Shemale in a Bar Pt. 02

This is a continuation of my story: Shemale in a bar Pt.01

*****

My dick twitched

We walked hugging each other toward the corner of the street. There we waited for a taxi to drive by so we could get a ride to her place. We called out for a passing taxi and he stopped so we could get in. Michelle gave him the address and we were off. We were sitting in the back seats, chatting and hugging. From time to time my or her hands wandered a bit over the other’s body. All in all nothing special/naughty happened during the drive.

Taxi stopped so we exited and even though she wanted to pay, I insisted on paying and replied, “It’s the least I can do after what happened at the club dear.”

She smiled and kissed me. “That was nothing naughty boy, just you wait and see.” she replied.

It was hard but I pulled away from her and looked around a bit. It was a nice neighborhood. Later I found out it is somewhere in the middle between best and average places. It was an apartment building with multiple higher-end units. We entered the building and took the elevator to her floor. She used a card so I expect each card opens only 1 floor. There was only 1 door on a short hallway out of the elevator so I thought her apartment mus be quite big. I was expecting it but was still positively surprised when she opened the doors and invited me in. She gave me a tour of the place. It was not lavish but it was a high standard for most people living in the world. 1 master bedroom with bathroom and wardrobe room, 2 smaller bedrooms, 1 smaller room, cabinet, 1 bathroom, big kitchen with dining room, very big living room and what I liked the most: large terrace with a whirlpool and stunning view over the city.

I was so lost in the view I failed to notice her come closer. I felt her hands reach around my waist and she hugged me from behind. She cuddled closer and kissed me on my back.

With a grin on my face I teased her, “Is that a gun under your dress or are you just happy to see me?”

There is was that contagious and warm smile with a chuckle from her. “Well it seems I am enjoying my view far more than you dear,” she said with a wide smile.

I turned around in her arms and pulled her closer, lifted her a bit, and replied, “Hmmm well there is an amazing view where I am looking now.”

We kissed.

Hugging, rubbing on each other, hands wandering, exploring… My hands sliding down her back, continuing all over her ass. Followed by a smack on both of her ass cheeks simultaneously. A moan escaped her mouth. I caressed her butt a bit more than I grabbed below the but and lifted her. Her legs automatically went around my waist and locked behind my back.

She playfully smiled and said, “What are you doing mister?”

“Just taking what I want and desire.” I replied with a sly smile.

We continued kissing. We were totally lost in the moment, oblivious to anything around us. The top of my hard cock was grinding on her perineum. while her cock was rubbing my front side from my stomach up to my nipples.

I wondered what it would feel like to lick her cocks head in this position.

My dick twitched at that thought.

I was getting hornier by the minute. Grinding on each other was making me lose my mind.

She was doing no better, sucking on my tongue, biting my lips, forcing her tongue in my mouth. One of her hands on the back of my head and the other one playing with my nipples. Her breathing was heavy with lust and she was grinding her throbbing cock against me in a horny and aggressive manner.

I could almost “taste” the lust and horniness in the air. Well, I wasn’t faring any better. Squeezing her ass with my hands, spreading them, and squeezing. I pulled one of my hands up and after a few tries opened the clamp on her bra.

She moaned with anticipation.

With the same hand, I traveled around to the front of her body and managed to pull her bra up from her breasts.

She was still kissing me while I felt her wiggle and pull her bra away and threw it back over her shoulder.

My hand brushed on the side of her boobs, caressing her through the dress. I felt her nipples harden even more. They were pushing through the dress. While still caressing her side I slipped my thumb over her hard nipple. She shuddered and moaned. I grabbed her nipple between my thumb and index finger and gently squeezed and pulled. I made circles on her nipple with my finger, flicking it from time to time. I switched hands and did the same on the other nipple.

She moaned and threw her head back. I took that opportunity and licked the other nipple with my tongue. She almost jumped out of my hands at that move. I moved my hand from her boob to her back and held her tight, while I used my tongue on her nipples. Licking, biting, sucking on them. Even through dress, I could feel them so hard she could probably cut diamonds with them.

She was turned on so much she was rubbing her cock harder and harder against my body. I continued playing with her nipple while my hand on her ass slipped a bit to the middle and found her way between her ass cheeks. I caressed the space between the ass cheeks by rubbing my hand up and down as far as I reached.

