Shemale in a Bar Pt. 02

"I see you are enjoying this babe. Please don't stop." I begged her.

"I love to watch you make faces while I give you pleasure." she replied

She was fucking my ass for another 10 minutes then suddenly stopped and pulled out the dildo. She then took two small size dildos, one black and one blue, and slid one right in my ass. While holding one steadily in she put the other one's head on beside it. Then she started pushing it in. It was a weird feeling. Having something in my ass already and another thing trying to get in. It was not painful or not likable but it was weird. She managed to push the head of the other dildo in too. Together that was about 6-6.5 inches in width. She moved it further in so they were in similar depth. She then held them with one hand and started moving. She went in and out, in and out again never taking them fully out. From time to time she took them in separate hands and twisted them in different directions or making exchanging thrusts-one in one out and repeating. After a few minutes of it, I started to enjoy it.

I enjoyed it so much I was again moaning and precum was dripping from my cock. Michelle took my dick in her hand and licked the precum off it.

She stopped fucking me with dildos and slowly took them out. She opened the box again and took out a clear-through middle-sized anal plug. She spread some lube in and slid it in my ass. I felt full before but this was a totally different feeling because it was not going in and out but just sitting, lodged in there. Every move I made it stimulated my prostate more and it sent shivers through my whole body.

She stood up and came to where my head was and asked, "You wanna help me get ready?" and swayed her hips a bit.

Her cock was dangling down, soft and from time to time she made it twitch a bit.

"Anytime you want dear." I replied and opened my mouth.

She moved closer and put her cocks head in my mouth. I licked it, sucked at it, making moans and sending vibrations through and she was enjoying it. Her cock was getting harder and longer now. I was enjoying giving her pleasure by sucking her cock. It almost felt like an addiction. I was feeling like a hungry cock slut and I loved it. I was so lost in my thoughts I was surprised when her cock pushed in my throat still growing. I almost gagged but quickly adapted and swallowed her cock.

About 5 minutes later she pulled out with a satisfied grunt and said, "Now we are ready for the main course."

Her cock was standing at full mast right in front of my face and I again felt a knot in my stomach about doing this.

She went around the bed to where she was before, spread my legs a bit more, and started applying lube on her throbbing cock.

"You sure you don't want to use a condom?" I asked.

"I can show you my receipt for a health check if you want. But I never had sex outside my shemale friends before so you are actually the first unknown guy in my bed. And as far as you told me about you, health is of most importance to you too." she replied then added, "And it will feel a lot more intense doing it without a rubber."

I don't know what I was thinking about that time. Probably nothing so I just blurted, "I trust you and I think you know it by now."

She gave me a warm smile and continued applying lube on her cock and then on my ass. She took out the butt plug and fucked me with her fingers a few times then removed them.

"I think we are ready." she said, gave me a wink, and positioned her huge dick at my hole.

She slowly pushed forward, my ass opened a bit and she managed to get about half of the head in. Then she met resistance and couldn't proceed.

"Hun, try flexing your muscles like when you go poop. Don't squeeze in but push out. It may sound weird but you will see it will help." she assured me.

"I will try." Was everything I said.

I pushed a bit and squeezed almost immediately. She patiently waited and I pushed my muscles a few more times. She then suddenly started pushing in slowly while I was still flexing my muscles.

"Just keep doing that." she reassured me.

Slowly she was penetrating me and my ass was stretching its limits to the brink of pain. I pushed through smaller pain and kept going. She was still pushing in. I felt a sudden lack of continuous stretching when my ass relaxed just a bit. I stopped and looked down.

She said with a smile, "The head is in darling."

"What? Only the head? Damn that feels like a whole arm is in there." I replied surprised.

"Oh we will make it there, after few runs if you will be up for it?" she asked with a wink.

"Hmm never thought about fisting before, but after seeing your monster cock it might be doable." I teased back.

She used this teasing and smiling and pushed in a bit more. Painfully I remembered there is something huge in my ass and I should make an effort to make it easier not harder.

