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Gay for a day

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Gay for a day!

The perfect set of circumstances aligned and I fulfilled a long time fantasy.

I had little bi/gay experience in my past- mostly on the oral side of bi play from a male friend of my parents when I was younger. Certainly enjoyed the oral play, but was never asked to reciprocate- thus the idea of such never dawned on me at the time. Many years later, many married years at that- I never had the opportunity to explore any of my bi side feelings and interest.

Like many- I enjoy a wonderful marriage, but also like many- it is often about balance. Our friendship, parenting and other facets of our relationship are perfect, but our sexual interest and/or appetite are very different. I keep my sexual appetite satisfied via a very active fantasy and masturbation life- one she knows about and supports.

I have often thought about what it would be like to perform oral sex on another man- but also have never experienced any actual attraction to men.

A few weeks ago, a petite person approached me online and began to chat with me about my interests as well as theirs. Shortly after the fun exchange began- details began to flow. As it turns out, Bob was now going by Bobbie. Bobbie was in the process of getting a sex change, the remaining item being- a cock. Shortly after I would find out, and eventually see via pictures- Bobbie was all woman albeit the one added/missing item. This turned me on to no end- fed my overall attraction to women, but potentially provided the opportunity to explore some bi/gay experiences that Bobbies cock would still provide.

Making this match even more inviting- Bobbie (like me) has a small cock. As a newbie with oral sex, this was less intimating- and as an anal virgin- equally appealing.

Skipping several other exchanges- eventual phone calls- we set up a time to meet when I would be on a rare business trip where I would be traveling solo. I made up my mind- this would be perhaps my only opportunity to explore this fantasy- so I committed to myself to be fully "gay for a day". Short of pain and obvious safety items- I was open to anything. Bobbie and I discussed this as well.

The day of our meet finally arrived. I had never groomed, washed and re-washed so much in my entire life (later to find Bobbie experience the same). I checked in first and registered for my convention and quickly returned to my room- waiting for Bobbie was like waiting for Santa when I was younger!

Bobbie arrived at my door, and was I pleasantly surprised! Outwardly she was 100% woman- and beautiful and sexy at that. While I had dreamed about taking a guy's cock into my mouth over the years, the idea of kissing another man has always grossed me out. As such, imagine my surprise when I grabbed the back of Bobbies head and pulled her to me and began to French kiss her with every emotion I had to deliver. She was soft, tender and sensitive- a pleasant surprise. We continued to kiss and grind on one another before eventually moving our hands into more sexual parts of our bodies. This was a mix of the virginal feelings when first moving through the bases with a girl in high school with a mix of romance and positive sexual tension.

Slowly we each began to remove one clothing item after another. After what seemed like an eternity- we were both now standing in front of one another in just our underwear- each sporting a raging hard-on.

Bobbie and I had discussed earlier the need for us to delay my climax, as unfortunately like many, I realized ahead of time my inhabitations would be reduced dramatically after.

Bobbie removed my underwear and immediately took my cock into her mouth. Bobbie devoured my cock in such a way that I have never experienced. This (sucking my cock) is obviously something she enjoyed greatly. This brought even greater enjoyment to me as my wife does not enjoy providing oral sex, so it's hard to be but so excited when you know she's not enjoying the experience as well. Once I got to the point I knew I could not take it much longer, Bobbie rolled me over and jumped into my ass. She spread my cheeks and began teasing my inner ass - blowing on my hole, licking me with tender flickers only to eventually and fully take my asshole into her mouth, and fuck me with her tongue.

After a positive eternity, Bobbie introduced lube to my ass and began to finger my ass, starting with one finger, after another. We had discussed this prior- so I knew what followed would be her mounting me and taking my anal virginity. As if on cue, I heard a condom being opened and seconds later, the pressure of her cock replaced her fingers in my ass.

I had played with toys in the past- and knew I was tight- so her small cock was perfect. Felt much better than any toy I have ever tried previously as well. Tender fucking was followed by fast and furious sessions (liked the tender more). I could tell Bobbie was close and within a matter of seconds, she pulled out, pull off the condom and placed her cock in my mouth just in time to blow her first stream of cum into my waiting mouth. This was of course another first for me- and one I will remember forever. My only regret was (due to my inexperience) I swallowed so quickly not knowing how much to expect. Once I realized Bobbie was finished- I didn't have any more remaining to savor in my mouth.

We took a short breath, but quickly started on the reversal of roles. Once Bobbie softened from cumming in my mouth, I moved to her balls and quickly to her shaven ass.

A few side notes- Bobbie was completely hairless short of the hair on her head and the "landing strip" just above Bobbies cock. As such, a shaven ass is a major obsession of mine. My wife only occasionally lets me rim her. What she doesn't seem to realize- from when I first began having oral sex with woman, my standard approach is from top down- as such, when eating pussy, my nose is always in their ass! As a result (obviously cleanliness aside) the smell of bathed ass actually ignites my sexual juices.

Back to Bobbie's ass- Bobbie helped spread the cheeks making the hole and surrounding hot spot even more accessible. The more I licked and sucked, the more Bobbie moaned. This inspired me more and I simply dug deeper. Before long I swear I must have had half of my ridged tongue deep within Bobbie's ass. Eventually my aching stiff cock drove me to the point of realizing I must stop devouring Bobbie's luscious ass, and prepare to lose my giving side of anal virginity. I began to lube Bobbie's ass although it seemed fully ready already. Slipped on a condom and prepared to insert my cock in the first ass of my life. I pushed slowly and was surprised at the resistance given how loose Bobbie's ass appeared. Bobbie encouraged me to keep pushing slowly so I complied. Once I pushed just a little more, I quickly slipped in the rest of the way- fully to the point my balls were fully pressed against Bobbies firm, but still soft ass cheeks. Given the go, I proceeded to slowly fuck my lover for the day. The tightness of Bobbie's ass took my back to my teens when I first fucked a pussy. The emotions coursed throughout my body, enjoying every stroke both inward and out. I too realized I had returned to the point of cumming soon- before I could state such, Bobbie sensed the stiffened cock as well. Just like I had experience, I pulled out and removed the condom only to look up and see Bobbies waiting and wanting warm mouth. I few powerful sucked from Bobbies mouth with a few aggressive strokes from my hand and I began to release what I am sure is the strongest ejaculation of almost 40 years.

Just as planned, after some small talk Bobbie dressed and left, I expect never to be seen again. Likely never to be experience on my end again with anyone- but the memory can never be taken away.

I returned the following evening to my fantastic wife. I also returned to my physically heterosexual life- but I will always remember my "gay for a day" experience.

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