“What are you doing to me?” she asked. “I’m going crazy here,” she added in a low voice full of lust.

“Hmmm, I think you are not at your limit babe.” I teased and added, “Yet.”

In the meanwhile, I was still sliding my hand up and down between her cheeks.

“But I know what will get you there.” I said with a wicked grin and slid a finger up her butthole.

She shuddered and intensified her grinding against me. She changed the way of her grinding so she could use my finger up her ass to her benefit.

I thought there is nothing I can do to surprise this girl. She just enjoys everything I do to her.

She was grinding against me so hard that her dress was pulling up, so soon my shirt was the only thing between my body and her hard, pulsating cock. She was fucking my finger like she was impaling on a hard cock. Those moves made her cock grind closer and closer to my face.

An idea crossed my mind and I lifted her a bit more. She was looking at me with a mix of lust and confusion.

Probably asking herself what will happen now?

Soon her dick was in reach of my tongue. I stuck out my tongue and licked the tip of her hard cock. It twitched. I was gently running my tongue around the head of her cock and licking glans. Her legs slid down, she couldn’t have them around me anymore because she was too high and my hands were in the way.

She moaned, threw her head back, and put her hands on the back of my head.

“Mmmm, yes babe.” was all she said.

She was pushing on the back of my head more and more, wanting for me to take her in my mouth.

But that was not my plan. When she was lost in the pleasure, moaning and sighing, I took my left hand and slid it around her belly to the left side of her ribs just below her breast.

What happened next surprised her.

With my left hand, I pushed on her side and pushed her to her right, and with my right hand pulled her ass to her left. She noticed she was “falling” over her side and panicked.

“Watch out.” she yelled.

She went stiff and tried to grab my shoulders to steady herself. By that time it was already too late. In a swift motion, I pushed her over the tipping point and when she turned, my left hand slid to her back and locked with my right hand.

She started saying something like, “What the.” By then we ended up in a standing 69 position. With her cock right in front of me I took her in my mouth.

She gasped, “Ooooh, I didn’t expect this. You had me worried there for a moment.”

I grinned and mumbled something,.

That sent vibrations through her cock and she moaned again.

At the time my focus was on her hard, throbbing cock in my mouth. I could feel it pulsating taking it down my throat. I pulled a bit back and licked the precum with my tongue. It still tasted sweet. I was so lost in my thoughts I didn’t even notice she unbuckled my belt and dropped my pants and boxers to the floor.

I gasped and moaned when she took my dick in her mouth.

“Mmmmmm.” was everything I could say with her big dick in my mouth.

After a while, she pulled away and asked, “Can we lie down. I am starting to feel weird in this position.”

I replied, “Of course dear.” With a chuckle I added, “We don’t want all the blood in the wrong head now right?” and pinched her butt.

She laughed out loud. There it was that warm smile that sent shivers down my spine.

I turned her around and dropped her to her feet then went and lie down on the ground.

“Would you like to sit on my face dear?” I asked with a smile.

“And here I was thinking you only want my cock.” she replied with a naughty tone.

She stepped over my head and swayed with her hips a bit.

“That is a sight to die for.” I said

She kneeled down and gave me a wet kiss saying, “You are such a sweetheart.”

She then moved her hips over my head and her ass was in front of my mouth now. I stuck out my tongue and brushed it against her hole.

She shivered.

I ran my tongue around the hole a few times, then guided it a bit down and licked her perineum. I could still taste my saliva on her from the back alley encounter. Mixing with her sweat and remnants of cum it made me even hornier. I used my hands to spread her cheeks wider and focused on her butthole. Probing it with the tip of my tongue, slowly pushing, and forcing my way in. The hole stretched a bit to let my tongue in. When I had my tongue in as far as I could, I started tongue fucking her boy pussy.

She was moaning and grinding on my face clearly enjoying it. I slipped one of my hands from her ass to her throbbing cock and started to jerk it.

“Mmmm, yes babe. Lick my ass as deep as you can while you stroke my hard cock.” she said moaning.

After a while, I pushed her hips back from my face a bit so I had a full view of her balls and cock now. I slipped my tongue out and flicked her balls with it. Then I took one in my mouth while still jerking her hard cock. I circled my tongue around her balls, sucking, licking, and nibbling them. I started teabagging her. Taking one of the balls in my mouth, pushing it out, and repeat with the other. After a few turns, I put both of her balls in my mouth. I licked them while sucking and pulling them away as far as my position allowed. I released them with a loud popping sound.

