Marsha Under Cover

By Beaumonte Bill / Oral Guy 2000

Published on Sep 18, 2015

Transgender

Marsha Under Cover (part 9)

How does a straight man deal with a truly beautiful cross-dresser, even when he knows her secret? I hope you enjoy this work of fiction.

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We awoke the next morning in an especially playful mood. We didn't have any obligations until after lunch, so we could spend the morning enjoying each other. I decided to introduce Marsha to some new pleasures.

As we kissed, I gently squeezed Marsha's nipples and she moaned with pleasure. I took one of her nipples in my mouth and sucked, then moved to the other. I could see that she was becoming aroused.

I reached into the nightstand drawer on my side of the bed and took out a pair of nipple cups, and some lotion. I applied a drop of lotion to each cup and smeared it along the perimeter. I squeezed each cup and applied them to Marsha's nipples. The vacuum held them in place while giving a gently tugging at the nipples.

"What are those?!" asked Marsha, "it feels like you are still sucking!"

"They are nipple cups," I said, "while giving you pleasure they will also enlarge your nipples if you use them regularly."

"Heck, I'll used then all the time!" exclaimed Marsha.

"Not so fast," I cautioned, "You must only wear them for 20 minutes at a time. You can use them several times a day, but only for 20 minutes at a time – and you must promise me to NEVER where them to bed!"

"Why not?" she asked.

"Because if you fall asleep with then on you will wake up with VERY SORE NIPPLES," I explained, "I've read where some girls actually had blisters on their nipples, so please be careful in using them."

"Ok, I will," promised Marsha.

They were a hot pink color and looked really sexy on Marsha. I had her get up and look in the mirror, and she really liked the appearance.

"Ready to try something else?" I asked. I reached into the nightstand drawer and took out a vibrator and a dildo.

"You are full of surprises today!" she said, "are your getting ready to de-flower me?"

"Not exactly," I said, but I want you to learn more anal pleasures so that when you do give me your virginity, it will be very pleasurable for both of us.

"I'm willing to give it to you, Bill," she said, "why don't you take me right now?"

"Patience, my dear," I said, "giving your virginity to me is not just a matter of my plunging in and having my way with you! I want it to be one of the best experiences of your life, and one you will fondly remember forever. Anal can be very pleasurable, and I want you to learn that first."

"Ok, I'm eager for you to teach me," she said, with a mischevious grin.

I spread Marsha's legs and put some gentle lotion on my finger, pressing it to her rosebud. Marsha inhaled abruptly, and then smiled.

"I'm pressing against you," I said, "but you are tight – that's natural because you are accustomed to things coming out, not going in. There is a very fine line between wonderful anal pleasure and intense anal pain, and I want to keep you on the right side of that line."

I continued, "I can force my way in, but it may hurt. Just relax your muscles and you will be inviting me in, which will feel much better.

She relaxed and my finger tip slipped in, and I worked it in and out. How does that feel?" I asked.

"Wonderful!" Marsha replied, "keep going."

"The key is relaxation and plenty of lubrication. KY jelly is often used, but any gentle lotion will work. Be careful because some hand lotions are not gentle, and will sting on your sensitive areas."

I withdrew my finger and put more lotion on, and then inserted two fingers, working them in and out. I've had two fingers in you before, and you really liked that. Once you are accustomed to this we'll take the next step."

"Three fingers?" she asked.

"We could," I responded, "but I have something else in mind." I took the vibrator and lubed the tip. After withdrawing my fingers I placed the tip of the vibrator to Marsha's rosebud and said, "now relax, like before."

Marsha relaxed and the vibrator slipped in. "This vibrator has a loop of cord at the bottom. If you feel it is going in most of the way, make sure you hold onto the loop. It isn't likely, but if it does go in all the way you can pull it back out."

"Marsha dear," I said, "please NEVER put an anal toy in all the way. Some don't come out easily and I don't want you to have an embarrassing and expensive trip to the emergency room!"

Once the vibrator was in about half way I flipped the switch. As the vibrator buzzed, Marsha nearly jumped out of the bed. "Oh my God!" she said, "that's amazing!"

"Yes it is," I said, "and that's part of why I want you to learn to truly enjoy anal before you give yourself to me."

I handed Marsha the dildo and she looked it over. It was about my size, which is why I bought that size for her. I said, "When you feel ready, you can practice with this. Remember to relax, use plenty of lube and go slow! The balls at the bottom of the dildo are not there to be `anatomically correct' but to keep it from going in all the way – it is safe for you to sit on, if that is comfortable for you. When you get to the point where you can take this easily, and enjoy it, then you will be physically ready. When you are also in the mood, we can join in love."

"You stay here and enjoy the vibrator and I'll order breakfast from room service," I said.

Before I stepped out of the bedroom, I brought a wet washcloth from the bathroom, and said, "This is a good thing to keep handy also."

I watched Marsha in admiration as she worked the vibrator in and out of her while she was fully erect. As I stepped out I said, "Let me know when you are ready for me to bring you to climax."

Marsha smiled and returned to her bliss.

After ordering breakfast I returned and Marsha said, "I think I'm ready for you."

I took her lovely petite clitty into my mouth and sucked her. She was ready to cum and in less than a minute gave me her juice, which I now thoroughly enjoyed.

She fell back onto a pillow, seemingly exhausted – after over 20 minutes of arousal, she needed a rest.

I removed the vibrator and cleaned her up.

I gently removed the nipple cups and washed them and the vibrator in the bathroom sink.

I kissed Marsha gently as she lay there. "You are so good to me," she said.

"I've never had anyone like you in my life before," I said, "and I really appreciate you."

There was a knock at the door and I went to receive our breakfast, closing the bedroom door.

After signing for the breakfast and giving a tip, I closed the door and told Marsha that breakfast was ready. She was in the bathroom, but when she emerged she had touched up her makeup and looked as beautiful as ever.

We dined on huevos rancheros, a southwestern/Mexican style of eggs. After finishing breakfast, we sat on the couch with our coffee cups. She said, "I have something I want to ask you, but I'm not sure just how to ask."

"Well, just say it," I said, "if it comes out wrong, we'll just take it from there."

"Well ... I really like the anal ... but remember when you kissed me, 'back there' several times?" she asked.

I was getting the picture – she was too lady-like to ask me about kissing her ass!

"Yes, that's called rimming," I said.

"Well, why did you do it?" she asked.

"Some people find it very pleasurable, and I wanted to do something really nice for you."

"Nice is an understatement!" she declared, "it was fantastic! But who would even think of doing such a thing?"

"Well, I didn't invent it," I said, "but I did like the way you responded to it."

"Yes, I loved it," she said, "but it seems like such a dirty thing to do!"

"Well, you were wonderfully clean, dear," I responded, "so it was very nice for both of us."

"But what if there is a time when I'm not clean when you do it?" she asked.

"Well, you will be clean when I'm done!" I responded.

"YUK!!!" Marsha exclaimed.

"Well, I guess you'll have to see to it that you are always 'kissing clean' for me." I said.

"I will," promised Marsha

We showered, dressed and got on with our day.

–––––––––––––––––––– 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 10


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