Shemale Becomes Friend Ch. 05

Story Info
Joline calls the shots and manipulates her man all night.
1.7k words
4.64
54.1k
46

Part 5 of the 5 part series

Updated 10/31/2022
Created 11/27/2012
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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.

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AnonymousAnonymousalmost 3 years ago

Good story but seems unbalanced. She has pursued him from the beginning and as such is all about pleasuring him and taking it to the extreme. But she barely requires anything herself. He has lied to her about another girl, denied his desires even as he gave into them, turned cold and shitty after their first time, but then 180’ed immediately and invited her back to fuck her with almost no prep or care at all, came immediately and then was open to having his previously too tender and sore hole pummeled for hours straight. It was very hot but left me feeling unsettled that this won’t turn our healthy for either of them. Will there be more chapters to explore this?

GrrrreatImaginationGrrrreatImaginationover 9 years ago
Well, now.

I enjoyed this story (meaning all the chapters together). I liked getting to know them a bit, in a vague kind of way. I enjoyed his questioning and attraction to what was unfolding. Joline was a sweetheart, even if she was pushing the friendship.

The only thing that bugged me was in this chapter (05). It seemed to me that your story never had a climax (a literary climax). It just sort of faded out. Still a nice story of curiosity, but the larger story of their friendship, their romance, his attitude, etc., never really came into focus.

Anyway, thanks for this story, and please keep writing.

AnonymousAnonymousabout 10 years ago
there has to be more

there has to be more to this since he is just know starting to enjoy his girlfriend and all that she has to offer. Please write another chapter or two.

Omega ManOmega Manalmost 11 years ago
The End? :-(

This can't be the end to this tender and erotic love story.

AnonymousAnonymousalmost 11 years ago
great story!

I don't want to criticize, this was a great story, and I liked reading the previous ones, they had mystery, story, and exciting. My only complaint is that there was no description of her breasts. No mention of the size, and the feeling the dude must have felt when the did it. Anyhow, best story ive read here in a while, keep it up, and don't forget the tits!

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