When I pulled her balls out of my mouth I said, “Why don’t you put my mouth to better use and stick that big cock in my mouth.”

She nodded with a spark in her eyes, raised her hips a bit, centered her cock on my mouth, and slowly pushed down. Precum was dripping on my face and in my mouth while she positioned herself. Then my mouth and my mind were full of her dick like a few times before. Again she started slowly, pushing in until she met resistance, pulled back, and pushed in again deeper and deeper. It was an interesting feeling having a dick upside down my throat. Instead of looking at her gorgeous face and boobs, I looked at her balls and shapely ass. Soon she was fully buried in my throat and her balls were on my nose and eyes.

I chuckled and thought, “This must be funny to look at.”

I almost jumped up from surprise when she grabbed my cock.

“You didn’t think I forgot about you do you?” she said. “You can’t be the only one having fun around here.” she added with a grin and spit on my cock.

I couldn’t talk because her cock was still balls deep in my mouth. So I just moved my hips left, right, up, and down a bit.

“So you are eager to put your dick somewhere hot and wet?” she said and added, “But what if I don’t want to put a cock in my mouth. I don’t know where this prick was before. Probably in some whores mouth or ass.”

I couldn’t reply because at that point I was focused on sucking that beautiful, thick cock. The only thing in my mind was her pleasure and to taste that delicious cum again.

She leaned closer to my cock and I could feel her breath on it. She gave it a kiss.

“Oh right, it was in my mouth before. How silly of me,” she said jokingly.

With those words, she took me in her mouth and started sucking me. Her hand was holding, squeezing, and pulling on my balls. It was a mix of pleasure and pain and I was longing for more, my dick hard as a rock. With her other hand, she went down between my legs and rubbed and teased my asshole. No girl ever did that to me and I was enjoying it very much.

I had my hands on her ass and was pushing her down my throat with every thrust she made. Her balls were slapping my nose and eyes. I was using my tongue as much as I could but it was hard because there was not much space to do it. Between trying to get some air and the feeling of her balls on my face I was lost in the world of COCK again. Hard, throbbing, long dick in and out, in and out. Saliva running down my face to my eyes over the forehead to my hair and on the floor. Balls slapping my face making weird wet flopping sounds. When she stopped with her cock balls deep and wriggle a bit balls spread saliva all over my face, my eyes were burning and I didn’t see well by that time, Still, I was enjoying it a lot.

“I wonder why I am enjoying this so much?” was what I was asking myself. Until today I never sucked a real cock and now 5 blowjobs later I am acting like a hungry cock slut. No other thoughts than breathing, cock, balls, and cum. And I enjoyed it a lot. I was nearing my orgasm already.

Feeling my cock throbbing and twitching she stopped jerking me. I made a disappointed sigh and she chuckled.

“I have a surprise for you babe.” She said.

I couldn’t see what she was doing but I soon found out. She licked her finger and started circling my asshole, while still firmly holding my balls and cock with her other hand. When my cock stopped throbbing, she probed my hole a bit with her sticky finger. She pushed it in a bit and held it there.

“Relax babe, I am not going to hurt you,” she said in a soothing and friendly voice. She also pulled her ass up so I could breathe normally.

Only then I realized I was squeezing my muscles and was all rigid. I took a deep breath and relaxed a bit.

“I think I am ready,” I replied.

She licked her finger again and then took me in her mouth. I visibly relaxed at this and she used it to slid her finger in. One knuckle in and she stopped. She flipped her tongue around the head of my cock and waited few seconds before pushing that finger in a bit more.

“Two down, only one left hun.” she said and continued.

I soon felt her hand against my hole and her whole finger was in. She moved it in a circling motion a bit making some space and letting me get used to the feeling. She was still sucking, licking, and nibbled my cock. A few moments later she slid her finger out but left one knuckle in, then in again and again and again.

I was more relaxed at that point, so she turned her finger a bit and made a hook pose with it, and brushed my prostate with it.

Involuntarily a loud moan escaped my lips.

“Someone likes it, it seems.” she smiled. “Wait for the finish.” she added.

