The Meeting Pt. 02

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Girl meets with shemale for kinky hotel sex.
4.1k words
4.58
12.5k
13

Part 2 of the 3 part series

Updated 06/10/2023
Created 06/04/2020
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If you haven't read part 1 that's fine, this story would probably make more sense but I think you could enjoy it as a stand alone.

Saturday couldn't come soon enough. After the incredible experience I'd shared with my boss, Gregg, and the beautiful Asian shemale, Motoko, I was very excited to see them again. Well I saw Gregg again pretty quickly as I went to work on Friday but I tried my best to avoid him. I didn't want people to suspect anything, it was a small company and rumors could destroy my reputation.

By the time Saturday afternoon came I was quite anxious as I got ready. I was never the type of girl who wore tons of makeup and my wardrobe was on the conservative side but I did my best to make myself look desirable. I wore my shortest skirt with a low cut v-neck shirt. I didn't own any lingerie but if I had I would have worn it, instead I put on a lace bralette and the only thong I owned, they didn't match but I didn't care.

I eagerly drove to the hotel that Motoko had told us she was staying at. When I went through to the lobby the look the clerk gave me confirmed that I had succeeded in looking desirable. The lust in his eyes could burn a hole in me if I wasn't careful. "I'm here to visit my friend, Motoko Ayasowa, she's staying in room 416." I told him. He looked down at his computer and typed something.

"Yes, you must be Ms Shields. She let us know to expect you. The elevator is behind you on, she's on the 4th floor and to left after you get off the elevator." He informed me.

"Thank you." I said, smiling at him as I turned toward the elevator doors.

I had no problem finding the room, it was right where the clerk said it would be. I took a moment to prepare myself, I took one last look at myself in a mirror in the hallway, my hair and makeup looked fine so I knocked on the door. Seconds later I was greeted by Motoko, she had on a silk gown bath robe with a lovely floral design and she had a glass of wine in her hand.

"Ms Shields, Molly, I'm so glad you decided to come, I wasn't sure you really would." She looked a little surprised but happy to see me. "Come in, come in." She gestured for me to enter.

"Thank you." I said quicker than I intended, I was more nervous than I thought I was. I stepped past her and into the room, it was a lot nicer than what I was expecting, the bed was a king size and there was a leather sofa along with a mini bar. Higher end than the hotels I was used to.

"Would you like a glass of wine?" She said casually as she closed the door and walked over to the mini bar.

"Oh, no thank you. I'm fine." I said. She topped off her glass and sat down on the sofa. She was so elegant, even sitting down she confidently leaned back and crossed her legs with her wine in her hand she was so sexy.

"Please, sit with me." She patted the spot next to her and I moved over and sat with her. "We have some time before Mr Bailey, I mean Gregg gets here and I'd like to get to know each other better." She said and then took a sip of wine.

"Sure, what would you like to know?" I said, getting comfortable on the sofa.

"Where are you from? Where did you go to school?" She paused, "How many boyfriends have you had?"

I let a small laugh escape me. "I'm from right here in Hartford, I went to community college and I've had 3 boyfriends." I said.

She looked at me for a second before saying anything. "You're not a virgin but you have very little sexual experience, I could tell you'd never had your pussy eaten before, you'd also probably never been with another woman before." She sounded confident in the way she said it, it helped that she was totally right.

"But you're not a woman." I said and instantly regretted. She didn't look offended like I'd feared.

"Why? Because I have a penis? I'm still just as much of a woman as you are dear." She took another sip of her wine.

"I'm sorry, I didn't mean anything by it." I apologized.

"It's quite alright, I'm very comfortable in my skin, that's something I want to help you with, I love helping innocent girls like you find out more about yourselves. Tell me, do you have any experience with anal sex?" She looked at me with an inquisitive smile.

"No, I've never had anyone do anything like that with me." I said while blushing, I was expecting sex to come up in the conversation but not this quickly.

"Well, we're going to have to change that." She said and stood up and walked over to the bedside table. She opened the drawer and pulled out two things. When she turned I realized what they were. She was holding a bottle of lube and a shiny metal butt plug.

"Bend over the couch." She told me, she sounded polite yet forceful. I couldn't help but comply, I got on my knees, still on the sofa and faced the wall and bent over it, my butt in the air facing her.

"Excellent, it's important that you relax for this part." She sauntered over and placed the lube and plug on the seat next to me. She then pulled my skirt up and began slowly rubbing my pussy through my thong, she began to tease me with her tongue over the edge of my underwear. If her goal was to relax me she was succeeding. I let out a small moan and I could feel her fingers starting to pull the thong out of the way, she wasn't removing it just moving it to the side. My pussy was exposed and so was my asshole. She slid her fingers back into my moistened pussy and licked me in long strokes, her tongue reaching higher each lick until her tongue was hinting on the outside of my asshole.

She continued for a while like that with her tongue roaming my underside with her fingers caressing me until her hand pulled out of my vagina and started probing my butt. It was gentle at first, just a little poke alongside her tongue, but I could feel her fingers start to apply more pressure until they penetrated my asshole. I was trying to remain calm but I was not expecting it to feel the way it did, it was strange but I was enjoying it.

To her credit, Motoko was making her best efforts to soothe me, she whispered how it was going to be okay and that I was doing great. I didn't notice when she picked up the bottle of lube and began applying it directly to my asshole and her fingers. This helped a lot with my discomfort, her fingers were now gliding through me with much less resistance and it was actually starting to feel good. Eventually she withdrew her fingers and I looked over my shoulder to see her getting lube on the butt plug, she gave me a reassuring look before moving back to my rear. Unlike her fingers which were warm, this metal plug was very cold, it was also a lot wider than just her fingers but she went slow and there was a lot of lube involved so it did make its way in. Once it passed the apex of the plugs width I felt a wave of relief as the plug was all the way in.

