Love The One You’re With

At one of my more embarrassing moments I found comfort in the person I was with.

Maybe it’s not difficult for others, but for me, being bisexual can really make your life complicated. If you’re dating a woman that doesn’t completely understand your sexuality and that no matter what she does, she cannot fulfill that desire for the opposite sex, life can become challenging.

When I was 18 I met a 42 year old man, Dave, that I lost my virginity to. Fell in love with. Nearly changed my entire persona for, and started living with him all in a matter of 2 or 3 months. Love makes you do things you never thought you could or would do.

As far back as age 13 I would dress up in my mother’s clothes. Something inside me just loves the way I feel when I am dressed as a woman. Now I have dressed as woman while being with a woman many times. In fact, my wife enjoys it from time to time. The cross dressing, at least for me, has no boundaries sexually. A lot of times I just wear women’s clothes while I’m lounging around the house.

With Dave, I had grown my hair long, waxed my entire body from the neck down, bought an entire wardrobe for in and out of the bedroom, and had an expensive makeup and perfume collection. With Dave, I was living as a woman and he always referred to me as his girlfriend. Now it may sound like I’m complaining but that’s not the case. It’s just simply put, I was wasn’t expecting it to go that far when we met.

Dave and I had now been together for almost 2 years. I was 20 and was now 44. He had a well paying career, I worked at the office with him and was paid a respectable salary, and honestly we had a pretty nice life together. We vacationed regularly. We had a nice circle of friends. Everyone at work knew our situation and respected us for the most part. And, we had a very great sex life that included other partners we’d bring in for threesomes or even more on occasion, and while Dave was completely gay, he understood that I was bisexual and that from time to time needed to that other side of my sexuality to come out.

Now, two years into our relationship, as I said I wasn’t expecting it to go this far and I started seeing that other side of my identity drifting further and further away and wasn’t happy about it. So, naturally there became some tension between Dave and I.

I had been strongly considering breaking up with Dave for a few months because of this. It wasn’t going to be a decision I made on a whim because we had spent 2 years together and really had some wonderful memories together.

One night I had decided I was going to go to a concert by myself. One of my favorite bands was in town and I wanted to see them. But, I decided to go dressed as a man. I went with two intentions. 1, see my favorite band and 2, try to remember what it was like to be in public as a male.

The night was going well, I am extremely introverted so I just kind of kept to myself in a corner of the club while the other bands I wasn’t really interested in played. While the band I was waiting to see was setting up, a girl approached me and she had the same shirt on as I did. It sparked a conversation between the two of us and sparks immediately started flying. I hadn’t spoken to a woman like this in over 2 years and was incredibly rusty and awkward. Fortunately for me she was equally awkward and uncomfortable.

I definitely do NOT have a type when it comes to lovers but if I did it’d be burly manly men with chest hair and big tittied goth girls. This girl was exactly that! She was a bigger girl, not huge but thick. She had long black hair, pale freckled skin, and a bunch of very cool tattoos. Oh, and very large tits!

We chatted for about 15 minutes while waiting for the band to play, then watched them together and went to a coffee shop afterwards to chat some more. I didn’t have a lot of experience or luck with women but I had never had this much success.

We continued our conversation as I walked her home and to my shock, she invited in! I to this day am still completely clueless when a woman is interested in me. It’s very easy to tell when a man is but for me, I am utterly stupid to a woman’s interest in me. Needless to say, I had no clue why she invited me inside her apartment.

Once inside she made us a couple drinks and within 20 minutes or so we were both a bit buzzed and our talking had transitioned to flirting.

I was relieved and indescribably excited when she made the first move and kissed me. It lead to a few more drinks and some intense making out and groping, although she had to literally pick up my hand and place it on her breasts to get me to grope her. At this point however, even I knew where we were headed and I was so unbelievably nervous. I had never actually had sex with a woman before!

We eventually made our way to her bedroom and began removing our clothes. Normally I am very self conscious about this part as I am an overweight guy but this particular I was very nervous. On top it being my first time with a woman, I was completely hairless. What was she going to think?!

