Shemale Becomes Friend Ch. 04

She pulled out and lay on top of me and was very warm and loving. But at the same time my ring and insides were starting to hurt more and more and my regrets were growing with the pain.

That instrument of pleasure and pain that still throbbed behind me pressed along my thighs to my butt. I resented it. I resented her.

I could feel it inside of me even after it was removed. I could feel my insides vibrating in shock about my decisions and their contortions. I feared that I'd never feel the same.

Meanwhile she was so happy with herself. On top of me touching me possessively. Probably hoping she could finish. But, I was done. I needed to take a shower. I was afraid that I hurt myself or changed myself. I was even afraid of diseases or psychological changes.

And meanwhile, how did I cum so easily from her? How did I go so crazy? How was I begging for her to go deeper even though she was trying to be gentle? I needed to think. She wasn't here to hurt me. She liked me. It was all too much.

"Joline, I have to take a shower and clean up."

She rolled off of me gracefully and I walked to the bathroom. She followed.

I stepped into the shower. She followed. I felt a little guilty. Her hard on swayed upwards towards me with need. Need that I could not or would not fulfill, even though it filled me and made me cum, even though I was begging for it just a few short minutes ago as it stretched me and made me yearn for more. Her hard on bumped into my thigh and I hopped away to avoid it. I didn't look at her. I felt guilty and angry.

I turned on the water. She stood behind me. She touched my back lightly with her fingers, "Are you okay, baby?"

"Yeah." But, I was not her baby.

I turned on the water and turned around so that my back was facing the water. Joline smiled at me compassionately. I gently touched my lubricant covered behind and I cringed it hurt.

"Oh, I'm sorry baby. I really screwed up. I'm so sorry. I just couldn't say no to you."

"I know," I answered.

I continued to gently touch it. Slowly and carefully cleaning it. I looked at her and her penis was soft and drooping guiltily, pointing downward.

Joline didn't know what to do. I'd never seen her not glowing. She just stood there feeling very guilty.

I scrubbed. I used soap. I rubbed. I was finished cleaning myself. She watched. I turned off the water.

"Are you alright?" She asked touching my arm.

"I think so." I wasn't sure at all and I didn't sound like it. I've never hurt down there like that. I've never experienced anything like this. This is my body that was at stake. What happens if it's stretched out of shape. Does it recover? Was this natural?

"Max, I'm sorry I hurt you. Can I see it?"

"I don't know," I answered. She seemed genuinely concerned. But, for some reason I was now very private about it. This was a personal issue.

"Max, I might know a thing or two about this part of your body. Let me check you out. I'll tell you if there is a problem."

"Okay."

I went back to the couch and lay down. Back on my stomach again. She walked around still naked, still not hard, concerned. She touched my butt cheeks with her cool fingers. She gently pried them apart and then with one finger barely touched me on my ring. "Does this hurt?"

"No." I was wondering if it looked different after being stretched. "Does it look okay?"

"It looks beautiful," Joline enthused.

"Does it look stretched out? Does it have the same shape? It doesn't feel the same." I asked.

"Of course it's not stretched." She said with shock. "It looks just like it did earlier only it's just a little bit red and that will go away very soon. But, it's beautiful." She then held my cheeks and lowered her head. I didn't know what she was doing but she then gave me a single brief dry kiss right on my hole. I was very surprised. It felt nice. It actually made me feel better.

"I'm not that big, Max. And I was so gentle and we used the oil. And I only went in a few inches. People's bodies don't just lose their shape and form from sex. And I would never do anything to hurt you, anyways. I don't see any blood and I don't see any swelling or anything that looks extraordinary. And you are just as kissable there as everywhere else."

I didn't respond.

She massaged the area around my hole with her fingers. "Does this feel okay?"

"Yes."

"Max, the one thing that I think we should do is put a little bit more lubricant on you so that you are comfortable. You washed so much that it'll be try and irritated."

"Okay. I don't know though. I really hope that nothing got hurt deep inside of me. I'm sorry I'm so immature about this but I'm a little bit afraid."

She lay her hands on me and hugged my torso. "Max, I wouldn't be able to live with myself if I hurt you, but, I really don't think you are hurt. I wish I was smaller. But, what we did was perfectly natural and normal. People have been doing it for thousands of years. And don't forget that your body did respond to me. Your body loved how it felt at the time. You are sore now, but, I promise you'll feel as good as ever tomorrow."

She grabbed her bottle. She squirted some on her finger and rubbed it around my hole. It still felt good but it was also pretty irritated and I was not horny enough to respond like before.

"Max, I'm going to gently put a little bit on your insides and check you out a little bit more. If it hurts tell me."

I didn't say anything she took some more oil and squirted on me and gently pushed some inside. One of her thin fingers edged in. "You are so tight!"

It felt nice to know I was still tight. I don't know why I cared. I wasn't planning on ever doing that to myself again. And I am not gay. So why would I care if I'm loose. But, I was pleased. "Thanks." I tried to squeeze my ring of muscles around her finger with what energy it had, showing off my tightness.

"Oh, baby, you are cutting off my circulation. Let up!" She smiled, glowing, and I smiled too in spite of myself.

I felt a little bit more calm and figured I'd just let the evening go. She asked if I wanted to watch TV. And I said okay and she curled into my arm and we watched for a while. But, I didn't say much and was pretty passive and cold.

When the show was over she said, "Max, do you need a little bit of time to think and stuff?"

"Maybe,"

She kissed me once on the neck and wrapped her hands wrapped around me and said, "I'll see you for our run."

"Yes."

She walked out and waved and left me.

I was so confused. As soon as I left I thought I'd be ready to think about life. Wonder if what Joline did felt better than what I've experienced with women. But instead I was drawn to my bedroom to masturbate. I wanted to go and find a woman to have sex with. But, I couldn't wait. I just had to do it myself.

I stripped and went to bed and played with myself. But, although I was surprisingly hard, I barely felt anything and I was lonely. Very weird. I wondered if perhaps I'd already changed how I felt about sex. I knew this was crazy but I wondered if the nerves around my prostate and my ring became my primary outlet. I tried touching myself there even though it was sore. But that didn't feel like anything either.

I knew that I had to also use my penis on someone. I had to make sure that I could also enjoy penetrating and probing with my penis. I couldn't just go through life on my stomach passively receiving even though I could see that that would be a very tempting routine to fall into. I knew only one person that might just be available and I just sent her home.

I called her up, "Joline, How are you doing?"

"Good."

"Do you want to watch a movie tonight? I'm done thinking."

"I'll turn right around."

"I'm sorry," I said, "I don't know what we are doing but I want to do it well. You deserve better."

"That's okay. I understand."