Jess and I had been dating for almost a year. Everything in our relationship was great and her ability to charm just about every person she met, made me the envy of my group of friends. I knew I had a few very jealous male comrades and quite frankly, it made me feel great. And they really only knew the tiniest bit about her.

Our sex life was as fun and adventurous as always and Susan joined us regularly for threesomes. She had undergone quite the transformation and was a much more self-assured lover now. I was pretty sure that most of her focus was on Jess rather than me but I was not complaining. I found her gangly, pseudo-supermodel physique a huge turn-on and enjoyed both our physical and intellectual interactions.

Plus, there was something incredibly erotic and entertaining watching her and Jess go at each other. There were times when I’d just sit in a chair with a glass of wine and watch the two of them play.

While I was very protective of Jess and our relationship, I never saw Susan as a threat and there were times when I secretly had entertained thoughts of us in some sort of threesome relationship but was not sure how something like that would even work. As usual, I found myself getting ahead of myself and consequently filed that idea away for the time being, not wanting to disturb anything about our relationship in its present state.  The old saying of “Don’t fix it if it ain’t broken” was very applicable here. I was not about to mess with what was a very nice situation.

Considering our somewhat libertine ways, the conversation about an open relationship came up at one point. I was relieved to hear that Jess was just about as uncomfortable with that concept as I was. We did agree that we would allow ourselves to play with others, as long as we did it together. That seemed appropriate considering that in some way that was how our relationship was founded in the first place.

One Sunday morning, while lounging around, talk turned to how we first met at Terry’s party and how we ended up as participants in that crazy sex game he had arranged.

At one point she brought up the incident when Terry sucked my cock and commented on how I did not seem that freaked out about it at the time.

She asked if I had ever played with other guys and though I gave her a very diluted version of my experiences with guys, I did admit that I had always had a curiosity for cocks. She really perked up and kept drilling me about it. Even though we were completely open with one another, this line of questioning made me somewhat uncomfortable and I found myself trying very hard not to reveal things that I thought she might not want to hear as opposed to being completely open.

I was overthinking again.

Inevitably she finally asked if I’d ever consider having another guy join us.

Deep down inside I just did not want to to imagine another guy sticking his cock inside her while I watched but I knew that admitting that to her straight out would be the height of hypocrisy, considering that I was perfectly content sticking my dick into Susan when we played with her.

Maybe Jess was just more open-minded than I was. 

I also told her that whereas I did have a thing for a nice cock, I really was not attracted to men. It was the truth. Playing with a buddy was one thing, but it was more about addressing basic horniness and a sense of exploring the forbidden and unknown.

I had never had the same reaction to a hot-looking guy walking past me on the street as I did when a cute girl passed by. The dynamic between a couple of buddies was fascinating to me but there was never any real physical attraction.

It was becoming obvious that Jess had already decided that a second cock was going to be part of our play at some point and in typical fashion she had already come up with a solution. She caught me a bit off guard when she suggested that we find a transsexual to play with us.

I had always had a fascination with she-males as they addressed both of the things I liked, the outward appearance of a girl but with a male attachment.

Playing with one had been a recurring fantasy of mine and now my girlfriend not only permitted but also encouraged the idea.

I tried not to look too pleased when I told Jess that I would go along with her plan.

Naturally, the first question that came to my mind was whether she already had someone in mind. That’s usually how it went, with her being several steps ahead of me. When I asked her, she said that she did not and that we would have to start from a blank slate.

Even in a town like San Francisco, finding a she-male suitable to our specific situation was not going to be easy but I also knew that Jess would find a way to see this through in some way. Time for me to hang on for the ride.

There was a great nightclub and bar that I used to frequent when I was single, a cool underground space that featured music, food and a very diverse, hip and fun crowd. I was always amazed at how many shemales, transvestites and cross-dressers frequented the place. I told Jess about it and suggested that we might try to go there to find someone to play with.

We decided to go that very Sunday evening. Saturday nights were mayhem with three deep at the bar at all times but while Sundays still drew a good crowd, the scene was much more relaxed.

As we walked down the long stairway to get to the lower level, Jess was already reprimanding me for having never taken her there. She instantly loved the place.

