What a bitch. We’d lived together for almost two years. As long I as had good money coming in, she was happy to give me all the suck and fuck I wanted. But not two weeks after I’d gotten laid off, she dumped me. Not even in person at that, I got back from the employment office to find my place cleaned out, and a “Dear Jay” note from her.

Which was appropriate I guess, as my name is Jay. Hi there, didn’t mean to sound so bitter, but I suppose you need to know the frame of mind I was in. I guess if I sounded bitter it’s because I was. I had actually thought to marry the bitch. It was quite a blow to find out I was nothing more than a sugar daddy for her.

Unencumbered by ties, or furniture (she’d taken most of it) I prowled the net until I found a new job, in a new town. Hell, not just a new town, a new country! I moved from the sunny south (Atlanta) to Toronto. I told everyone I was going to turn over a “new leaf” in the land of the Maple Leaf.

I found a tiny but affordable apartment in the downtown area, near where I worked. I had been there about three months before the loneliness really started to set in. By that point the rush of a new job had calmed down, and I found my evenings free.

Stressed out, I finally decided a massage was in order. But from where? I checked through the paper, looked at several ads, and found one for in home massages. Perfect, I thought, I won’t even have to go out. I placed the call, and set the time for Saturday afternoon.

I’d had massages before, but it always ran the gambit so I wasn’t sure what to expect. Deciding to play it safe I wore my bathrobe and underwear while I waited for Dale to arrive. Dale was the name of the person who I’d ordered the massage from.

Right on time the door bell rang. I opened the door to discover Dale was a real looker. She was probably five foot eight, with a pretty face and long blonde hair. Her thin frame made her huge breasts look even bigger, had to be a D cup under that tiny black dress. The skirt stopped just below her crotch to show off her long legs.

She came in, and I offered her a beverage. Dale was cheerful and friendly, so I suggested we talk for a bit first. I guess the loneliness was apparent as she agreed. We talked for almost an hour, me giving my sob story and her telling how she was working her way through school. Comfortable, I finally suggested we get started with the massage. Dale got a funny look on her face, and got serious.

“Look Jay. You seem like a real nice guy, so there’s something you really ought to know.”

I shrugged my shoulders. “Sure, go ahead.”

“Well, it’s like ... you see, most of my customers already know and I just ... well I mean it’s not a big deal it’s just that some guys expect certain things and before we start I guess you ... well I just...”

“Look, it’s cool. Just spit it out. I’m easy.”

“Well OK, now don’t freak or anything it’s that ... well... “ Dale took a deep breath. “I’m a transsexual.”

“Pardon?”

“I ... uh ... well most of me is a girl but I got guy parts down ... there.”

Of course I knew what a transsexual person was, but it still caught me by surprise. “Oh. OK.” I paused for a moment to reflect, but she went on.

“If you want me to leave just say so, it’s just that some guys well they get to expecting things and others just want a massage and don’t care and well you seem like such a nice guy and all I just wanted to make sure and be upfront and all.”

Frankly her (clearly Dale preferred the female pronouns, so I’ll respect her and use them as well) revelation didn’t bother me too much. In my early teens I’d had a few male playmates, and we’d played around with each other including sucking each other off. I was in college in the very early 80’s and it was rather in vogue then to be bi, and a few times I’d had some fun with guy friends including my roommate. Of course that was twenty plus years ago, and since then I’d been a devoted pussy chaser.

“Look, it’s cool.” I said as assureingly as possible. “I don’t have a problem with it. I called for a massage, and that’s what I’d like.”

Dale let out a deep breath, in relief. “Great.” she said, a big smile coming to her face. “What say we get started?”

We adjourned to the bedroom where she covered the bed in a blanket from her bag. She noticed me standing in my underwear and said “You might want to remove your briefs as well. I use a lot of oils, and wouldn’t want to mess them up. If you want we can cover you up with a smaller towel.”

I thought about it, but have never been that hung up on nudity, besides which I figured it was nothing Dale hadn’t seen before. I dropped my drawers and stretched out on the bed face down. I felt her small hands begin to work the oils into my skin. Soon she was rubbing all over, and I was lost in pleasure.

During the massage we talked about past relationships. It got pretty graphic as I described some of the things my ex-girlfriend and I used to do. I told Dale how she was a real cum slut, loved for me to spunk all over her face and tits. Also how we loved oral and anal sex.

One example I told was how my ex used to fuck me with a double headed dildo, one end in her twat the other in my backside. Then we’d swap and I’d ram my cock up her sweet ass while reaching around and pumping the dildo (still in her) with the other.

“So how about since you moved up here?” Dale asked.

“Nothing.” I replied, a hint of disgust in my voice.

“Nothing? Nothing at all?”

“Well, just me jacking off. Been so busy I haven’t had time to meet anyone.”

“Must be awfully frustrating.” she said. I agreed and told her so.

Dale continued the massage in silence for several minutes. Finally she said “Look, I don’t usually mention this on a first time massage and all, but um ... well for a few extra dollars I can make sure you are ... well TOTALLY relaxed.”

Intrigued, and more than a little horny, I asked “Let’s be candid. You’re offering to get me off. Just how would you do it?”

“A variety of ways. Some of my customers request a hand job. Others enjoy a titty fuck. For a select few, I will perform oral sex for them.”

“And will you be naked for this as well?”

“If you want. Some of my customers want me to leave on my panties, others like to see it all.”

It was a no brainer decision. Really, my dick made the decision for me, no brains were used at all. “OK. I want the full thing. And if I’m paying that much, you’d better be nekkid.”

Dale stood up beside the bed. I rolled onto my side to enjoy the show. She peeled the black dress up and over her head tossing it to the floor. Her black panties were French cut, riding high on the thigh. She grabbed the waist band and asked “Are you sure you want it all the way?”

I nodded. “Let’s see it all.” She dropped them to the floor, kicking them off. I got to see her dick for the first time. It wasn’t huge, but not tiny either, probably about five inches. Her crotch was totally shaved, completely hairless. “Well?” Dale asked nervously.

“Nice. I like it.” I rolled onto my back. “You go ahead, I’m putty in your hands.” Dale smiled and slid back onto the bed. She really applied the oil now, getting a lot of it onto both our bodies. Wordlessly she rubbed me all over, teasing my stiffening cock.

She then began stroking it, bringing it to full erection. I groaned in delight. “Jay.” Dale said quietly. “Would you prefer a blow job, or a titty fuck.”

“Gosh, I dunno. What YOU prefer to do?”

She seemed taken back that someone might actually care what she wanted. She thought for moment then said “Me? I want to feel your stiff cock in my mouth. I want to feel it slip past my lips and hit the back of my throat. I want to run my tongue over the tip, I want to taste your hot spunk as it floods my mouth.”

Damn, that was all I needed to hear. “You got it.” I replied. “Go for it.” I gasped as Dale leaned in, taking my manhood into her hungry mouth. I spent several minutes of glorious bliss, as she sucked and licked my cock. I fought back the urge to cum several times, although I don’t know how.

The way Dale was positioned on the bed, her head was pointed down, and legs near the head of the bed. That left “her” cock near my head. I reached over and tentatively touched it.