said he wanted me to cum. I took his cock in my hand again and said "You will make me cum when you put this in me. Fuck me, Frank!" He didn't need any more prompting than that.

I was on my back. He reached to the nightstand to grab the lube. He put some on my ass, then ran a finger in me while he put lube on his cock. His finger found the spot and pre-cum was flowing out of my cock head. I was very close to summing before he pulled his finger out of my ass, then raised my legs up and guided his head toward my virgin hole. It hurt a little at first as I was a little tense, but he slowly eased all the way in. He leaned forward to kiss me passionately as he started slowly moving in and out of me. I had my share of dildos in my ass over the years but this felt incredible! We kissed as he fucked me and I was getting very close to summing before he took his cock out and rolled me over. I got up on all fours and he slid into me from behind. It was bliss! He put his hands on my hips and started fucking me hard, with long strokes. I could feel his balls hitting against mine with every stroke. I reached back to fondle his balls while he fucked me deep.

His hand came around my waist and took hold my cock, stroking it to the rhythm of his fucking. I could feel his balls tighten up as mine were. I started cumming hard. The muscle spasms working my sphincter muscles put him over the edge as he exploded into my ass as I was coming. He kept stroking through the end of the orgasm, resting himself on my back as our breathing slowed. He pulled out of me and collapsed on the bed with a sigh.

I got up to clean up a bit in the bathroom. When I came out of the bathroom, he was dressed again and ready to leave. We kissed passionately for a few minutes before he said he had to go.

I told him I was in town all week if he wanted to get together again before I went home. Now that I has experienced sex with a man again after all these years, I wanted more. We ended up getting together a couple of nights later and one more time before I left. Frank took me from bi-curious to bisexual, and it was awesome.