I made some stammering excuses that did not sit well. The reason that I had not taken her there was because, in some sense, I had always considered it as my place, where I used to hang out in my single days. Somehow I wanted to preserve that memory strictly for myself.

The fact that I had gotten a little more than close with a couple of the female bartenders who still worked there, also acted as a bit of a deterrent.

There were several groups of she-males there that evening but they seemed fairly cliquey and hung out amongst themselves. Unfortunately, most of them were dressed and made up in an over-the-top style that bordered on comical in some instances. The heavily made-up bombshell look.

Jess and I agreed that that was really not our thing at all.

There was one particularly stunning, very tall goth girl that immediately caught my attention. Between her high-heeled boots and tall spiked hair, she stood as tall as me at over six foot four.

I had always been attracted to that style and fashion sense and dressed in a very subtle goth style myself, a sort of elegant dark look which Jess actually appreciated but when she saw me make fairly significant eye contact with the girl, she stopped me in my tracks and told me that that was a bit much for her.

I kept the fact that I was quite disappointed in myself.

There really were no other prospects that evening. But there was no great urgency, so we decided to just keep looking. Something would come our way.

The club did offer the best prospects so we focused our energy there. It had also become one of Jess’s favorites and ended up going regularly. A couple of uncomfortable hurdles involving my past single days had to be crossed but I was also happy to be hanging out there again.

A few weeks later we were having cocktails at the bar when we noticed three girls sitting also sitting at the bar, a few stools away from us.

They looked fairly plain. Two of them seemed to be a couple and they definitely had a lesbian air about them, leaning toward the more butch side.

The third girl was kind of pretty in a way that was hard to pin down. She was wearing a simple, knee-length, sixties-style sundress and some suede Chelsea boots. Her shoulder-length hair was parted on the side and looked to have been dyed a dark blueish tint but it was hard to tell for sure in the dimly lit club. She was wearing generally very subtle make-up except for some very dark eyeliner that made her large, pretty pale blue eyes really stand out. It made her look exotic and kind of dorky and quirky all at the same time.

I found her quite cute and pretty.

At some point, her two friends departed. Jess gave me a kick and nudged me.

The girl took out a notebook and started to write and draw in it while continuing to sip her cocktail. When she finished it, Jess jumped into action and quickly ordered another one and a couple more for us.

She looked surprised when the bartender suddenly placed the drink in front of her and she made an inquisitive motion. The bartender pointed at Jess, who gave her a little wave.

She looked confused and asked why we had bought her a drink. Jess said that we were just getting ours refilled and we might as well get her one too since she was by herself.  She smiled and thanked us and continued to draw in her book.

I knew it was just a matter of time before Jess would escalate matters to the next level. The girl seemed shy and absorbed in her drawing but when Jess asked her to join us, she slid over to sit next to us.

When it turned out that both of the cocktails she and I were having had the same, fairly exotic French liqueur in them, Jess took that as the perfect catalyst to start the conversation. We introduced ourselves and found out that her name was Alexis.

I figured that Jess had some idea about our new acquaintance but I was still trying to ascertain her true gender by gathering any clues I could.

Her voice was soft but a bit raspy. She had very smooth-looking hands with long slender fingers and short nails that were painted blue. Her boots looked large but not completely out of proportion to her frame. The slinky dress she was wearing revealed small, perky-looking breasts but that was not conclusive proof of anything either.

At this point, she was still an enigma to me, though I was leaning towards thinking that she was just a typical, alternative-leaning city girl.

Jess went to work with her prodigious social skills and charm and was soon extracting all sorts of information.

She was an art student, originally from the East Coast, lived in the city and was single. 

The conversation took off and we talked about art, music and life in the city in general. There were a lot of overlaps with things we liked and were interested in.

It was getting late and things in the club were winding down. Alexis was getting ready to leave and thanked us for the drink. Before final goodbyes could be made, Jess asked Alexis if she would like to join us for brunch this coming Sunday.

From the look on her face, Alexis was as blindsided by the invitation as I was. We never really had brunch. I’d usually grab a coffee and pastry and Jess would wolf down a bowl of cereal in the morning, so inviting a stranger to brunch struck me as weird.

