Mary & Jazzy: Part 5 — Jazzy Tells All

It was some time before Mary was able to tell me the rest of the story about her grandson Jason and his/her magical weekend en femme. If you have been following along you know about how young Jason revealed to his grandfather, Martin, that he knew about Martin’s past dallying in transvestism or fetishistic crossdressing or whatever it is called these days and further revealed that rather than being shocked he had actually copied and enjoyed gaining sexual arousal through the stimulation of feminine lingerie.

One thing led to another as Jason revealed that he wanted to try a full transformation. That was arranged at Trading Faces. That led to a shopping trip, dinner out and a trip to the famous Parliament House night club. There the two had parted company as admirer Steve took an immediate interest in Jazzy, Jason’s chosen femme name.

Is this sounding like a soap opera parody to you? It was to me but then I only report what I’m told. Life is sometimes stranger than fiction.

Martin returned to his rented condo after sharing some safety advice with Jazzy and giving a stern admonishment to Steve, “take care of this girl or I will find you.” In fact as Mary he knew Steve and he knew Steve would respect Jazzy’s limits. Martin knew his grandchild Jazzy less well.

It was very early the next morning before Martin heard the front door open and the slight sound of a car driving away. He thought of faking sleep as Jazzy made her way to her room but curiosity got the better of him.

“So how was your evening?” asked Martin.

“Fine.”

“Just fine? Did he treat you well?”

“Yes, fine.” It seemed to Martin that some habits die harder than others. Jazzy was reverting to Jason’s style of communication. It’s way after midnight, he was thinking, perhaps Cinderella’s spell has been broken. If it was any consolation Jazzy’s outfit and makeup did not look too askew.

“I’ll tell you about it later. I’m really tired and right now. I have some thinking to do,” Jazzy replied.

“Do you want to talk about it?” The Mary in Martin was dying to chat about Jazzy’s first date.

“Not right now. I just want to go to sleep.”

It occurred to Martin that Jazzy might well have gone over a line she wasn’t entirely comfortable in crossing and now was having some regrets. He resisted the temptation to push. There would be time later.

“Take off your makeup before you lie down,” Martin called out as Jazzy entered her bedroom, “I don’t want stains on the pillow cases.”

It was just before noon the next day when, to Martin’s great disappointment, Jason, not Jazzy, emerged from his room. He was wearing jean shorts and his usual black rock band t-shirt. His long hair was pulled back in a man-style pony tail.

“Would you like something to eat?” said the grandfather.

“I’ll just grab some cereal.”

“Would you like a coffee?”

“Nah.”

‘Oh great,’ thought Martin, ‘I have the old Jason back.’ But he persisted. Giving Jason time to settle in with his cereal, Martin opened up, “so tell me about last night. Did my princess have a good time?”

“It was okay.”

“Okay? When I left you two seemed to be having a great time. What happened? Did Steve hurt you?”

“Look Grandpa, I appreciate your concern and I had a great time yesterday, Really, I did. It’s just that some things are not that easy for a guy to talk about.”

“Okay,” Martin replied, “I won’t push it but I’m here when you are ready and if Jason won’t want to talk about it perhaps Jazzy would.” Martin did not know what kind of reaction the last bit would get but he thought he would put it out there. ‘Jazzy’ was more than welcome in his household.

“Perhaps,” was Jason’s only reaction.

It was by then Sunday afternoon. As Jason rummaged in the kitchen Martin settled in to watch his football games and promptly fell asleep. Two hours later when he awoke Jason was nowhere to be seen. Jazzy was sitting in the chair next to him, sipping a beer.

“Oh, what a pleasant surprise!” said Martin, “it’s so good to see you.”

“You are right. It is going to be easier to talk about last night when I’m dressed as Jazzy. As a man I’m not very comfortable with what happened.”

Martin, and I guess everyone reading this, knew where this was going. “How so? Just tell me what you feel like telling.” Martin’s mind was racing. Did Steve rape her? Was there consensual penetration? He was pretty sure Steve would not have gone where he didn’t have consent. Did Jazzy give consent Jason later regretted? ‘That wouldn’t be a first in the TG world,’ he thought.

“First of all, let me assure you Steve was only a gentleman. He was very careful to compliment me and to treat me like a lady. He opened doors for me, held my chair and bought me drinks, perhaps too many drinks. We danced a lot including some body contact dances where he taught me to follow his lead which was pretty easy as I’d never learned how to lead.”

Martin thought to himself, ‘Wow, it is like pulling teeth to get a one word answer out of Jason but Jazzy is really opening up.’

“Then Steve suggested we get some air by going for a walk around the P-house grounds. We walked out to the lake and around the pool. We found a secluded spot to sit and finish our drinks. There were some people around but not many. Steve pulled his chair next to mine and put his arm around my shoulders. It felt so natural for me to lean my head on his shoulder. In my mind I knew we were two guys and I’ve never been with a guy before but this felt nice. Man or not, I liked that he was attracted to me or to my feminine self.”

“I’m sensing that wasn’t the end of it.”

“Hell no! Pretty soon his hand moved from my shoulder up in to my hair. It felt so nice to have his fingers combing through my hair as he looked me straight in the eyes. We kissed and kissed. Tender at first and then we both were trying to tongue each other.  I’ve never had anyone try to put their tongue in my mouth. I enjoyed it.” She paused.

