Transsexual and Friend

It was an odd request, I'm sure but one I had been thinking about for a while. "Go on...", said Jessie, sitting across from me at a table at our "mutually convenient" coffee shop in the city. "Well, I'd would like a certain massage experience, I'm a bit nervous to go myself and I'd like you to hold my hand" (so to speak).

Given what I was now broaching and due to the fact I was now talking in hushed tones, I thought I'd better come right out with what I wanted from her. "I would like to get a massage from a transsexual and I was wondering if you would be there to help calm my nerves".

Jessie and I had previously worked together at a property company for about a year. She had left the job about 18 months ago and we had caught up (over coffee) only once before since she left.

I further explained that I couldn't ask another guy or anyone in the office and I certainly didn't want to ask my wife. She hadn't got up and left, so I took that as a good sign. "It would be during lunch time, it's just down the street and you'd be doing me a big favour". I added, without thinking, "I'd be wearing underwear". This was a bit of a half-truth. I may start wearing underwear, but I would be expecting them to come off reasonably quickly.

Jessie had just turned 40. She was an Asian lady (Chinese) but had grown up in Australia so her English was perfect. She was very attractive and bubbly. She also had very large breasts. I'm not so much into breasts but I used to see her in the office wearing these suits that were always very tight in the chest region. I personally thought that if she had the choice she wouldn't have such a large chest (she likes to run, for example) but you get what you get. "Ok", was her reply.

I had in fact previously been with a transsexual (by the name of Sugar) who was a very attractive Thai lady. In fact I had been with her probably about five times - always just for a massage. On my last visit I had asked her if it would be ok if I brought someone along next time to watch. Without waiting for her to ask, I offered her an extra $100 for the half hour if she was happy with that arrangement. She was and accepted. I told her further I was going to pretend this was my first time with her, so we would have to remove some of the familiarity out of our relationship and go back to the time when we first met. She understood.

The date was set for Thursday next week at 1:00pm. I had the booking with Sugar and arranged to meet Jessie outside her office.

The day took ages to arrive but it was finally here. I sent a text to Sugar at about 12:00pm to remind her of the booking. I didn't hear back from her until 12:30pm (that was a long 30 mins) but she confirmed and explained that she had just woken up. I headed down to pick up Jessie with plenty of time. I let her know I was at the bottom of her building and she sent a reply text saying she was on her way. When she arrived I gave her a quick hug. Not something that we normally did but it seemed appropriate in the circumstances. "You still OK with this?", I asked. I knew that if she had reservations I would probably have heard from her during the week. Still, it was reassuring when she said, "Yep, let's go".

We arrived at Sugar's building close to 1:00pm. In accordance with her usual procedure, she asked me to text her 5 minutes before arriving which I did. I then texted her to say we had arrived. She came back to say she needed a few minutes. That was a bit worrisome. It was OK for me to wait but I didn't want to hold up Jessie, particularly on her lunch break, particularly when there was nothing in it for her.

Within a minute or so we were directed to press "15" on the keypad and then the bell symbol. Sugar buzzed us in and we went up to level 4. We arrived pretty quicky and the door was ajar awaiting our arrival. I slowly went in with Jessie trailing. Sugar was wearing a big towel (just having had a shower herself) and welcomed us. I made quick introductions and then asked if I could have a shower myself. Sugar furnished me with a large white towel (which I swapped over for the agreed $200). I left Jessie on a chair in the dining room (it was an open plan apartment) and went off to the shower.

I quickly got undressed and turned on the water, not wanting Jessie and Sugar to make anymore small talk than they had too. Although I was already pretty clean after having had a workout then shower mid-morning, I wanted to make sure I was fully clean. Washing myself I was already starting to get a little hard, which wasn't necessarily a bad thing.

Normally I would walk from the shower to the bedroom naked as it would be just Sugar and me. This time around and, as "promised" I put on some reasonably tight, black underwear. I went with the underwear I usually wear for running which keeps things in place without moving around. Leaving the bathroom I could see Sugar lying on the bed, still in her towel and Jessie on the dining room chair that had been brought in for her. Both were on their phones.

They looked up when I entered the room and duly put down their phones. I paused for a moment to let her (and myself) take it all in. I had been working out virtually every day for the last 10 months or so and I must admit I was probably in the best condition of my life.

Sugar motioned me to come to the bed. I laid down on my back with my head on the pillow and my legs pointing to Jessie who was seated at the end of the bed. Sugar then took off her towel and propped herself next to me. She had long limbs, a smooth tanned body and nice big breasts. She faced away from Jessie so her genitals were not yet visible to her. If she didn't know any better, Jessie would have assumed that she was a woman.

Without pause Sugar slowly started to massage my thighs and legs. I instinctively reached out and ran a hand up her back. I was perhaps a bit more familiar with her than I should have been in meeting her "for the first time". Before long Sugar started touching my crotch area and ran her hands over my underwear. My bulge was starting to become apparent.

