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."