She started moving her finger in and out faster now and in the meantime, she continued sucking my cock.

I was in heaven. Never felt this before and it was too much for me.

Clearly, she knew I was at my limit so she removed her hand and mouth from my cock and continued stimulating my prostate. About 5 seconds later my cock erupted. It was nothing I ever felt before. It felt like I will piss but instead, I was cumming, and boy I was cumming hard. Sperm shot over her face, boobs, and around her. If she wasn’t positioned over me I would probably shot the cum all over my face too. With every thrust of her finger, another shot of cum came out of my cock. When it was over I was like a ragdoll. It was good I was on the floor because I couldn’t feel my legs and my mind was spinning. So intense was the orgasm and I was breathing deeply and just lying there.

When it was over she pulled her finger out of my ass and licked my cock and sucked it a bit. She didn’t clean her face though. She sat up and looked at me.

“I don’t know what to say,” I said in a hoarse voice.

She just smiled and waited for me to calm down.

“What the hell was that? Thank you, thank you. I have never felt anything like this. It was amazing” I whispered.

She replied, “This was nothing, wait until you cum with a cock up your ass. That is the best feeling.”

I came to my senses and remembered she didn’t cum yet.

“You didn’t finish yet. Let me help you finish then we can chat about future possibilities.” I said.

“You don’t need to do that dear, I am OK.” she replied and added, “I know how overwhelming the first time can be.”

“Nonsense, it is the least I could do after what you just did.” I replied. “And after all, I love your cock down my throat.” I said with a grin on my face.

She winked and moved closer. She was still hard so she was enjoying it too. She climbed on top of me again and pushed her cock in my mouth again. She didn’t lie down but was bent over me, supporting her on her hands on the sides of my waist. Again she started slow and increased the tempo of thrusts every few seconds. The air was filled with sounds of choking, balls slapping, and her moans. She was fucking my throat like behind the club before. I was loving it. I loved the taste of her cock in my mouth mixed with her precum. I stretched my hand a bit and positioned it so she rubbed her perineum and ass against it with every thrust she made. She took her dick out from time to time and slapped me across the face with it a few times.

“You like a big, fat cock you slut?” she teased.

“I love your cock, Michelle.” I replied.

“I wonder if you loved those 2 cocks behind the club a few hours ago too, slut.” she said in a playful tone.

“As long as it is attached to a beautiful shemale and you allow it, I will love it, Mistress.” I said.

“That is something to think about.” She added with a smile. “Now lick my ass.” she added.

I stuck out my tongue and licked her hole. I pushed my tongue in making circular motions, licked around the hole and in again, caressing her balls with my hand. She was jerking her cock in the meanwhile. I was loving the feeling of my tongue in her boy pussy. It smelled and tasted delicious.

I heard her breathing getting shallower and rapid.

“Open wide.” was all she said.

I opened my mouth and few strokes later her cock twitched and spurted the first load of cum. It hit me straight on my tongue and dripped down my throat. Her cock was shooting and shooting cum, load after load in my mouth and on my face. I swallowed and my mind was overflowing with the sensation of her cum again. Sticky, hot, tasty cum. I was loving it. Her cock was now just twitching and no cum was coming out anymore. I took her in my mouth and licked it. I focused on licking around the head and around the hole. Followed by sucking at the head, kissing it, and licking the shaft clean. When I wanted to clean my face she stopped me.

I was wondering what was she doing.

She bent over and kissed me. Our tongues twisting, probing each other’s mouth, I hugged her and pushed her head firmly to me. We were locked in a kiss now. Because her face was turned the other way than mine our tongues went deeper than before. Nothing was obstructing the way to explore a bit more. We were kissing for a long time then she pulled us apart a bit. I looked her in the eyes.

“I could get lost in those green eyes. They are like endless meadows.” I said in a loving voice.

I was so lost in thoughts I almost jumped when she licked my face.

“Oh, you are a kinky one.” I said and smiled.

I let her lick me then I grabbed her head, held her in place, and licked her face clean too. After we were “clean” we got up. My knees were still soft from the last orgasm but I still took her in my arms and kissed her. We just stood there, naked on the terrace, hugging and kissing.

When we stopped she said, “Let’s go to the whirlpool and relax a bit. I will just go and grab us something to drink. Is wine ok?”