Perhaps quicker than I expected, Sugar took off my underpants. I didn't resist and my penis flopped out to the side. I couldn't see Jessie at this point as Sugar's body was in my eyesight. Although quite a bit nervous, I managed to get quite erect quite quickly. I imagined Jessie's gaze was fixated on my dick getting bigger and harder.

Sugar then put a leg across me and mounted my body backwards (that is, facing Jessie with her bottom facing me). This was the first time Jessie would have seen Sugar's penis and confirmed her "transsexuality". Sugar bobbed down as she inched her bottom up toward my face and I got my first sight of Jessie looking at us as she leaned forward in her chair slightly.

Sugar had now brought her crotch right up to my face and was solely focused on working over my cock which was now rock hard. She moved it around and was playing up to the audience of one.

I reached up and stroked Sugar's bottom and slowing slid my hand down to her scrotum. She had the biggest balls I had ever seen - much bigger than mine (although I didn't have a big range of comparatives). This carried on for a few minutes. I couldn't quite reach her penis at this stage but I knew we would have time to get to it. Sugar backed herself right into my face and so it was easy for me to nuzzle at her balls and then open my mouth and start to lick them gently. I knew from previous visits that she liked this.

Eventually Sugar went on her knees to the right side of me and exposed her cock right near my face. Now Jessie had a view of both our dicks. This was my opportunity to reach out and touch Sugar's penis. It was still soft and only a few inches long. I looked at it as I fondled it, feeling its softness and it slowly starting to get hard.

I alternated between her cock and her balls while she continued stroking my cock. Once she was semi hard, I opened my mouth and took her inside me. She still had her foreskin and as I sucked, I used my hand to pull on the skin, exposing the softness of the head of her cock to my mouth and tongue. Sugar was starting to become hard. On her website she notes that her cock is seven inches long. I had known for a while that this was an overstatement as I was around seven inches myself. Sugar would only be about five inches fully erect.

I was struggling to cum so I grabbed a hold of my cock from Sugar and started stroking myself. Given I couldn't both touch her cock and jerk myself at the same time, I asked Sugar to move across to the other side of me. She did so and I carried on, this time now holding her balls while I sucked on her. Goodness knows what thoughts were going through Jessie's head at this stage.

Sugar now focused on fondling my balls. Sensing I was struggling (I had struggled the last couple of times), Sugar motioned to Jessie to come over. This wasn't something I had discussed with Sugar beforehand. I didn't have a problem with it, I'd love it in fact - I just didn't want to betray Jessie by going beyond what we agreed (well, beyond after already having taken off my underwear).

Jessie look flushed and giggled a bit as she shook her head. However she soon got out of the chair and knelt down beside the bed to get a better look. I took my mouth off Sugar's dick, looked across and locked eyes with Jessie. This was actually quite hot. I'm sure if I had asked Jessie to simply watch me masturbate I would have had no chance. Yet, here we were with me not only masturbating but also sucking on a gorgeous transsexual's cock.

About a minute or two later Jessie reached out to my balls. Sugar took her hand away and Jessie started some light touching and tickling. While she was doing much lighter touches than Sugar, suddenly it was the most sensual thing on the planet. I sensed and orgasm and held by dick up slightly as my cum shot out of it and onto my chest and stomach. I couldn't believe all of what had happened. Jessie retreated her hand, probably with much the same feelings.

Sugar reached behind her for some tissues and dabbed them on me. It was a quick clean up as Jessie moved back to her chair at the foot of the bed. Sugar offered me a shower again, which I went and took. It was again a reasonably quick one and I was dressed in double time.

I thanked Sugar and gave her a hug. She was all smiles to me and she escorted us to the door. Quickly checking there was no one in the hallway she let us out and we made our way back to the lift.

I walked Jessie back to her office building - which for some reason felt like a much longer walk than when I walked her an hour earlier. All I could do was to thank her for coming along and telling her it was an amazing experience I couldn't have done without her. "I'm glad you enjoyed yourself", she smiled. We arranged to catch up the following week for coffee, which I'm sure would include a bit of a recap and debrief.

* * *

As we left each other I said to her I was thinking about writing a story about today's events and publishing it on Literotica. Jessie said, "Yes, but remember the last story you wrote where you got a lot of negative comments and in fact had to delete your story?". I said yes, I remember. And in this story most people would have expected me to have written that you ripped off your clothes and we all had a three-some with plenty of fucking and double-teaming. But, "What is better - a completely made up story with a bit of spice or a bit more subdued story that was based on actual events and provides real memories for the future?". "Clearly the real life story", Jessie said. "Well I hope the readers of Literotica agree and keep their comments nice", I submitted.

So I hope everyone enjoyed the story, based on real life events - everything except that last piece of dialogue of course (!)