Pleasuring Pamela

By Beaumonte Bill / Oral Guy 2000

Published on Jun 12, 2016

Transgender

Pleasuring Pamela (part 1)

A lot of guys like Tgirls and CDs because they see them as "easy" – good for a quick lay or a blowjob. Some of them are sluts and want that too, but some just want a normal relationship. I enjoyed giving the girls I dated a wonderfully shared experience. I was about to encounter an entirely different sort of experience.

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Pamela contacted me first on Yahoo Instant Messenger. She is a Tgirl, which immediately caught my interest. I have been dating CD and Tgirls for a number of years, and prefer them over any others.

Pamela: "Hello, I'm Pamela and just read one of your profiles."

Me: "I'm Bill, and I'm afraid you have me at a disadvantage."

Pamela: "I'm a Tgirl who is tired of guys who just want a quickie. I like what I've read about you being a gentleman, if that's really true."

Me: "It is, but feel free to ask me anything that you like."

Pamela: "You said that you are neither a dom nor a sub. The only men I know who aren't just trying to get off are subs."

Me: "Then perhaps you should get to know me. Do you currently have a boyfriend?"

Pamela: "I've never had a real boyfriend, but do have a few subs who serve me."

Me: "Are you looking for another sub?"

Pamela: "No, I'm looking for a real boyfriend – one who will put my pleasure ahead of his, and treat me like a lady."

Me: "Perhaps we should meet and see how it develops."

Pamela: "Maybe, but a few more questions. Does your 'oral_guy' ID mean you are good with your mouth?"

Me: "I am, but I urge you judge for yourself."

Pamela: "What are your oral limits?"

Me: "No limits – I'll kiss you anywhere."

Pamela: "Anywhere? Really?"

Me: "Absolutely!"

Pamela: "My ass?"

Me: "Especially your ass!"

Pamela: "Why especially?"

Me: "Because Tgirls are very anal-erotic, and rimming drives them wild!"

Pamela: "Then I look forward to you driving me wild."

We continued to chat and I was delighted to find that Pamela lived less than 50 mile from me – a welcomed change when most people on the internet are so very far away.

Pamela told me that she loved receiving oral but didn't like giving it, nor would she be open to intercourse, but assured me that I would be cumming in many ways if I took good care of her.

She said she would email explicit pictures of her, and asked that I print them and cum all over them, sending her a picture of her cum-covered pictures, so she would know that I came looking at her.

I went to my email and found she sent me three pictures, one attractive face picture, one with her ass spread wide, showing her tender pucker, and another showing her hard clitty. I had no difficulty getting aroused, and quickly printed out the pictures and slipped them into clear plastic slip covers.

I jacked off as directed, shooting my load on her pictures. I snapped a picture of each of the cum-covered pictures and emailed them to Pamela.

After she recieved them we chatted more and agreed to meet tomorrow evening at her home for a dinner date. She gave me her address and we concluded our chat.

The next day I found myself thinking about Pamela most of the day, and was glad to finally leave work and go home to change for our date. I prepared as I would to meet a very special lady. Our chat had been rather earthy, but today we meet as lady and gentleman.

I arrived at Pamela's home and she welcomed me in, offering me a glass of wine. She was dressed in a lovely blue dress that accented her femininity wonderfully. She smiled beautifully, and I found myself staring alternately at her lovely smile and her ample cleavage.

We sat on the couch and I began, "Last night you set some of your conditions, now here are mine. While I am not a dom, I am a man, and will take the lead, but will be sensitive to your needs. As a gentleman I will treat you as a lady, and I expect you to act accordingly."

Pamela smiled and said, "Your doing well so far – please continue."

I said, "I know you are capable of doing things for yourself, but I will open doors for you, help you with your coat and your seat in restaurants, and I expect you to patiently wait for me to do so."

"Oh, I like a man who takes charge," she replied, "Not like those wimps I've been seeing. I agree to your terms, kind sir!"

We departed for the restaurant, an Italian steak house. As instructed, Pamela waited in the car for me to open her door and she took my hand, assisting her exit. She held my arm as we walked to the restaurant, and waited for me to open the door for her.

We were led to our seats and I helped her with her coat and her chair.

"Did you see that woman watching us?" Pamela asked, "she was nudging her man, probably asking why he didn't attend to her as you've done."

"If he's smart he won't tell her the real reason." I said.

"And what would that be?" inquired Pamela.

"Because you are much hotter than she is!" I answered.

We both laughed and Pamela added, "I can tell we are going to have a wonderful time together."

I ordered for the two of us and we enjoyed a wonderful dinner. I think it may have been the first time that Pamela was ever treated like a lady, and she really warmed up to it!

After dinner we left the restaurant and found the weather was fair – cool, but no wind, so we took a walk along the river. At first Pamela held my arm, but soon her hand dropped and took my hand in hers. I saw that as a good sign, and we walked hand-in-hand for a time. We reached an overlook by one of the piers and we stopped to just watch the lights on passing boats.

I was about six inches taller than Pamela, so even in heels she had to look up at me. I looked into her eyes and leaned to kiss her. She reached up and brought her lips to mine, parting to extend her tongue into my mouth. Our tongues danced together.

She pulled close to me and I put my arms around her. "Let's continue this at home," she said, and we walked back to the car.

On the drive back to her home, Pamela put her hand between my legs and aroused me. "If you are as good to me as I hope you will be," she said, "then I will be VERY good to you!"

We arrived at Pamela's home and she handed me the key to unlock her door – she was definitely getting into being my lady!

She led me to the living room and told me to take a seat while she changed into something more comfortable.

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

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

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Next: Chapter 2


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