After a few deep breaths, I said, "You can start moving now, I think, but slowly please."

She pulled out a bit then pushed in again, very slow and gentle as she could be in a situation like this. After 2 or 3 thrusts she pulled out slowly. I felt my ass gape then shrunk painfully. She took some more lube and spread it on my asshole and her cock again. She positioned herself again and started pushing in. I remembered what she said and started pushing my muscles and it really helped. I could feel her cock pushing in, stretching me in a good way.

Her head penetrated me again and I smiled.

She returned a warm smile and pulled out but not fully out. She stopped ¾ of the way then pushed back in. I was getting used to it a bit-I thought. She took it out again and instantly started pushing back in. It went easier this time and I was not feeling so much pain anymore. Probably because I was pushing my anal muscles all the time. She pushed another inch in and stopped when she saw me twitch. She waited for half a minute then pushed in another half an inch. I was feeling so full at the time it was like I was going to burst. Like when you really really need to go on the toilet.

She stopped again and pulled back to the head then pushed back in and again and again.

I was lost in a world of mixed pleasure and pain. My dick was semi-hard, excited but still in pain so he wasn't sure either. I was looking in her eyes, losing myself in those green meadows, moaning and flexing my muscles.

After a while of short thrust, she smiled at me and said, "Well hun you are doing good, already halfway in and you barely stopped because of the pain. You are a natural or you did this before." She was trying to relax me a bit.

"Damn babe that feels sooooo good. But I am not sure if I can take any more of it today. I think I am stretched to my limits for now." I replied in a mix of moans and grunts because she was still thrusting.

"No worries hun, we have time for you to take all of me and I doesn't need to happen today. You surprised me with this already and I am more than happy about it." she replied, bent over, and gave me a kiss.

While we were kissing and our tongues entwining she kept on thrusting and fucking my ass with only half her length. I was feeling nauseous at the excess of all sensations and feelings and I was lost in my own world. Thinking about getting fucked and I was enjoying it a bit too much.

She woke me up from daydreaming when she said, "I see you are starting to enjoy this a lot hun." and smiled.

I looked down and saw my cock was rock hard now and dripping precum.

"Did you ever tasted your own cum?" she asked.

"No, never" was my answer.

She bent over more and took my cock in her mouth, while still moving with her big cock in my ass.

After all the teasing, fucking, prostate rubbing I was barely holding back my orgasm. She took only my cocks head in her mouth but she put her hand on my shaft and started jerking. Only a few thrusts later I came. It was not as good as on the terrace during the night but it was still one of the best orgasms I ever had, even though my ass was hurting a lot now. She stopped moving with her cock and hand and just waited for my cock to settle down. She then slowly took me out of her mouth and closed her lips tight. She slowly pulled out my ass and she exited with a POP sound. I could feel my ass gaping and I thought about all that porn I watched when women or sissies gaped their asses. I was just like them now. It was an exhilarating feeling.

Michelle moved around the bed again and stopped, she leaned her head a bit up and tried to say something.

"Op.n yo.. m..th." was what I thought she said.

I opened my mouth and Michell leaned closer until she was about 1 inch away from my face. She then opened her mouth just a bit so she could control where it was dripping. My own cum hit me directly on my throat and started moving toward the throat. She then opened her mouth a bit more and the rest of my cum followed. When the last drops were gone she bent over and gave me a sloppy kiss. Our tongues were sliding around each other, enjoying and cleaning the other one.

She pulled away and said with a smile, "Now of to shower to clean us up."

"You didn't finish dear, let me do it," I replied.

"No need to, I am perfectly fine. After all, this was all about you and not me." She said warmly and caressed my cheek with her hand.

"If you are really fine with it, I suppose I can accept that." And gave her another kiss than a playful slap on her ass.

She smiled and pulled me over to the bathroom and under the shower.

