The Pool Boy's Message

The week dragged and only made lighter when we met for our swimming workouts. Given these were public, our displays of affection with strictly curtailed. However, we did perform oral on each other.

When Saturday finally arrived, I received a text from James telling me to let myself in when I arrived. His parents were financial comfortable with a large house on a leafy street in an affluent suburb.

I parked around the corner so as not to arouse suspicion and discretely entered the house. I called out to James who said he'd be down in a minute or two and to help myself to a drink.

Grabbing a beer, I sat in the lounge room and rubbed my crotch in anticipation. I had not long to wait. When James entered the room, my jaw dropped to the floor and my cock nearly exploded.

In front of me was a young woman of incredible beauty and dressed in a maid-like outfit. The face was made up with extended eyelashes and eyeliner. The lips were heavily rouged, the cheeks flushed. There was jewelry dangling from both ears and the blonde hair parted into twin pigtails. The chest had a lacey bra (stuffed with socks), the crotch with crotchless panties with a recognizable bulge poking against them. The legs were covered in sheer black stockings and the feet daintily clad in red high heels.

"Hi, I'm Jane."

A hand was extended to me to kiss.

"Nice to meet you, young lady!" I croaked and stood up.

'Jane' did a twirl for me and asked me if I liked her transformation. I answered in the affirmative. He had done an incredible and convincing job, alright. The face alone would fool even the most astute observer.

"Wow, look at you!" I marveled while feeling up his feminized body.

James bent over the couch while I squeezed his buttocks and slapped one cheek hard. He let out a squeal of satisfaction. Running a finger between the crack, I felt the butt plug in place and my hard cock twitched.

"How long have you been 'Jane'?"

"Today is her first proper outing," James replied, enjoying being felt up by his older lover.

"This is your mother's?"

"Yep," He giggled seductively, "Is that wrong?"

"Not from where I'm standing."

I grabbed a ponytail and pulled James to me and kissed him passionately. When we disengaged, he laughed as his lipstick was smeared over my face.

"When did this all start?" I asked, rubbing his rock hard and leaking penis.

"A couple of months ago," James replied, rubbing his hand across my clothed chest affectionately, "I tried on some panties and almost came."

James went onto say that his mother has a significant toy and lingerie collection and that he experimented with both.

"Why didn't you tell me?"

"I'm telling you now by showing you the results," James replied with a prideful smile.

"Were you wearing your mother's perfume last week?"

"Yep, and her body lotion," James grinned, "Did you like them?"

"Oh, yeah," I confirmed, "The scent and your shaven legs drove me wild."

"I had to do some maintenance today," James chuckled, "Didn't realise how quickly the hair grows back."

We kissed some more before James started to undress me, discarding them all around the loungeroom.

"There's that lovely cock of yours," James breathed before pushing me onto the couch.

He crawled between my spread legs and took my twitching cock deep down his throat. I almost exploded there and then. I was lightheaded and already perspiring. It took a Herculean effort to keep it together watching James as 'Jane' apply his expert oral skills and hearing him grunt in satisfaction.

I was being pampered. James spent considerable time sucking my cock, licking my balls, biffin before demanding access to my arsehole. I readily complied and flipped onto all fours resting against the back of the couch.

James had never rimmed another person before meeting me. I taught him how to use his tongue to pleasure the bung. He took to the task with youthful relish and quickly became accomplished, his tongue rasping over the surface and the tip stabbing the aperture. A natural bottom, I encouraged James to digitally finger my hole, but he displayed an unusual reluctance.

Today, however, it seemed his inhibitions were thrown to the wind. James had the courtesy to ask my permission first.

"Fuck yeah!" I replied, "Go for it."

Thus encouraged, James began tentatively at first but after reading the signs of my body quickly gained in confidence. He inserted a finger, commented on how tight and warm the hole was, and slowly began fucking me with it.

"Wank my cock as well," I hissed.

The combination of sensations was incredible, and I considered letting myself go but decided to wait for the main event.

"Has your mother got any lube?" I asked as James' saliva began to dry up.

"Sure. Do you want me to get it?"

James returned in a moment and greased up my arse before reinserting his finger.

"That feels much better," I moaned, "Try a second finger."

It took several goes but James got two dainty fingers inside me. We changed positions with me lying on my back with my legs in the air.

"Stick your fingers back in," I ordered, "I'm going to come any moment."