I could see her struggling with the decision and was honestly quite surprised when she accepted. Jess smiled and gave her a big hug. I finished my drink while they exchanged numbers. Chalk one up for Jess.

On our walk back to her place she made her case as to why she thought that Alexis was a shemale. I was not convinced yet but if Jess was going to do her thing in her usual fashion, it might not be a lot later than Sunday before I had some definitive proof in front of me.

Sunday morning came and we met Alexis at a small cafe. She was waiting outside when we arrived, wearing a similar outfit to the one she had the other night.

She was also wearing a small leather choker around her neck giving her otherwise cute girl look a bit of a sexy edge. Even in broad daylight, I could not detect anything that would have given me a clue. She just looked like a pretty girl to me.

The sunlight did reveal that her hair had a definite blueish color to it. It did not look gaudy but did impart a bit of exoticness to her look.

We settled in at a table. The girls ordered Mimosas while I opted for straight sparkling wine. The conversation pretty much took up where it had left off the other night.

Alexis told us that she had just recently moved to the West Coast from Rhode Island. She intimated that situations at home sought her looking for a drastic change of scenery and even though she was still just settling in, she felt very much at home here.

Jess offered to show her around town and they were already making shopping plans. It was quickly becoming obvious that the two of them were hitting it off quite nicely. I found Alexis quite charming and figured that even if nothing else happened, we had at least made a cool new friend.

As brunch came to an end, Jess asked Alexis if she had any plans for the day. 

When she said that she did not, Jess immediately asked if she wanted to come over and hang out with us.  We’d tear apart the Sunday newspaper, drink some wine, and listen to some music.

I was pleasantly surprised when Alexis immediately accepted the invitation.

We got back to the apartment and settled in. It was a warm day and I opened a bunch of windows to allow a bit of a breeze, put on some music and got a bottle of wine and glasses while the girls were getting comfortable on the couch.

The afternoon was getting warmer and warmer and Jess decided to get more comfortable by changing into some shorts and a tank top. She had also taken off her underwear by the looks of it.

She asked Alexis if she wanted to get more comfortable too and offered her some shorts and a top.

Again, Alexis immediately agreed. I guessed that she intended to stay for a while.

Nobody offered me to get comfortable. Must be a girl thing. No guy would ever offer another guy a change of clothes to get comfortable when he came over to visit.

Alexis came out of the bedroom in similar attire to Jess’, shorts and a small black tank top. I was still trying to get my piece of evidence but it looked like she had kept her panties on under the shorts, preventing any indication of what she might be hiding. The short-cropped top she was now wearing did reveal that she had a belly button piercing.

She had very pale, almost white skin and had painted her finger and toenails to match the blue tint of her hair. It made for an almost alien look. She was about five foot ten with a solid build.

I did notice that her hips were fairly narrow and her shoulders a bit broad with some muscle definitions in her arms, but again, nothing out of the ordinary. Her long legs would look good on a guy or a girl. So I was still perplexed.

The two of them were quite chummy on the couch, going through the paper, and chatting. I made sure everyone’s glasses remained filled and entertained myself by watching them. Two, well maybe two girls being very girly.

It was a perfectly pleasant, lazy Sunday afternoon.

At one point Alexis started to stretch out her back a bit and explained that her new job, working in the shipping department of a local clothing designer, was getting to her physically. There was a lot of awkward lifting involved and it was starting to take a toll on her back.

Jess immediately jumped up, got behind the couch and started to massage Alexis’ shoulders. She let herself relax, closed her eyes and gave into Jess’ touch.

When Jess’ hands started to explore more of her body and the touch became more and more sensual, I knew where this was heading. Alexis looked like she was really enjoying the attention and was moaning lightly. Jess’ hands moved to her chest and as she leaned forward to reach them from behind, Alexis’ head was cradled by Jess' breasts. Both looked to be enjoying themselves.

I was starting to get hard, watching all the sensual activity right in front of me. 

And I was not the only one.

A small bulge started to appear in Alexis’ shorts. Jess was right all along.

My mind was racing now, wondering how this was going to play out. This was completely new territory for me and I found myself getting nervous. Was Alexis into guys? Girls? Both? How would I fit into this?