I replied, “Of course dear. As long as you are beside me any drink is fine by me.”

She smiled and went toward the kitchen and I moved to the whirlpool and climbed in. The water was warm and it felt so good I almost drifted into sleep.

She came back a few minutes later with a bottle of white wine and 2 glasses. I took those so she could get in the whirlpool without any problems. I poured glasses half full and offered her one.

“To a gorgeous and lovely lady who made my first time very pleasant and memorable. And many first times at that.” I toasted and winked.

“You are too nice dear. All I did was enjoy my evening in a good company.” She replied with a smile and added, “Well we need to find new ways to keep you in my company so you won’t run away.”

“I wouldn’t even think of running away after today dear.” I said and blew her a kiss.

We were talking and chatting about different things. From our past, to what we do in our lives, future plans…

We were so engulfed that we blinked in surprise when it started dawning.

“Darn, it is morning already. I best get to the hotel and get some shut-eye.” I said in a haste.

Suddenly all the adrenaline of the night passed and I was tired as hell.

“Well you can go I suppose.” She said in a sad voice then shyly added, “Or you can stay here and we go to bed together.”

I didn’t even think about it and just blurted, “Who am I to turn down an offer to lie with a goddess.”

She chuckled and rose from the whirlpool. She extended her hand, I took it and she led me to the bedroom. We went to the bathroom and I let her wash first then I splashed my face a bit and cleaned myself. When I entered the bedroom she was already in bed, covered with a blanket. I took a minute to take in the sights and smiled to myself how lucky I was to come on this trip and meeting her in that bar yesterday. I moved behind her, spooned her, and kissed her on the neck.

I whispered, “Goodnight, dear.”

She squeezed my hand around her belly and replied, “Goodnight hun.”

It was hours later when I woke up. I was not sure where I was. I looked around the room a bit and it came to me where I was and what happened last night. Even though my jaw hurt a bit it was still the best night ever. I looked to my right and saw her. Lying there, sleeping peacefully, her magnificent boobs on display. I was in love. She was gorgeous and she really made me feel good and special.

I was thinking about what to do to make us even, “Breakfast in bed? No, that’s to cliché. Stick my dick in her mouth while she is sleeping? No, that’s forced intercourse. Hmm, what to do? What to do?” An idea crossed my mind but it needed some preparations. “Will I really do this?” was what I was asking myself.

I got out of bed as quietly as possible and went to the bathroom. On my way, I grabbed my phone from the nightstand. When in the bathroom I sat on the toilet and opened up an internet search on my phone.

Searching for: “How to properly do an enema. Which position is best for first time anal. How to prepare your ass for anal intercourse.”

I didn’t want to rummage through her stuff so I went to the shower and unscrewed the showerhead from the tube. I set the water to warm and opened it just a bit.

I was awkward at doing it. How to position myself? Can I do it in another easier way and so on. At last, I ended up on my back, legs thrown back over my head and the end of the tube at my asshole. I let water in. It filled me with warmth and I continued until I was feeling really full. I removed the tube and waited for another minute then stood up. I barely made it to the toilet. I sat there and waited while water was pouring out of me. When it stopped I went and repeated the process just to be sure I was adequately clean.

I checked the mirrored closet at the sink if there is some toothpaste so I can clean my teeth so I won’t be all smelly.

I found a tube of lube there. Not sure why it was there but I used a bit of it and tipped it on my index finger. I slid my hand behind my back and spread it around butthole. I made several circles then stuck my finger in. Surprisingly it slid in without resistance. I started moving it in and out for several minutes. After that, I tipped a bit more of the lube on another finger and I started pushing both of them in my ass. There was some resistance at first but I made it in after several tries. I removed them and inserted them again and again. I stuck them in and moved them in different directions, wiggling with them, then trying to spread them as much as I could. After a few more minutes, I stopped finger fucking my ass and cleaned them, put the lube where it was, and walked back to the bedroom.

I was as nervous as hell. “Am I really doing this?” I mumbled to myself. “You sure you want to do that? After it will be done, there is no way out of it anymore.”

I was standing at the feet of the bed looking at her. She was so peaceful and beautiful.

“How the hell did I end up with a girl like this? I am one lucky bastard.” I thought to myself.

