Shemale Becomes Friend Ch. 03

After Joline left, I was extremely horny and could barely sleep.

I knew that this was getting out of control. I made the decision that being with Joline wasn't the life that I was looking for, but, I couldn't get the eroticism of being with her out of my mind.

I counted the days nervously till our next run.

Joline acted like everything was normal. A typical run. When it was done she asked, "Would you like to go to the cafe?"

I said, "Sure."

Then she said, "Or we can just go to your place and get some water there and get cleaned up. Then we can stretch a bit and have a massage."

My heart jumped. She was watching me and smiling mischievously.

I thought for a moment and wanted to say, no, but I couldn't do it. "That sounds good," I said.

We went to my house and showered. First Joline and then me. She still acted like normal.

"Are you ready for your massage?" Joline asked greeting me as I left the bathroom in my towel.

I nodded lay down with my towel still wrapped around my waist. She came to me and touched me. She started worked my body and legs. Briefly my shoulders then my back. Her hands were cool and smooth. Then she reached the towel. "This will just get in the way." She pulled it off.

Then she stopped and went through her hand bag and said, "Look what I brought," and she pulled out her oil and dripped it all over me as she worked my muscles. She then got to my butt and she changed her massage subtly to an erotic one. Her finger nails light and then pressing into my flesh. "I have an important question for you Max. Do you want me to work your hamstrings, butt, and back some more, or do you want to turn over."

I was hard and getting harder and realized that perhaps I should just stick with this massage unlike last time and so I said, "I think I'll stay."

Joline said, "A very good choice."

She then squirted more oil on me and continued to work my body. But, now the deep tissue massage was over and instead I was treated to a lighter and harder and more erotic massage. I was being stimulated as much or more than I was being massaged. She reached for my butt again and used her nails on me and I writhed but she continued until I groaned from the intensity, then she stopped. "Is that too intense for you?" She asked.

"Maybe a little bit."

She then touched me lightly on my butt and put more oil there and spread my cheeks and rubbed some oil inside of me. "I bet you've never been massaged here." She said as her fingers circled around my rim. I couldn't believe I was letting her do that and I couldn't believe how good it felt. She added more oil and circled even deeper and said, "I'm having so much fun massaging you. I love your body. Do you like this?" She asked as her fingers circled my ring slowly playing with going inside but never entering?

"It feels good."

"Good."

She then worked her way up to my upper body and covered me with her body and whispered in my ear, "How are you feeling?"

"Very well."

She then got off of me and took off her clothing. Her long penis swayed in the air by me and I didn't say anything and she didn't say anything. I just watched, mesmerized by her.

She then went into her purse and took out a condom and said, "Look what I have," with that same mischievous smile.

I had a burst of excitement in me when I saw her holding the condom. It felt like a mini orgasm.

I didn't say anything. She didn't say anything. Where was this going?

She then opened it up. Her eyes never left me. And she rolled it on her penis.

I didn't say anything.

She then said, "Now back to your massage."

She started with my feet and tickled me a bit and worked her way up lightly till she reached my butt and she touched it lightly around the edge of my ring and then massaged it a bit and spread my cheeks wide and squeezed my butt cheeks with her hands. "You are so adorable." she said as she worked up my body kissing me on my back. Then I felt it. Her penis touched my butt. I didn't say anything. I just held my breath. I knew what was about to happen.

"I'm going to treat you so well. This will be so gentle. I promise."

I didn't say anything. My heart was thumping in my chest.

Her penis moved forward until it was pressing against my well stimulated ring. It then began to enter. It didn't hurt at all at first until a few inches and then she felt the resistance and pulled back and pushed forward again. "Mmmmmmm, Baby," She said, "You feel so good." She pushed in and out. It felt good but wasn't as intensely pleasurable as her fingers. Then she went faster. She was breathing heavily and moaning. Then she penetrated me a little bit harder and it felt like I came but I didn't. "Is that okay baby?" She asked.

"Yes. Go deeper."

She continued and pressed a little bit deeper into me and just waited for it to drive in bit by bit. She started kissing me on my neck my face and ears. I could hear her breathing heavily.

She then pulled out and started pumping in to me. "Ooooo, Baby, you are so fine."

It hurt a little bit and I said, "Deeper." I don't know why but I felt like my body needed it, she meanwhile seemed content to just pump into me but not all the way.

She pushed a little harder and it hurt and I groaned and said, "Stop."

She said, "I'm sorry, but, you did say deeper."

"I know."

She then continued to pump into me again and again only with those first few inches. It felt good. Then she slowed down and pushed in slowly again. It felt so intensely good. I hoped it would last for a long time. "Deeper," I requested.

She said, "your decision," and she pressed harder, it felt very hard, my whole body was stretching to accommodate her, and it hurt, but, I didn't say anything. Then she slowly pulled out and played around at other depths. I just submitted to her as she groaned and moaned and touched me and penetrated my ring. I could feel my insides being massaged and stretched and it ached in a nice way, but, it also hurt. I was so horny that I didn't care. I was lost in this experience.

"You are doing so well. I'm so proud of you," She said. And then she changed her angle and went in and I groaned. So she did it again faster and I groaned again and she groaned and squeaked. Then she stepped it up pumping into what felt like my muscle that controlled orgasms, perhaps my prostate, and I immediately started to cum. I grunted lightly. She pressed even harder. So hard that I groaned with pain and pleasure. And my groans just encouraged her to go faster and harder. It was so intense that my eyes teared from all the sensations. But, she didn't stop and the orgasm slowly dwindled but she was still there exploring and stretching me out as the pleasure slowly went away. Then I realized that it hurt, and now that I was spent, my feelings changed. I was done.

I said, "Stop. It hurts." She stopped although she didn't take it out.

"I know. Baby. I'm sorry. But, I'm so proud of you that you came from me. That's so hot. I wish you lasted longer so that I could give you even more pleasure."

I felt a little bit guilty. She was still hard. And my tone wasn't very nice.

She lay on top of me not pulling out but still not 100% in and just cuddled me for a few minutes. Then she started pulling out slowly and I felt so relieved. Then she pushed in again.

I said, "Ow. You have to stop. It hurts."

It didn't really hurt that much. It was just sore. But, I felt like I was done.

She said, "Okay. I'm sorry. This is for you. But, I do admit that I was getting close and maybe I am just too eager for you. A girl can lose her head a little bit when she's so close to getting off in a cute guy like you."

I said, "I know but it hurts."

She said, "Okay," and stayed still inside of me just holding me for a while as I just lay there not knowing what to do, thinking about what had just happened. I could feel her penis inside of me, still hard. I felt like I could feel her heart beating through her penis or perhaps it was mine. I was so achy and she was so hard and patient. I was very conscious of her unmoving penetration. It was there. Every so often I couldn't resist squeezing it. It was the least I could do now that I made her stop. But, my insides were too tired and worn out even to do that. I was done. She was still hard and ready.

She got me off. And here I was just stopping her cold. Perhaps she could've just gone slowly and I would be fine. I felt a little guilty, but, I had something in me resisting. It was one thing to receive anal sex when I was so horny. Quite another now. The pain and the thoughts combined were too much.

I stayed there and thought and felt her. And she lay on top of me quietly holding me and occasionally hugging me. She must've been reluctant to pull out and end this. And I was trapped in the experience unable to act.

Then she slowly pulled away, even that hurt a little bit in a nice way. Even though she wasn't all the way in, I could feel the gentle progress. I could feel my body struggling and aching to keep her. When she was out, I immediately felt abandoned, unloved, worried, and at the same time very aware that I'd violated yet another one of my conservative taboos.