We were hugging under the flow of warm water and it was one of the best moments in my life. I feared I might be falling for this girl and was not sure how it will end after I will need to leave the country.

I was washing her back when suddenly a naughty thought passed my mind. I pulled her closer and started massaging her perfect boobs. Her nipples got rock hard in a split second.

"Mmmm, what are you doing? Didn't we say we are done for now?" she asked.

I replied in a naughty voice, "You said we are done, but I am not done with you. I still need my breakfast."

I guided one of my hands down her flat stomach between her legs. She was already or still hard from before.

"Let's clean this thoroughly, shall we? We can't have you going around the town all dirty and pent up" I teased.

"Oh yes, that really wouldn't be appropriate." she replied and moaned.

I grabbed her cock and started jerking her off from behind. She was enjoying it as she leaned back on me. I moved a bit back so I was at the wall so there wasn't any fear for us to fall. I started with slow motions on her cock, while my other hand was pulling and squeezing her hard nipple. I was also kissing her neck and shoulders. Her breathing was deep and she was nearly lying on me. I switched to a faster pace on her cock and I also tightened my grip on it.

She was moaning more and more now.

I pushed her gently away from me and turned her around. I went on my knees and put both of my hands on her cock and started jerking it. I was mixing the choice of grip a lot. Hands behind each other, one on each side of her shaft, one going up and one down, turning my wrists and palms while moving up and down...

"I am close babe." She whispered and moaned.

I could barely hear her but felt her cock throbbing so I quickly positioned my mouth at the tip of her cock and slid my tongue just under the head. After about ten more tugs her cock exploded and her hot, tasty, sticky cum showered my mouth and face. Her orgasm was so intense her knees buckled and I barely caught her by her ass and pulled her toward the front so she fell on me instead of falling back.

"Are you ok Michelle? I asked worriedly.

She only nodded and said, "Just hold me for a bit."

We sat under the hot shower, me on the floor and her sitting on me while hugging and just feeling each other closeness.

After a few minutes, she came to her senses and gave me a kiss.

"I never had an orgasm like that just by someone jerking me. Who are you and how do you do that?" she asked in a kind voice.

"I guess we are just made for each other love." I replied and cupped her head in my hands.

"So what is next?" she asked in an interested manner.

"First I need to get back to the hotel and do some stuff, need to check a few things with my business and other stuff, reserve a dinner, and so on." I replied.

She seemed a bit down by that answer and said, "Ok I am glad we spent some time together. I really enjoyed it." Then added something in a voice so low I couldn't make out what she said.

"You know a good place for dinner around here? I need to invite an important person to dinner so we see if we can continue our cooperation." I teased

She was so lost in her world she disappointedly replied, "I know of some good and excellent places, but I wouldn't take your "business partner" there."

"Would you make a reservation for two in my name at the place you like the most at let's say 7 pm?" I replied in a calm voice.

"I won't be your dating organizer." she said now in a low angry tone.

"Hmm really? You won't? Well, I guess I was mistaken to think you would like to go to dinner with me today. Then it is best if I leave." in the end I couldn't contain my laughter anymore and I just started smiling out loud.

"Oh, you bastard." She punched my shoulder and laughed out loud with me, then added, "For a minute there I really thought this was it between us and I was only a one night stand for you."

I leaned closer and kissed her.

"I really need to leave and check a few things back in my hotel. But I would love to continue this between us. So will you come out on a dinner with me?" I asked.

"Of course I will you meanie. I like you a lot and this was one of the best days of my life. So yes I would love to go out with you anytime you want." She replied with a wide smile on her face.

"Than I will see you for dinner. I will come to pick you up at 18.30 if that is ok with you?" I enquired.

"That would be perfect." She said.

After that we got out of the shower and get dressed, she walked me to the elevator. When the door opened she hugged me tight and gave me a long and passionate kiss.

I could barely make myself walk away from her, but I had to or we would never leave this place and would be humping like rabbits.

Story will continue in Shemale in a bar Pt.03