I went to my knees and went under the sheets towards her. I saw her feet and moved them gently a bit further apart so I could get closer to her groin. I made it there without waking her. I looked at her flaccid cock.

“I wonder how it feels like to let it grow in your mouth?” I silently smiled and lied down between her legs. I put my nose near it and took a whiff. She was smelling nice and clean because we were in a whirlpool for a while before going to bed. I put out my tongue and licked it gently then stopped. Nothing happened, She was still sleeping. I licked it again, this time I used my tongue to lick it around the head, gently moving it a bit. It stirred a bit and I kissed it on the tip. I left my lips on the tip and slid out my tongue underneath her cock. I wiggled left and right a bit with the tongue then opened my mouth and took the head in my mouth.

Michelle shuffled a bit so I froze in my spot with her cock still in my mouth. She stopped moving and was still sleeping.

I felt like a pervert trying something naughty. Or a freaking agent stealing state secrets (in this case her cum) from the enemy. I chuckled and sent vibrations through her cock and it stirred again. I started gently sucking at it and using my tongue to stimulate it more and more. I licked the glans below the head and got the desired effect. It was growing in my mouth. I felt excited like a child getting a lollipop. Her cock was pushing outwards now, slowly growing in my mouth and I loved the feeling. It was growing and spreading, filling my mouth. I had to move a bit lower so it didn’t push in my throat. That would surely wake her up. I was still stimulating her cock with my tongue and I put one of my hands on her shaft so I held it in a certain pose.

She was half hard now and getting harder, longer, and thicker. She moaned from time to time.

“I hope she is dreaming something nice.” I thought to myself.

I had to change position upward a bit because her cock was fully hard now and I couldn’t hold it down without hurting her. Her cock was filling my mouth and it was getting hard not to just take it down my throat. I loved playing with her cock, I pulled my mouth away and licked it. Then engulfed the head again and licking the top. With one of my hands, I started caressing her balls and with the other, I went up to her big boobs and caressed one of them.

Suddenly there was light. I looked up. I saw Michelle pulled away the sheets and stared at me in wonder. She relaxed a bit when she saw who was between her legs.

In a sleepy voice, she asked, “What is going on?”

“I just thought this wake-up method would make your day babe.” I answered.

“I was hungry and couldn’t find anything tasty besides you and your thick cock.” I added with a smile.

She laughed out loud, “Oh my what will I do with you.” She was quiet for a few seconds then said, “Let me at least wash my teeth so I can give you a good morning kiss. Also, I need to pee so if you are not thirsty you better let me go.”

I smiled and answered, “I would love for you to pee on me one day. But I want something else today.”

She shook her head in disbelief, “You really are a kinky one aren’t you? Be careful or I might lock you up and keep you for myself.” she added with a smile.

“Don’t make promises you can’t keep.” I replied.

She stood up, still shaking her head and smiling. She went into the bathroom and I waited for her in bed. She came back in less than 5 min and lie down.

“So you decided to get some dick instead of breakfast today? she asked and flopped with her cock a bit.

“Oh my breakfast is coming, I just need to milk it out first.” I said jokingly.

I grabbed her cock by the shaft and held it in an upward position. I went down with my head and licked her butthole first. Just enough to tease her a bit and get a few moans from her. Then I went up and licked her balls. I took them in my mouth and sucked them, nibbled them, and caress them with my hand at the same time.

She was lying down and looking up toward the ceiling. Her eyes were closed and she let out a moan here and there. No instructions were coming out her mouth for me to follow or how to do it better. So I thought she likes it.

I started licking her hard cock. I started at the base from her balls and up to the tip then back down, I flipped my tongue to the side and licked it all over again. Same on the other side. I put my lips on the side of her shaft and slid them up and down, teasing with my tongue in between. I gently nibbled it too and she moaned. I pulled back a bit and took a good look at her cock. This was the first time I really saw it. Sun was shining so I had a good look.

This thing was really big. Before I thought it was about 9.5inches but it was closer to 10.5. I had both of my hands on her cock and there was surely enough space for one and 1/3rd more. Even if I put it in my mouth it would still penetrate my throat before I could reach my hands.

It was also pretty thick. My hands didn’t fit all the way around so it must be around 8.5 inches around.