Perhaps she, being a bit overweight herself, was self conscious as well and she turned off the lights leaving the door open for just a small amount of light in the room.

We now both were naked and very ready to go! I couldn’t believe how big her tits were and couldn’t stop playing with them. There was some very heavy petting! She stroked my cock as I fingered her for a few minutes. Her pussy was so fucking wet I couldn’t believe it! My curiosity grew. I had to taste it! I had never eaten a girl out before but I had seen it done a million times in porn so I just dove in!

She seemed to be liking it and my confidence began to swell. She draped her leg over my shoulder and arched her back. Her moaning became louder and louder. Her breathing intensified. Her hand held my head in place and she dug her nails into the back of my scalp. I couldn’t believe it, her pussy was getting wetter!

As she calmed down, she congratulated me on making her cum like that. I was so proud of myself. I was on cloud nine! I, for the first time in a long time, felt like a man! And then it all came crashing down.

I slowly climbed my way up her body kissing her belly and spending a moment or two with her fantastic tits. We kissed a few times. The tip of my cock eagerly bobbed and was tickled by her pubic hair and soaking wet slit. She lifted her legs and put them on my shoulders. I slid my cock inside her pussy with absolute ease. Instantly I felt like I was going to cum. I made my first thrust and I exploded inside her. I had never felt so good in my life to that point, but I knew I blew it, literally and figuratively. I was inside her for less than 10 seconds before I came.

“Are you fucking serious?!” She scolded me “…10 fucking seconds?! What the fuck?!”

“I’m so sorry! I don’t know what to say.” I pleaded

“Say goodbye.” She exclaimed as she rolled off the bed and threw my pile of clothes at me.

I said nothing as I dressed myself as quickly as I could and left. I had never been on such an emotional roller coaster. I was so high, feeling good about myself for the first time in a long time. Then it all crashed to the ground in an embarrassing wreck. I drove home sobbing, and feeling sorry for myself. I admit this was not the behavior of a man. It was by far my most feminine self coming out as I tried to drive home buzzed from the alcohol and countless tears in my eyes.

I was a frantic mess as I pulled into the driveway sometime around 2am. I sat in my car for almost a half hour trying to calm myself and stop crying. When I finally did collect myself, I got out of the car and walked in the house. Dave was fast asleep in our bed. I tip toed my way in our bedroom and grabbed some “feeling sorry for myself” clothes which included some soft white cotton panties, my most comfortable girly sweat pants, and an equally comfortable sweater.

I stood in the bathroom staring at myself for a solid two minutes splashing cold water on my face to try and hide the fact I was crying. I brushed my hair and put it back in a ponytail and at that moment I thought, maybe this is me. Maybe I’m just lying to myself about being bisexual. Maybe I’m just supposed to be this submissive cross dressing faggot. I never hated myself more than I did in that moment.

I decided not to wake Dave and just sleep in the couch instead. I put on a movie and started watching it. It was only a matter of minutes before I drifted asleep. I woke up a half hour later to Dave climbing over me. He nudged himself behind me in the limited space between me and the back of the couch.

He asked how my night went and I brushed it off and gave him as few details as I could. I had no interest in talking about it at all. Instead he just spooned me while we watched the rest of the movie.

As I laid there being spooned by this man that I admit, I was very much in love with, I began to feel a bit better. I tried to tell myself that it was just a bad night and there’d be good ones eventually and some more bad ones.

It wasn’t long before I could tell Dave was feeling frisky. While we spooned, he began running his hand up and down my leg. I admit I wasn’t feeling it at first but when he started kissing my neck, I felt his cock swelling against my ass. Given the night I had, I decided to play hard to get. That was a usual tactic I liked to play but was never good with it. Dave knew when I was doing it and knew exactly how to make me stop.