She certainly seemed to be enjoying the attention from Jess who had now moved around to her front and was massaging her legs. As she moved up her thighs, Alexis suddenly clenched her legs shut and looked really embarrassed.

Jess gave her a tiny kiss, then gently spread her legs apart and softly traced Alexis' growing erection with her finger. This seemed to relax her again and Jess cuddled up next to her before proceeding to caress every inch of her body.

I was about to burst out of my pants watching the two of them but stayed in my chair. It seemed more prudent to let things develop a bit more before I would decide if or how to join them.

They had a certain dynamic going that I really did not feel part of yet.

I went to the kitchen to open another bottle of wine and realized that it was our last one. Since it looked like our guest would be staying for a while, I decided to go to the local wine shop and replenish our supply.

I told them but got no response. They were so engrossed and focused on one another that they seemed oblivious to anything around them.

I just left on my errand.

I sure got an interesting surprise when I got back. The two of them were naked and making out.

Jess always did work fast when she wanted something.

She was gently stroking Alexis’ fully erect cock while they were kissing. It was not extraordinarily long or thick but nicely shaped with a slight upward curve. Alexis had her hand buried between Jess’ legs.

I sat back down in the chair and watched, trying to get a look at our new friend.

There was not a single hair on her body. The smooth, almost white porcelain-like skin and the blue hair and nails were even more striking, now that she was completely naked.

Well, not completely naked. She was still wearing the leather choker. That look is a huge turn-on for me to this day.

She looked truly androgynous with her somewhat boyish body but otherwise quite feminine features, including small pointy breasts that looked to be the result of some sort of hormone therapy.

I was enthralled.

The girls seemed to be completely oblivious to me being there but that was ok. I was enjoying the show and still had not come up with a course of action. I figured Jess would give me a signal or something when they were ready but a this point it just seemed all about the two of them.

The heavy make-out session had now progressed to them intertwined in a sixty-nine position with Jess on top. Alexis was feverishly liking and kissing Jess’ pussy while Jess was busy swallowing Alexis’ cock.

I was now stroking my own through my pants.

Suddenly, Jess looked over at me and gave me a look that I only knew too well. It was the “come fuck me” look.

I quickly stripped off my clothes and went over to the couch. I knelt behind Jess, my cock just inches above Alexis’ mouth. She pulled away from Jess’ pussy and to my complete surprise, grabbed my cock and slipped it into her mouth, giving me several strong sucks before guiding my cock into Jess’ pussy.

A great barometer of how turned on she was, was always how wet she’d be. This time it was like dipping my cock into a swimming pool.

Alexis had contorted herself into a position which allowed her to tease Jess’ clit with the very tip of her tongue. I was beneficiary of that too as she’d also lick my cock and balls as I was sliding in and out of Jess.

We kept fucking like that for a while and even though there was little friction due to Jess’ incredibly wet pussy, I was soon starting to feel that familiar feeling come on.

I thought I could hold on for a while until I felt one of Alexis’ fingers playing with my anus. She was playfully rubbing and poking until that finally put me over the top and I exploded into Jess’ pussy. After a couple of strokes, Alexis pulled out my cock and wrapped her lips around my shaft as I continued to cum.

She still had cum dribbling out of the corner of her mouth when she sat up on the couch. Jess quickly moved in and cleaned Alexis’ face up with her tongue.

We composed ourselves enough to all sit up on the couch and have some more wine.

No one really said much and while there was a bit of an awkward silence, there was no weird, uncomfortable feeling.

Eventually, the two of them were sprawled out on the couch together and I went to sit on the floor in front of them.

We had barely resumed a conversation when Jess announced that she had a fantasy. She wanted to watch me suck Alexis’ cock.

Alexis did not seem flustered one bit by this and actually had a bit of a wry smile on her face.

I, of course, went through my standard procedure in my head, weighing out all the consequences and possibilities that might result. What I did know for sure was that I’d have Alexis’ cock in my mouth sooner than later.

We sat there in silence until Alexis took the initiative. She stretched out her left leg and placed her foot squarely on my chest.

I had not paid much attention before but when I looked down and realized that she had really pretty feet. Though I had always appreciated pretty feet on a girl, I never was really obsessed with that like some guys were but now I found myself suddenly really attracted to this “girl’s” feet. They looked incredibly soft and smooth with long straight toes, immaculate toenails and great-looking slender ankles.