“Gee, I think you’re starting to get this old guy excited,” Martin interjected, “Please go on.”

“Sorry, grandpa, please don’t think bad of me. I really don’t know what came over me but when Steve shifted his body position it left me no doubt that he had an erection and it wasn’t a small one.”

‘That’s my Steve,’ thought Martin but he said, “Did that make you feel uncomfortable?”

“I guess it should have but in truth if I hadn’t been so constrained by that gaffe I would have had one, too.”

“Did that surprise you?”

“Hell, yes. I mean I am used to being aroused by wearing lingerie but this was different. I hadn’t been physically aroused by the full transformation but seeing a man turned on by me and being nice to me; that was making me so hot!”

“What did you do?”

“What would you have done, grandpa, if you were me and it happened to you?” shot back Jazzy.

“I don’t know,” Martin lied again. He couldn’t tell his grandchild that Steve had also been his lover at least a half dozen times and every time he couldn’t wait for the first taste of Steve’s ‘manhood’.

“Well I touched him and was getting ready to go down when someone walking by said, ‘get a room.’ So Steve suggested we do just that and I agreed. In no time at all we were in bed together. He was naked but he let me keep on my dress. I mean I don’t think I’m gay but it felt so natural and wonderful to be having sex with that man at that time. He didn’t penetrate me and when we came it was pretty well together and in to our own towels.”

“How did you feel afterwards?”

“That’s just it. I didn’t feel as guilty as I often did after jerking off wearing mom’s or Sandi’s panties but I began to wonder about myself. I’ve always enjoyed women so why did I enjoy being with Steve. Am I really gay?”

“I doubt that. Let me tell you about something that happened to me when I was just a little bit younger than you are now. I’ve never told anyone about this but it happened. I had gone away to college in Ohio but I came home every summer. I wanted a summer job at the plant but those jobs were hard to come by. I pulled a few strings and one of the managers took me under his wing and got me on his staff as a special assistant. To celebrate my job he suggested we go in to the City for dinner and a show. We had lots to drink and we decided that rather than driving back we should get a room and stay over.  Long story short I woke up from my drunken sleep to find him slipping his head under my covers. I let him give me a blow job and when he came back from a bathroom break I went down on him. Out of the blue: I’d never thought of doing that before. When it was over we went  to sleep. In the morning we didn’t speak of it and on the way home we hardly spoke at all. We worked together but we never spoke of that night. In fact the next night I went out with your grandmother and we started on a path that would lead to your mother and uncle.

“The point is one night or one event does not define you unless you let it or want it to.”

“So the fact that I had sex with Steve doesn’t mean that I am gay?”

“That’s up to you to decide but what you told me about feeling aroused because Steve was aroused by your feminine image suggests to me that you were reacting to something completely different than being aroused by his penis.”

Jazzy sat silently.

“Look,” continued Martin, “there is a saying that you can build a thousand great bridges and never be known as Jason the great bridge builder but suck one cock. . . .  Don’t believe it. You are who you are and who you are is up to you to decide.”

Jazzy smiled.

“I don’t know where you are going to take Jazzy, whether she will be an important or an occasional part of your life but one thing is for sure Jason and Jazzy are both certainly welcome in my life.”

Jazzy got up from the couch, came over to her grandfather and gave him a big hug. Martin hugged back. “You know,” he said, “since you were a little boy that is something I’ve not been able to do with Jason.” He paused a second then continued, “oh, of course you know.” They both smiled and hugged again.

In a few days it was time for Jason to head home. In those few days Martin and Jazzy visited Epcot, went zip lining, horseback riding and to a dinner theater show. If they got any looks it was because there was a curiosity about the relationship between the older man and the young lady who kept grabbing his arm.

They also had a long chance to talk grandfather to grandchild. Jazzy/Jason expressed a real desire to turn his life around. He determined to put Jazzy aside for a while to make a success of his life in the body he was given before exploring options to bring Jazzy back.

Martin agreed to keep Jazzy’s outfits safe for her and to welcome her if she wanted a return visit. Martin had already decided that when, not if, Jazzy came back she would meet Mary.

“When will that be?” I asked Mary.

“I don’t know but it can’t be soon enough for me.”

“Well remember I have the exclusive book, movie and TV rights,” I concluded as we both laughed.

That brings us up to date on Jazzy. Jason is busy working. He is actually in some demand in the high tech programming field. Apparently he has even cut his beautiful hair in an attempt to present a more mature image in the workforce. He is back together with Sandi. They seem intent on making Mary a great grandparent.

Will Jason be able to submerge Jazzy? Will he tell Sandi about her? What happens when, not if, Jazzy comes back to the surface? Only time will give us the answers to these questions.  

But I’m not finished with Mary. You may have noticed an inconsistency between her ‘one and done’ gay sex experience she revealed to Jazzy and her active sex life as Mary. I want to talk more with her about that. Her reasoning seems unconventional but I think we may find her views interesting.

I must mention one other thing for those who had been asking “where are the photos?” I hate to be a tease but with Jason going ‘straight’ Mary has asked that I not share any of the photos she had sent to me, nor would she provide any others. I remain one of the few in the world with visible proof whether or not Jazzy really existed.

Tags: crossdressing, featured, Identity, Linda Jensen, Martin and Jazzy

Category: Transgender Fun & Entertainment