Michaels Story

By Beaumonte Bill / Oral Guy 2000

Published on Aug 2, 2015

Transgender

Michael's Story (part 8)

Cheryl Marie was a lovely girl I met in Cincinnati a number of years ago. Sadly, her life was cut short when she was hospitalized and died from pneumonia acquired there. Parts 1-7 of this story are exactly as she wrote it, except for a few spelling and grammatical corrections. This and subsequent parts I write in honor of Cheryl Marie – I only wish she could have written it and seen if published.

––––––––––––––––––––

When I arrived home Patti was there. She wasn't about to wait for a phone call.

"So, how did it go?" she asked, before I could even greet her.

Words were probably unnecessary, since my smile was so broad, but I replied, "Very business-like, but I think it's moving on from there!"

"Moving on to where?" Patti countered.

"He's asked me out on a date tonight!" I responded.

"A date?" Patti asked.

"Well, sort of," I said, "but we are both pretending that it's just two co-workers, but it feels to me like a lot more! I hope it does to Michael as well."

Patti smiled and continued, "then we better pick something extra special for you to wear tonight!"

With that we went inside and searched through my closet.

I had a couple of hours before Michael was due to pick me up, and I hoped I could be ready by then. I probably should never have called it a "date" because Patti now took things to a whole new level. She selected one of my best blue dresses and heels that looked like I was asking for it.

When I protested, Patti said, "Why on earth do you have these things if you didn't intend to wear them?" Good point.

Patti continued, "I want you to be ready for whatever comes along tonight. This is your first time with a man (except for the lunch you just had) – are you mentally prepared for him to kiss you? – how does the very idea of being kissed my Michael sound?"

"I've been thinking about it ever since he called me!" I reported, "I'm a little scared about it, but I kind of wish he already had. I don't dare make the first move, but don't want to let him get away without a first kiss."

"In that case, you better be prepared," Patti replied, opening her purse and tossing a couple of condoms on the bed.

"Patti!" I shot back, "you make is seem like I'm some sort of slut!"

"You are just a human being with feelings and desires like anyone else," Patti returned.

"I've thought about men – quite a bit – but only in a romantic way – not sexually," I explained.

"You know darned well that for most men romance is just a step away from sex," Patti continued, "so if you get him started, don't be surprised if his judgment isn't severely impaired."

"I want to interest him, not arouse him," I said, "but I'm not sure how to moderate his passion if he does get aroused. I'm curious about love making, but afraid at the same time."

"That can be a problem, especially since you would be receiving him anally," Patti responded, "many men are not very gentle once they are aroused – just make sure you don't let him in without protection – doctor's orders!"

"I can't imagine my letting him in on a first date," but if things continue I would have to eventually concede to him."

"Well, if you need to relieve his tension," said Patti, "you can always give him a blowjob."

"Strange as it may seem," I confessed, "I've never even thought about that. What do you think of it?"

"I hope you won't be forced into it – some guys are really insistent," Patti explained, "but if you like the idea of it, it can be really enjoyable to both of you. Of course you will need to be ready for him to cum."

"In my mouth?" I asked, "I hadn't thought about that either. What is is like?"

"Well, it's kind of an acquired taste," Patti said, "it will probably be very different than anything you have ever tasted, and if you enjoy sucking him, you may develop a liking for his semen. If you don't like the taste, it can be gone in a quick swallow, of course."

"Patti, you are a pretty earthy gal!" I said, "but I suppose I will soon be much less naive than I am now."

"No doubt," agreed Patti, helping me choose undergarments, "here, make sure you wear this push-up bra."

I really loved the push-up bra. I had been on hormones for eight months and had begun to grow small B cup breasts. The push-up bra made the most of what I had. The dress Patti had picked would reveal me nicely.

Patti and I shared a bottle of wine, but she left shortly before Michael was due to arrive. As I sat waiting I thought about kissing him, and about blowing him. I really wanted to end up kissing Michael a lot, and thought that I might be willing to blow him, but not as a quick way to relieve his passion. I knew that most men had sex on their mind most of the time, and Michael was a very studly guy, so I resigned myself to simply making the best of things.

Michael arrived and I greeted him at the door, offering some of the remaining wine. We sat on the couch and his eyes were all over me – and I loved it!

"I wasn't sure you would agree to go out with me," Michael said.

"I'm frankly surprised that you asked me," I replied, "but I'm really glad you did."

"He took me by the hands and said, "Cheryl, you are incredibly lovely – I had tried to imagine how you would look, but I never imagined that you would look so nice!"

I blushed, quite obviously. I wondered if Michaels imaginings were really fantasies, and began to envision him pleasuring himself while thinking of me. It sure is a good thing he wasn't telepathic!

It was time to leave, and Michael walked me out to his car. Before I could open the door he reached the handle and opened, saying, "allow me, my lady."

That was wonderfully romantic of him. I wasn't at all surprised to find that he was such a wonderful gentleman, but I had to continually remind myself of his "pants python" lurking out of site.

We had a nice conversation as we drove to Dayton. Along the way, his hand brushed mine, and I made sure not to flinch. Several minutes later his hand rested on mine and I turned and smiled. He smiled back and said my hand felt nice in his.

I told him that his big hand felt very nice as well.

I wanted to say more to him, but didn't want to seem too eager.

"Michael," I said, "I have never been with a man before you, and I am terrified and excited at the same time. I know this sounds dumb, but I want you to know that if I seem awkward it's because I'm in very unfamiliar territory.

"It's unfamiliar to me as well," Michael admitted, "but if we are willing to overlook a few mistakes, we can both have a wonderful evening."

"It's a deal!" I said, and he took my hand to his mouth and kissed it. It was a very favorable sign, but I hoped I would get more of a kiss than that – but the night was still young.

We arrived at the Italian restaurant and went in. Michael made a point of opening the doors for me and helping me with my chair – I could get accustomed to this kind of attention!

We sipped a nice red wine while studying the menu. This was a family-owned restaurant – not one of the big franchises. Michael told me that the food was fantastic and that I would love the salad. Soon a round loaf of Italian bread arrived along with a large bowl of salad. The waiter poured some olive oil on a plate of herbs. He took our orders and left us to enjoy each other's company.

When our orders arrived we enjoyed the food, which was every bit as sumptuous as Michael had described.

We talked about work a bit, then I changed the subject and said, "I have a lot on my mind, and I want this night to be special, and I want it to be a night we will remember fondly, without regrets."

"I want that also," said Michael, "so what is on your mind?"

"We are co-workers, and I don't want this to ruin a great working relationship," I said.

"I only want things to get better and better," Michael responded, "I hope I wasn't coming on too strong – to I need to back off some?"

"Oh no," I replied, "not at all – I don't know why I even brought it up – I suppose this is awkward for both of us."

"A bit," Michael said, "but I intend to treat you with respect, and hope that we can just enjoy this night."

Our meals arrived and we both enjoy our delightful Italian cuisine. After dinner we walked to the car and Michael continued to treat me royally.

–––––––––––––––––––– To be continued ...

Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)

Please support this website by donating to nifty.org

Next: Chapter 9


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate