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Shemale Becomes Friend

By: refinedexperiences



Last month I was working a dating site with little satisfactory results when I finally got a response from a girl. She was 6 feet tall and blonde. She seemed to have a nice figure and seemed very very athletic. I played basketball in high school and am pretty trim, although all I do nowadays, as an adult in my 20s, is go for runs on the weekend. Still, I love an athletic girl. And who doesn't love a 6 foot tall blonde. Sweet.

We corresponded back and forth with two emails and she seemed excited to talk with me.

She wrote, "You are just my type! But you need to be aware of the fact that I'm a transsexual. I hope that's not a problem. I'm an awesome girlfriend."

I was a bit disappointed because I was looking forward to trying to build a relationship that could result in children. I'm a little bit traditional. And she was proposing what I viewed as a long term lifestyle change.

So, I wrote to her a white lie, "Sorry, last night I had an awesome date with another girl and now I am going to focus on making the most of it. So I'm off the market."

She responded, "Really? I need to know the truth." 

I said, "Yup, for real."

She followed up and said, "That's understandable. Good luck with that. But, we both did say we need a running partner, so if you want, we can go for a run."

That sounded reasonable. I didn't really need a running partner, but, I saw no harm in a run.

We met by the park. She was dressed in a track suit. Looked fine. No one stared. No drama. We completed the circle. She kept the pace up.

She asked, "You want to go to the cafe?" 

I said, "Sure."

We ate. She seemed pretty cool. She touched me once or twice with her very long fingers on my arms and back. Just like any other girl. I was originally a little afraid that she'd embarrass, me, but not anymore. She was cool.

We ran like this every week and it turned out to be a good thing and we were becoming friends.

Then one week she called and asked, "I have to meet someone after our run. A date. Because you are closer to the park, I was hoping I could bring some stuff and change at your place."

I was very conservative. And didn't want my neighbors seeing a transsexual visiting me in my apartment. But, I thought about it and realized that I didn't want to give in to the negativity about other people's lifestyles or be afraid of my stupid neighbors. I said, "Sure."

We finished the run and then she came up and said, "Nice place!"

"Thanks."

"Where's the bathroom and shower?" 

I took her to it and she took a long shower. Then the water went off and she asked, "Do you have a towel for me? I'm all wet." 

"Oh sorry, yeah, of course." And I went to find a clean towel for her.

She opened up the door and said, "Thanks."

She didn't just stick her hand out. She stood naked in front of me by the bathroom to take the towel. And she saw that I was a bit surprised and she started smiling.

"Max, you are such a prude." 

"No, I'm not."

"Then why did your face turn red as soon as I opened my door to get the towel?"

I was meanwhile trying my very best to look at her face and not look at her chest or down below. Although with my peripheral vision, I could already sense her penis. And I thought it might be rather large but I couldn't see for sure. She didn't seem to have implants or take hormones based upon her chest, but, it looked surprisingly feminine, although it was flat. Perhaps her smooth shiny hairless skin and slightly perky nipples were all it took to be feminine.

She meanwhile was enjoying the conversation. And enjoying how uncomfortable I was.

She said, "Max, I love that we are friends. Dating is horrible. I have to now get ready and put on make up and hide this..." She looked down. I took that opportunity to look down, too. It was very fat and very long. I did not know that penises could be that big.

She looked up and saw me checking her out and said, "It's so cool that I can hang out and not hide this from you. If we were dating, you wouldn't be allowed to see this for a long time."

"Why?" 

"Because I'm a girl, silly!"

"Oh."

"Yeah, I hate it. I wish it wasn't so big. I don't believe in hormones or surgery. But this is quite a challenge for me. If only it wasn't so damned big. Do you know that people have refused to have sex with me because of it? Guys and girls!"

"I'm sorry."

"It's okay."

I said, "It's a bit ironic, because a lot of guys would kill to be as hung as you."

"Yeah. I know. But what they don't know is that it reduces the amount of sex I can have when I'm in a relationship because people get sore. It definitely can attract some girls or guys. But it's unfortunately for kicks."

"Well, I think it's awesome. I'm sure someone lucky guy will be very satisfied."

She seemed happy about that and said, "You are so sweet." And went to give me a hug. I was a bit nervous. Her penis touched me and I was just wearing running shorts and a t-shirt so I had to maneuver around a bit. She pulled away.

Then she said, "But, I have to tell you, as a girl. I wish that my penis was just like yours. Then I'd be able to satisfy my lucky guy even more."

"How do you know what my penis looks like."

"I can tell. It's average. Just like I want."

I said, "I'm above average. But thanks."

She looked at my crotch carefully, "Really?"

I said, "There's a big different between what you've got and above average."

She said, gesturing to her penis and moving it a little bit, "Have you ever seen one as big?"

"No, as a matter of fact."

She smiled. I'll tell you what. If you want, because you seem a little bit impressed, just once, you can touch it. It'll be our little secret. I can see how curious you are."

"That's okay."

She smiled, "Don't be silly. Let's just get this out of our system. This will be good for our friendship. You'll never have to wonder and you'll be able to treat me like normal again."

"You're so funny, Joline."

She smiled, "Come on. After my date. I might be taken and then the chance will be gone forever. I'll be married with my white picket fence and you'll never get another chance." She was smiling at me, obviously having fun with how nervous I was. "Come." And she took my hand. I pulled back a little. But she held on and looked at me like I was an obstinate kid, and I relented.

She put my hand on her penis and I felt it and gave it a little squeeze. It got a little bigger. She was looking at me the whole time. She smiled mischievously when I held it. She then pulled my hand away, and said, "Okay, only for you Max." And continued to smile. It was starting to move and was getting even bigger.

She looked at me and said, "You are so nervous. It's so cute. I have to get ready though. But first let me give you a hug."

Then naked, she grabbed me and hugged me. Then she squeezed me again. "You are so nervous. I love it." 

She was getting fairly hard. I could feel her penis through my running shorts all the way up my stomach. I realized this and pulled my midsection away. "Oops, I'm sorry. I guess I should've foreseen that from the feel." She smiled some more, still holding on to me. She was fun. 

Now her monster was hard and I looked down and it was looking up at me. She smiled. I have to get ready for my date. 

"We're good, right?" She asked.

"Sure." 

"Oh wait one second. I just realized. We aren't done." 

"Oh?"

"Yeah. You got to see and feel mine. But, I'm left here and will never get to see yours."

I said, "Okay and quickly flashed her."

She nodded her head and said, "Max" you know that wasn't fair. But, I'm late. I have to go. We'll have to talk about this later. She smiled.

Then she took her towel and went back to the bathroom and got ready.

Shemale Becomes Friend Ch. 02



She left to go on her date. I hung out at home, watched TV, and ate dinner. The whole exchange was pretty exciting and fun and I was glad that she convinced me to actually touch her member, it was indeed a once in a lifetime experience. I wondered if perhaps my conservative nature was making me miss out on a lot of fun in life. But, I knew that I can't change who I am and so I couldn't really give Joline what she really wanted, except as a friend.

Later that night she called me up, "Max, can I come over to get my stuff." She didn't sound very good. She came over 30 minutes later. She was very upset. She went straight to my couch and started to vent, "The jerk just asked for head in his car after dinner and I said no and then he stopped his car to let me out on the side of a freeway. I had to walk back in these shoes which are ruined. Max, I wish more guys were like you." She put her hand above my knee when she said that.

"It'll work out, just give it time." I patted her shoulder. "Let's just watch some TV."

"Thank you, Max."

We watched a comedy on TV. We sat pretty close. She leaned her head on to me and acted very much like a little feminine girl. I marveled at how this feminine beautiful woman, nestled in my shoulder, so contently, could possess the equipment that she possessed. If there's a god, then I'd be curious to understand his plans. She calmed down. Before long she seemed quite happy and was laughing at every silly sitcom gag. She put her hand on my stomach and squeezed me when something exciting happened.

When the show was over, she said, "Thanks for being so wonderful, Max. I'm feeling so much better now. I owe you. I'm going to give you a massage to make it up. Lie down on the couch."

I said, "Okay," and lay on the couch. She looked at me and didn't touch me and said with a smile, "Max, you have to take off your clothes for a massage. You know that."

I looked at her suspiciously but she kept on smiling. 

"What's the big deal," she said, "I've already seen everything and besides, I believe you still owe me from earlier today."

I figured what the heck and I took off my shirt. She made sure to help me. I took off my pants as well but left on my underwear. She seemed satisfied with that.

She then touched my back. Her hands were cool. The massage really felt good. She traced her fingers along my skin. This clearly wasn't a professional massage. It was too light. But it felt really good and that was fine. Harmless fun. Then she got lower and got to my legs. She worked them very hard. Too hard, maybe this was professional, and I finally said, "Ow."

"Oops, sorry, tell me if it's too hard."

Then she went extremely light just tickling me really and it felt very good. But, it wasn't a massage it was foreplay. And I was getting chills and hard. She worked her way up my thighs and it got even more exciting. Then she reached my butt. First she massaged me on my butt. "I knew you'd have a good butt." She then put her hands under the legs of my underwear and traced her nails along the skin of my behind.

"Oooooohhhh," that was too intense. I'd never felt that before. She stopped for a second and asked, "Is that okay?"

I answered, "That was really intense." 

She said, "Okay, I'll do it lighter."

She then traced her fingers lightly on my butt again. And I squirmed. "You are tickling me."

"Sorry."

Then she went to my back and all around my body. It felt really nice. She then lay down on top of me and whispered in my ear, "How are you feeling?"

I said, "Great."

She responded, "Good. We should give each other massages after runs if you feel like this loosens you up."

She continued her massage. Then she got to the waist band and pulled it down past my feet and threw it to the side. I didn't do anything and just let her. I was now completely naked and she was on top of me giving me this massage which was really more of a titillation. But, it felt incredible.

Then she started again at my feet and massaged each of them thoroughly.

"I bet your feet needed that." She said.

She pulled my legs apart a little bit. She then worked her way up my calves. Gentle rubbing and then light titillation. This went all the way up my upper thighs. I was so hard.

She then reached my butt and grabbed one cheek which each of her hands and squeezed them. Her hands felt quite big and I felt quite small. She even separated my cheeks a bit. I guess to see me inside. I asked, "Everything look okay over there?"

"Looks wonderful."

She then let my cheeks go and rubbed my butt again. She used her nails again, and it was very intense, but she stopped as soon as I groaned and writhed. She then lightly rubbed around and worked her way up my back. She lay on top of me again, but this time I felt her bulge. She was hard. It felt heavy and solid. I don't understand how she hid it in that little dress.

She continued to massage me as she lay on top of me and whispered, "Was that okay?"

"Yes."

"I know we are just friends, but you are so cute, and unfortunately, I have some parts that get in the way sometimes." She wiggled her penis on top of me as if there was a chance that I didn't notice it. "I wish they didn't. So sorry about this." 

"I can't even feel what you are talking about." I lied.

"Really?" She pushed her hips towards me to make certain I knew what she was talking about. The novelty of having that monster pressed against me, between my butt cheeks, and the base of my penis, while I was naked, under a beautiful woman, expressed itself in my penis and throat. "

I didn't say anything for a few seconds as my heart fluttered.

I said, "It's okay. Everyone's different."

Satisfied, she said, "Okay, now turn around. I'll do your front." 

I was naked and hard. But, I figured why not. And I turned around.

She looked at my penis and was so excited, "It's so beautiful!!!! I love it!" 

"Thanks."

She approached it and massaged my lower stomach and thighs. "Have you ever had a penis and ball massage? It's very good for you."

"Never even heard of the concept."

She then touched my penis and massaged it. She cradled my balls with her other hand. She rubbed it very gently and massaged the whole area. I was very excited and she was too. She said, "that's your massage. But, before it ends can I just do one little thing?" 

"Sure."

She then lowered her head and licked my penis once, very slowly, from the base all the way to the tip. And then she kissed the tip once and I groaned lightly and she pulled away and smiled at me. I was so close.

"Thanks for being so wonderful!" She said. And then she kissed me once ever so gently on my stomach near my navel which gave me chills and made my penis jump. 

The lick felt great, the kiss felt even better. Why'd she stop? But, I guess I was pushing my luck to expect anything from a girl who is my running partner and who I was too conservative and backwards to date. Take what you get and be satisfied, I figured.

Also I was just too horny and I don't think I'd feel comfortable where I knew this would go if she decided that it would go there. She could've given me a full blow job and until I got off I knew I would not say no to anything. I know I would've felt weird about it afterwards.

She picked up my clothes and threw them at me. Then she said, "Thanks for taking care of me. I have to go now. It's getting late."

As soon as she left, I went to my bed and finished off the job. It felt incredible. What an evening for me.



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.



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."



Shemale Becomes Friend Ch. 05



I opened the door and Joline came right in smiling and I gave her a big hug.

This time, I would give her what she wanted and I would take what I needed.

I closed the door and took her by her delicate hand straight to the bed. She followed me, still wearing her jacket and still holding the bag and I pushed her down and kissed her and pulled off her clothing.

She giggled excitedly by my forceful passion.

She was naked. I kissed her breasts and nibbled my way down her body. I was hard and ready. No time for foreplay today, I thought. I stopped to find my condom in the drawer by the dresser. She was gleaming with joy. 

And then she giggled as I put on the condom, "You can't just have sex with me. You have to get the girl wet first."

I looked confused at her for as second as she smiled mischievously at me.

"I'll show you how." She leaned off the bed and grabbed her little bag and pulled out her tube of lube. She squeezed it and put it on her finger and then doused it over my throbbing penis. She then put some inside herself. "All wet," She smiled.

Wasting no time I pushed her back on her back on the bed and continued kissed her neck as my penis searched for her hole for a bit. Her legs were around me. He penis flopped between us hard. She guided my penis with her hand to her entrance, and as it touched her she moaned, "Ohhhhhhh."

Having my head insider her, I began to slowly probe in and out. It was tight. I was aroused. This would work. No problem. She made noises every time I went in, in time with me as I entered. She touched me with her hands. I was on fire. I felt like I barely started and I was already ready to cum. Every time I looked down, there she was smiling at me.

I was about to cum having only just begun. I stopped. She asked, "Why are you stopping?"

I said, "I'm about to cum."

She cooed, "Ohhh," that's so hot. And she touched me all over and my back and thrust up to me.

That was it. My orgasm began. I thrust into her as she moaned and touched me. I stopped still inside her. She kept touching me and kissing me as I lay on top of her.

Finally, I got up and went to the bathroom and threw out the condom and cleaned up. Then I returned to her in bed. She was under the covers on her back and I could clearly see the lump of her privates.

She opened up the covers and I saw her penis swaying towards me as she invited me in. I joined her and she held me as I rested. I felt her rod roaming around my backs and legs as we adjusted.

She teased me with hands too. 

I realized that she did not yet get off. "I'm sorry, I came so soon. I wish you didn't move when I told you that I was almost there."

She said, "No, I loved it. And besides, one of our advantages is that we have two penises not just one." And then she pushed her penis at me from behind.

I knew where this was going. She started kissing the back of my neck and her hand ran from my chest down to my thighs and crawled back up again.

She crawled her way on top of me and started to kiss me all over my body. "I'm ready," I said.

She pulled on a condom. She applied some lube to my hole with her fingers. She tickled me there. My legs were spread. I looked up. Wondering what I'd gotten myself into again. Wondering if this time would hurt even more or less. Wondering if I'd orgasm three times in one day.

My wondering stopped as soon as I felt her tip press against my hole. Slowly she prodded against my hole. Slowly going in. I was still a little tender but this didn't hurt at all.

She continued prod. It felt like she'd never get in. She entered at the speed of the minute hand of a clock. I was feeling teased. I grabbed her by her hips and she pulled me down and pulled my hands away. "This time can we do it my way?"

"Okay," I said, not knowing what this would entail. 

"Good," she said, "now holding my arms down above my head as she pumped in and out of very gently."

I relaxed. This felt good. I could relax for a while. And she kept on going. She slowed down and lay directly on top of me to conserve energy. She let go of my hands and I put my hands on her back.

"No, leave your hands where I put them. I have some very specific ideas about how I want to enjoy you this time."

I put my hands back. 

Then she continued her slow operation. Eventually I realized she was half way in. I'd barely felt any pain but I did feel a lot of fullness. And as she was in further, I felt her little undulations more fully. They felt very good. I just lay there and she undulated and entered me. I wanted more. I bucked my hips into her and she pulled back in tune.

"Can you just lay there passively for me. I want to do this slowly. I need to enjoy you gently without hurting you at all."

I stayed still as she undulated on top of me. I felt my insides being massaged lightly. I felt my penis hard between us. I felt deeply sensitized inside of me. These little undulations were intensely stimulating to me. I felt little orgasms from within.

She kept this up for an hour. I didn't know what to think. How long would she go. How slow would this be. Would she make love to me all night long? 

She was now completely inside of me and I could feel her so deeply. I had no idea how she could even fit but she did fit perfectly.

My tension couldn't get any higher and I felt my orgasmic tremors turning into contractions. She stopped and smiled at me and said, "Not so quick. Concentrate and relax. Let's make this last." I closed my eyes. This wasn't going to work. I was losing control. Her presence was just too stimulating.

"You know that I've never cooked you a proper meal?" She said, smiling trying to distract me.

I started to laugh and she laughed. That helped. But as soon as I stopped laughing that orgasm started to come back again and she felt my contraction.

She said, "It's okay. It'll feel good. Go with it. Just don't move."

Again and again I contracted. She meanwhile was moaning as I squeezed her inside of me with my orgasm. It was so intense that I could not move anyhow.

Then I finished my orgasm and looked up to her glowing. "Does it hurt?"

"No."

"Good." She continued to undulate on top of me. I felt good. It was now just a massage without the sexual tension slightly lower. She enjoyed herself. I lay there. Relaxed. She lifted one of my legs and pushed me to my side and spooned me with her member inside of me. Gently undulating the whole time. Another half hour passed. Every time I looked at the clock with curiosity I was shocked with how the time was flying. I'd never made love for so long.

She also played me with her hands. Those pointy fingers seemed to know the points in my body that would make me tingle. And she would do this in concert with her undulations. I resigned myself to being pleasurably manipulated all night long. I was not going to complain. I was just in shock because I never even imagined being made love to like this.

When would she orgasm? I wondered. 

Then around the 3.5 hour mark. I noticed that I was getting hard again. She noticed too. As she had been tickling me down there.

She had one hand over my whole penis and balls and another working my stomach and chest and nipples. Her mouth was on my neck. I felt like her undulations were getting a bit wider but by now I didn't even know what it felt like to not have her inside of me. This was my natural self.

Her bites became harder. Her massage because deeper and lighter.

She undulated a little bit harder. She moaned as she moved. Her fingers were manipulating me as well. I saw no need to hold back an orgasm this time as it sounded and felt like she was on the brink of one as well. I felt her squeeze her hands around me as she pulsated inside of me and moaned her deep moan into my neck.

She came and moved only a tiny bit and paused in between. But she was still hard. How did she do that?

This was now little more than cuddling, I was so used to her inside me, hard or not, that without her moving I could close my eyes and sleep. I felt like she was doing the same.

But, my dreams were the same. I dreamed that she pushed me onto my stomach and made love to me. I dreamed of her penetrating and pulling out and pushing in powerfully and intensely. I dreamed I was moaning for her and sighing as her stomach slapped against my back.

And then I realized this was real. She was still making love to me. In my dreams, on my back, on my side, and now my stomach. This would never end but I was loving it. I looked at the clock and I could see it was almost 6AM. My insides didn't hurt in a bad way at all. They only had intense pleasure. I started to contract. This orgasm was eeked out of me through her sheer intensity. She felt it and stopped and she pulled me to my side again. Her penis now softened. I didn't feel any pain. I fell asleep again.

In the afternoon when I did finally wake up, it was to the smell of her freshly cooked breakfast.

It was a finely crafted breakfast and a fitting start for a fun filled afternoon. I would take one moment at a time and I would just feel my way through.

The end.