She is circumcised and her head was a thing of beauty. Mushroom-shaped with no skin around when pulled down. Edges on the cocks head were sticking out, throbbing, making it a delicious target to lick it, suck it, run my lips all over it, over the edge, back and again and again.

The skin was smooth and thin so her veins were seen below it. Her veins were pulsing and pushing out from below the skin and it was mesmerizing. This is why I felt it really stimulating while deepthroating it before. Veins giving the extra pleasure on entering and sliding through mouth and throat.

All in all, it was a perfect package. Big, thick, long, hard, throbbing, pulsating, mesmerizing monster of a cock.

Suddenly I felt a panic in my stomach. “How the hell will I take this up to my ass? Damn, I could have chosen a smaller one for the first time.” And I bragged before her yesterday saying, “Go big or go home babe.”

I pushed my thoughts to the side, said to myself, “Don’t be a pussy.” And continued sliding my lips up and down her shaft. I planted a few kisses along the way and she moaned.

After some teasing, I stopped at the tip of her cock, swirled my tongue around the head, licked its tip a bit then took her in my mouth. Half of the head at first, then whole. I created a vacuum-like position with my mouth and started sucking at it harder. Still, only the head was in my mouth. I released the air from my mouth and pushed my mouth lower on her cock. She entered my throat and it relaxed on the first try this time. I hoped I could do that with my ass too. I slowly proceeded down her cock until I hit the base and licked her balls with my tongue.

She purred like a kitten.

“I still can’t believe it how you can do it this good and deep even on first experience with a cock. I was stunned yesterday and I am still stunned today. Even some of my shemale friends couldn’t do this after 5 or more complete blowjob sessions.” She said in a low voice with a lot of moans in between.

“A guy must have his secrets.” I answered when I pulled my mouth free of her big cock.

“As long as you are this good, I don’t care for a few secrets.” She said playfully and gently brushed her hand on my cheek.

I continued by licking and sucking her cock. I was dripping more saliva on purpose just to make it wetter and hoped it will be enough for later. I took her out of my mouth and slapped my face with her cock a few times.

“God I love this throbbing cock.” I said and kissed it then asked, “Babe I want to try something if you are up for it?”

“Sure, what do you want to try?” she replied in an interested tone.

“I would like to feel you inside me, babe.” I said shyly.

“Of course dear, You felt it a few times already, what is one more time right? You want it rough or gentle?” she asked.

“You misunderstood me, love. I want it in my ass.” I said looking down feeling ashamed.

She stood up and came to me, lifted my head with her hands and gave me a soft kiss, and said, “I would love to be your first dear, but I am not sure we will be able to do it today.” She gave me a reassuring smile and led me to the bed.

“Lie down on your back hun.” she said and added, “I will be right back, I need to fetch few things.”

She came back in a few min with a middle-sized box. She came and sit beside me on the bed then opened the box. There were about 10-15 dildos and anal plugs in the box, sizing from small to large, mixed colors (red, pink, black, skin color, blue, grey…) some ropes, handcuffs, latex gloves, and a big jar of lube. She pulled out the jar of lube, few dildos from small to the medium size then covered the box and set it on the ground beside the bed.

“We need to start small or your ass won’t even let this small-sized dildo in without forcing. And I don’t want to hurt you, because I want you to enjoy as much as possible.” She said in a serious but warm tone then added, “You also should go and do an enema before we do anything.”

“I trust you fully dear because you know I have never done this before,” I said in a nervous chuckle. “Oh and by the way I already did the enema and some research before you woke up because I wanted to surprise you.” and I winked

“I like surprises like these and you really thought about everything beforehand.” she said then added, “Now let us start with something relaxing.”

She bent over me and kissed me. Her lips lingered a few moments on mine then she moved to the side of my face and kissed my ear. Then licked and nibbled the earlobe. She was lying on me so I felt her boobs pressing against me and her cock was squeezing mine. It was an interesting experience but very pleasurable. She started kissing my neck. She gave me a few sloppy kisses on it and then made a hickey. She continued downward toward my chest and with her mouth caressed one of my nipples while with one of her hands she teased my other nipple. They went hard soon and I shivered with pleasure. She moved her head down and caressed my body with her long hair.

I smiled and laughed, “That tickles you meanie.”

She just smiled and continued for a few more seconds then went lower again. Now she focused on the vicinity of my cock. She caressed my thighs with her hands and gave them a few kisses. She then caressed my stomach with her hands and was still kissing my thighs. She was moving closer and closer to my groin. She gave my semi-erect cock a gentle flick with a finger, smiled, and kissed it. She cupped my balls in her hand and started massaging them while still kissing my dick. She went up and down my cock with her tongue, sliding it up and down and around, making it all wet. She gave a few kisses on my balls then went back to pleasuring my shaft. She then took me in her mouth and slowly and gently started bobbing her head up and down. While she was sucking me she had a wicked smile on her face and I knew she was enjoying giving me pleasure.

She took my wet dick out her mouth, pushed on my thighs, and said, “Spread your legs a bit babe, I need to get in there.”

I obliged and spread them. She lowered her head below my balls and stuck out her tongue. She touched my hole and I groaned with pleasure. Rimming always turned me on and gave me pleasure beyond anything else I experienced until that day. She used the whole width of her tongue and was sliding it up and down my crack from balls to the point she reached and back again.

“Mmmm, that feels so good Michelle.” I said in a horny voice.

She continued and from time to time probed my ass with the tip of her tongue a bit. She went up to my balls again and started sucking on them. In the meanwhile, she opened the jar of lube with her hands and spread some on her fingers.

“This might be a bit cold.” she said and gently put her fingers on my hole. She then started moving them around the hole, sliding over it, and doing a damn good job at teasing me. She slid her finger all the way in on the first try and quickly removed it.

“Sorry I didn’t mean to be that rough.” she said apologetically.

“Heh, don’t worry hun. I practiced a bit in the bathroom after I did an enema. Probably that’s why there was almost no resistance.” I said playfully.

“Oh you horny slut.” she said in a cheerful voice.

She continued with her finger and slid it all the way in again then moved it around a bit. Because there was no problem she pulled it out and set two of her fingers at my hole. She started slowly and my ass gave way and spread to engulf her fingers in my warm hole.

“Oh, this is going better than I thought. Just remember how rigid you were on the terrace during the night.” she said.

I didn’t reply because I was enjoying the sensation too much and just moaned a bit. She was pleased by it so she continued. In and out she went with her fingers, spreading them, twisting them, finger fucking my hole. After a few minutes, she took some more lube and spread it across her fingers again. She now teased my ass with three of her fingers. Now there was some resistance and she couldn’t push them in. So she started teasing again a bit, circling around the hole, putting in two fingers then tried sliding in the third one a bit. She was slowly making process, stretching my ass trying to accommodate her fingers. She managed to put them in about two-thirds of the length and she was satisfied with the process.

“Now on to better things.” she teased.

She took the small blue dildo which was about 6 inches long and about 3 inches around. It went in without any resistance. She didn’t remove it but started fucking me with it. In and out it went for several minutes. Then she switched to a medium-sized pink dildo, which was about 8 inches long and about 5-5.5 inches around. She teased my butthole a bit first then started pushing in. She was doing it really slow and moved it in little by little. She slowly inserted the head and stopped.

“Try to relax a bit, take a few deep breaths and relax.” she said calmly.

When my breathing calmed down she slowly pushed it in a bit more. About 3 inches later she stopped and started pulling out. She didn’t pull it out all the way but stopped at the middle of the dildos head. Then slowly back in again about 3 inches.

“I feel very full right now. And this is not even big.” I said feeling a bit down.

“No worries, we all started somewhere. If we can’t make it then I won’t stick mine in you today. Don’t think about it at all and just relax and enjoy the feeling.” she replied in a soothing voice.

I took a few deep breaths and motioned her to continue. She pushed it in another inch then took it completely out. I felt a brush of “cold” air in my ass. She took some more lube and spread it on the dildo and my hole with her fingers. She then positioned the dildo at the entrance and pushed it in a bit faster now. I felt a slight rush of pain but it subsided almost instantly as the dildo’s head entered my body. She moved it in about 4 inches again then almost out and in again. She started fucking my ass, slowly at first then sped up. A few times she took it completely out, waited a few seconds or not at all, and pushed it back in. I started to enjoy the feeling of fullness and she was fucking my ass faster and faster now. She was brushing my prostate with the dildo and the mix of both sensations was making me wild. I was unwillingly moaning like some chick in a porn movie and I saw a spark in her eyes.

“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