She started to playfully tease my chest and nipples with her toes, moving from my bellybutton to my neck. My cock started to twitch and swell immediately. Alexis noticed and moved her other foot to my lap, gently teasing my cock with her long toes.

It felt amazing.

Jess seemed quite fascinated by all of this and watched us intently. I closed my eyes and let my body relax as Alexis kept up her foot to play with me. I suddenly felt her toes on my face, first caressing my cheek and then on my mouth. They wiggled them to pry my lips apart. It felt really strange but I suddenly felt compelled to open my mouth and wrap my lips around a couple of her toes.

Other than some playful little fun with Jess’ feet, I had never experienced anything like this. It had always seemed just a little weird. But now I found myself licking and sucking what were technically a boy’s toes and feet and finding it one of the more erotic things I had experienced.

I looked up to see that Jess and Alexis were embraced in a passionate kiss again.

I took that as a sign of approval and continued, licking the soles of her feet and sucking her toes. Alexis seemed to be loving the attention to her feet, squirming and contorting her body.

Jess was watching intently. I was glad that she had really cute feet too because I could tell by the way she was reacting to all of this, it would be incorporated into our regular play sooner than later.

At one point I ended up with both of Alexis’ big toes in my mouth at the same time. This seemed to send her into an elevated state of pleasure.

I saw that her cock was dripping pre-cum like crazy, so I decided that it was time to address Jess’ wish and give Alexis’ cock the same attention I gave her feet.

I slowly worked my way to her ankles and then up her calves, licking and kissing all the way. When I moved past her knees and up her inner thighs, her breathing got noticeably heavier. She draped her legs over my shoulders, spreading them wide, giving me unobstructed access to her cock, balls and anus.

I  gave her ass and scrotum a little lick on my way to teasing her head with the tip of my tongue. Her body shuddered and tensed up a bit as I licked up the droplets of precum.

Jess had cuddled up to her on the couch to give herself a nice vantage point to watch the upcoming action.

I gently wrapped my lips around the head and slowly let the length of her cock slide into my mouth. It was rock hard and throbbing but the skin was silky and smooth. The slight upward curve worked as an advantage as it naturally seemed to contour to my mouth and throat, allowing me to swallow her all the way to the base.

I had sucked a couple of buddies cocks but this felt very different. It was the same organ but had a much more feminine feel to it, making me take a more sensual approach, kissing, licking and sucking very gently. Feeling her body respond, I thought I was on the right track.

I had watched Jess sucking her earlier and I knew her approach all too well. Aggressive but with finesse at the same time. Mine was very different

It was certainly not like any kind of competition but I was hoping that my gentle technique had the optimum effect on our new friend.

I was ecstatic that it all felt so natural. I had dreamt and fantasized about a scenario like this but now, with it really happening, it felt almost surreal.

My brain worked overtime trying to process the fact that I was sucking a she-male's cock while my girlfriend watched.

After what seemed like a very long time, I could sense a change in Alexis' reactions. They were becoming increasingly more intense and I could feel her muscles tightening up. I know I was getting her close and started to suck a bit harder and more deliberately.

Her buttcheeks suddenly clenched and I felt a gush of warm, salty liquid in my mouth. When Alexis slowly pulled her cock out, Jess immediately jumped down from the couch and buried her tongue in my mouth.

I had not swallowed Alexis’ cum and Jess was now swirling it around my mouth. Some of it dribbled out and ended up coating our lips and chins.

If the bemused look on Alexis’ face was any indication, we must have been quite the sight. Jess quickly went over and planted a deep kiss on Alexis.

Now all three of us sported a similar look. After a bit of cleanup in the bathroom, we returned to the couch and put our clothes back on.

Alexis stayed for a while but declined Jess’ offer to spend the night with us. She did accept the invitation to another brunch date for the next Sunday.

Jess and I were already seated at the table when Alexis arrived, wearing what looked to be her standard attire. A simple, casual dress and to my delight, another leather choker.

But instead of the usual boots, she was wearing a brand new pair of spaghetti-strap sandals.

.