Under such pleasure, I could hold back my orgasm no more. James increased the tempo and pumped me hard.

"Open your mouth," I said, "Stick your tongue out."

James was moaning as loudly as me, anticipating a plastering which was delivered in short order. Just before coming, I grabbed James' wrist and jammed his fingers deep inside me. My cock erupted, lobbing ropes of thick sperm across James' feminized face, some landed in his mouth, but this was a proper pornstar cumshot.

"Fucking, yes!" He giggled girlishly.

When the primary orgasm subsided, James took my deflating shaft into his mouth and sucked the last drops out of my pee hole, triggering a diminishing series of pleasurable spasms. He sat back and eased his fingers from my pucker.

Sitting back, he sucked the fingers dry and complimented on how tasty my arse was before scooping the cum on his face into his mouth and swallowing and showing me an empty maw.

"Love the taste of your come."

I pulled James' sperm-splatter face to mine and kissed him furiously.

"So do I!"

We took a break, enjoyed a beer, before James gave me a tour of her mother's collection which was indeed impressive. One particular toy caught my attention, a set of anal beads. Sniffing them, they had been recently used and this caused a twitch down below. James' mother was stunning beautiful, judging by all the erotic photographs adorning the walls of the bedroom.

"Have you played with these?" I asked James.

"No, not yet" He replied, "Did you want to?"

"If you're up for it?"

James grinned and nodded in reply. We went back to the loungeroom, and James laid on the couch in the same position I had been not long ago. I grabbed his cock by the hairless back and began throating him. Simultaneously, I toyed with the butt plug, teasing James by partially withdrawing it before letting it go and watching it snap back into place. Each time, I withdrew the plug just that little bit more so as to stretch the muscle.

Eventually, I withdrew the plug and asked James to spread his cheeks. The beginning of a gape was present much to my satisfaction. Grabbing the lube, I spread a little over the reddened hole and told James to turn over.

With his girly arse high in the air, I grabbed the anal beads and gently inserted them. James was purring in satisfaction. Each bead temporarily formed the aperture open before snapping shut once it was inside.

"How does it feel?" I asked after the last one had been eagerly swallowed.

By now, I was fully charged for a second round of fun. After inserting my finger in the plastic ring, I pulled the string taut and grabbed James shaft, wanking it gently. His body was completely relaxed and he enjoyed the sensation of having the balls slowly withdrawn.

"I'm so ready to fuck," James breathed after the last ball exited his rectum with a satisfying pop.

"Me too," I said, "But first, insert the plug up my arse."

Bending over and spreading my cheeks, James applied some lube and gingerly inserted the metal toy.

I enjoyed the sensation of being stretched and filled with a foreign object. It seemed to jump start my cock to an extra level of hardness.

After applying lube to my cock and his arse, James ordered me over to a chair by the dining table. I slumped in it while he straddled me, his high heeled feet planted either side of me. Grabbing my cock by the base, James directed the tip to his relaxed bung and sat down on it. Unlike saliva, real lube aided penetration and James observed no pain as he sank down on my meat. This time James rode me hard, his dick slapping against my tummy and his fake tits in my face.

"Your cock feels so good in my arse," James panted.

I agreed readily, grabbed both cheeks and spread them wide. Placing a finger on my shaft, I felt James' pucker slide up and down with hard deliberate strokes. Once he had a comfortable rhythm going, James played with his cock before full-on tugging it.

"I want to come with you," He pleaded.

"I'm pretty close," I replied, slamming his bubble butt onto my cock.

"So, am I."

Minutes later, I could not hold back and let loose my second load deep inside James' shitter with all the force I could muster. James threw his head back and slammed his cock. As my orgasm subsided, James unleashed a monster load that covered my chest and hit my chin.

We agreed that both orgasms were amazing. Dismounting me, James leaned in for a kiss and rubbed his sperm into my chest before insisting that we suck each other's cocks.

Laying down on the kitchen floor on our sides, we eagerly took the other's deflating cocks in our mouths and gently sucked on them. James' cock tasted of cum and lube while mine was arse flavored.

Thoroughly satisfied for now, we decided to engage in some golden fun in the bathroom before cleaning up. I tried to keep the toy in me for as long as possible, but James insisted on returning it to the toy box.

For the rest of the night, we ate pizza, drank beer and watched movies. James, after defeminizing, insisted I stay the night. We slept together in the guest bedroom, looking forward to what antics Sunday might bring.