I pretended to ignore his erection poking my backside which we both knew I couldn’t. Dave had a fantastic 9” cock and when it was hard, it was very obvious especially spooning tightly on the couch. But, it was still fun to play the games. Plus, he kind of liked me playing hard to get. That’s why I did it.

When he had enough of my games, he slid his hand up my sweater and began playing with my nipple. At the same time he stopped kissing my neck and started sucking on my earlobe. Something about his mustache tickling my ear and his warm breath as he sucked my earlobe set me off. I was no longer in control of the situation.

I started to wiggle my ass a bit teasing his throbbing cock. Being overweight is always something that makes me feel bad about myself but I never felt that way with Dave. He loved me as much as I loved him and never made me feel self conscious about my weight. He loved my ass and I’m not gonna lie, I have an awesome booty.

Side note: Dave and I had a phase where we had a friend film us while we had sex and in some of the videos we made, my ass twerks as well as anyone’s.

But I digress…

Once he started with the nipples and the earlobe I was no longer in control of what we were going to do.

I reached back and grabbed a handful of his dick and began stroking and playing with it while he continued to grope my tits and nibble on my ear. Hearing him softly moan in my ear as I stroked his manhood was such a turn on.

“God I want you!” He whispered in my ear

I started to pull my pants and panties down but Dave’s eagerness took over and he wrestled them off my hips and pulled them to my ankles with his foot. Then he pulled his pants down and kicked them to the floor. We had kept lubricants in just about every room in the house as we enjoyed our spontaneous sex and didn’t like the idea of ruining a passionate moment by having to get up and grap some lube. He had the living room lube with him. This was all part of his plan.

In a matter of seconds I felt his hard cock pressed against my anus and still in the spooning position, he slid his cock inside me. He wrapped his one arm under my neck and his hand groped and played with my breast. His other hand placed firmly on my hip and ass cheek. His warm breath on my neck sent goosebumps through my body. His cock already buried as deep inside me as he could. We were as close as any two people could get.

Dave began to grind against me thrusting his powerful cock deep inside my ass. I was crying out in pleasure! I had never felt so close to him. After 5 minutes or so of spoon fucking Dave slid his cock out of me and told me to lay on my stomach. There’s no way I’m denying him if anything he wants.

He straddled me and without any hesitation shoved his massive cock deep inside me. Something about that position allowed him to go deeper than any other position. I loved it. I screamed into the couch cushion.

“Oh god yes, take me deep, baby! Give me all your manhood!” I screamed

My eyes rolled back in my head as he pounded my ass like the dominant male he was. All I could think about was how embarrassed I was an hour earlier when it was my turn to be a man and how impressive he was right now in this moment.

His cock slid in and out of my ass. I felt his balls slap me every time. I stuck my ass up so he could take me as deep as possible! Dave smacked my ass and grabbed onto each hip.he began pile driving his cock inside of me at an almost inhuman pace. Then he let out a primal scream and drove his manhood inside me one last time. I felt every pulse of his cock as it unleashed a hot batch of cum. I could feel the warm cum hitting the inside of my ass and filling me up. Dave yanked his cock from my pulsing asshole and squeezed out a few more drops of cum on my lower back. Then he slid is cock back inside my ass and began gently putting it in and pulling it out. He did this 5 or 6 times.
When he was finally done, he swiped up the few drops of cum on my back. I turned over and he put his fingers in my mouth. I loved the taste of his cum!

When we caught our breath, we got up and went to bed. We slept the way we always do, in that same spooning position. Dave fell asleep almost immediately. I laid awake for an hour or so thinking.

I knew I was bisexual. I loved being with that woman that night. But right now this was where I was needed and where I wanted to be. Dave and I loved each other. We had an incredible chemistry. We had no fear or shame of our lifestyle. Everything was good. Plus he could fuck all night and so could I… at least in the way him and I fucked.

Interesting twist to this story is that the big tittied goth chick I kind of had sex with.. turned out she felt bad how she treated me. Called the next day to apologize, and we talked for about an hour. Now it’s 20+ years later and we’re married. But.. that is an even longer story for another time….

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