"That's a good girl." Motoko said as she leaned back, "Now I want you to get up and move around, get used to the feeling of having your ass filled." I hesitantly got up and smoothed my skirt and then slid my thong back into place. The plug made everything difficult. I noticed right away how hypersensitive I was feeling whenever I took a step, it was grinding in my ass the whole way. Motoko watched me and smiled as I got used to walking again. "Perfect, now come over here, I have something else for you." I walked to where she had sat down on the edge of the bed, she slid the belt of her robe out of the way and she pulled herself free of it. Her skin was smooth and flawless, her D cup breasts and her semi erect penis were on full display.

We embraced gently with each other, her lips found mine and we shared a deep kiss, she pulled my shirt up over my head and we parted briefly but then her lips were back, kissing me harder. I felt her reach around and unhook my bra and pull it from my shoulders. Our naked breasts pushed up against each other as we continued to make out, my hands started to wander. She had beautiful boobs, there was nothing unnatural about them, they didn't feel like they were silicone, they felt just like mine. I cupped them for a bit and felt her nipples harden. She was enjoying it too, as we kissed she explored my body. Her hands on either side of my hips, her penis rubbed against my stomach. We were enthralled with each other for what felt like minutes before she broke the spell.

She put her hands on my shoulders and held me at arms length. "I want to teach you how to suck a man's cock. Properly, not the sloppy mess you gave Gregg. While I will give you points for effort it looked like that was the first time you ever had a penis in your mouth." Her words were stern but there was a tenderness behind them.

"That's because it was the first time. I've had boyfriends ask me to do it but I always refused." I told her. "But I think it's time I learned."

She smiled at me and told me to get on my knees. I pulled back and lowered myself to the floor in front of where she sat on the edge of the bed. I was face to face with her monstrosity of a penis. "How about you just do what feels natural and I'll tell you what's good and what's bad." Motoko spoke down at me. I took her member in my hand and gave it a few strokes. I held both my hands on it, one above the other but it was longer than both hands put together. I jerked it for a few seconds before I tried to take it all in my mouth. I got little more than the head of her penis in before she stopped me.

"Use your tongue. Get it all wet before you put it in your mouth. Start from the balls and work your way up. It's fine if you keep stroking but unless you want me to cum quickly you need to lessen the pace." She pulled her cock out of my mouth and held the tip of it up so her balls were exposed. I did as she asked and started licking her testicles, holding them up with just my tongue before licking the base of her shaft. I ran my tongue up the underside of her penis and I licked the top of it on my way down. I did this about 4 times before she was nice and wet, so was my hand from where I was pumping her.

I decided that I was ready to take her in my mouth. It was much easier to take her in with it already being slippery, I got her deeper into my mouth then I had before. I got her all the way to the back of my throat before retracting, I pulled her all the way out and bobbed my head back down. I was only getting about a third of her snake in my mouth.

"Dear, that is a very basic way to give a blowjob, it should be enough to please most men but it's not enough for me. You need to take my cock down your throat if you want to make me cum. Try putting the tip as far as you can and then swallow. You'll probably gag a few times but the more you do it the easier it becomes." She instructed me. I took her advice and rested her penis in my mouth with the head as deep in as was comfortable. Unsure of what would happen I hesitated briefly, I looked up at Motoko who smiled and said. "You can do it. I believe in you."

I took a big gulp and her cock forced itself down my throat. She let out a moan but I couldn't take it. I ejected her penis from my mouth and gagged. I'm surprised that I didn't throw up on the hotel carpet. Motoko knelt down and put her hands on my shoulders in a comforting way. "That was great, Molly, you did so well. The ability to deep throat is what separates the girls from the Queens. You're a natural. I want you to try a few more times, until you don't feel like throwing up." She got back up and once again I was staring down her massive tool.

This time I wasn't going to let it win, that cock was going down my throat one way or another. I lifted it with my left hand while I put my right hand on her butt to hold us both in place. I opened my mouth and took her cock back to the threshold of my throat and put my other hand on the other side of her butt. I swallowed with all the force I could. I pulled her cock in as deep as it would go. The sound of her moans filled the room and she started to thrust ever so gently, swaying her hips to reach greater depth. I held her cock in my throat as long as I could, what was probably 6 seconds felt like 6 minutes. My eyes had completely teared up by the time I backed my head off of her. I took a moment to catch my breath.

"I'm so impressed with your tenacity, Molly, it took me much longer than that to deep throat when I first learned to suck cock. Take a breath but keep going. There are few feelings more satisfying than making someone cum with just your mouth and throat." She positively beamed at me. I really wanted to take her over the edge and have her cum in my mouth.

I gripped her slimy cock and licked it all over. My hands and face had saliva smeared all over. I stuck my tongue against the head of her penis and got a taste of her salty pre cum, after lapping it up I plunged her whole cock in my mouth. I worked it good in my mouth while also rubbing her shaft with my fingers. I positioned her ready to go down my throat and swallowed, at the same time I tugged on her ball sack. She screamed as I felt her convulse in my mouth and suddenly wave after wave of cum rocketed down my throat straight into my stomach. Her furious grunting slowed down and she pulled her cock out of my mouth. It was still spurting on the way up and I got a mouthful of seed as well as a small spatter on my chin.

She pulled me up from my knees and onto the bed with her. She licked the cum from my chin and her lips went for mine. As we kissed her cum was passed back and forth, from my mouth to her mouth back to my mouth. I felt her reach down and pull my thong free from under my skirt. She balled it up and threw it across the room. I was a bit confused but it was short lived as her hand quickly moved back between my thighs and up to my soaking vagina.

Her fingers danced around my entrance, teasing me for what felt like forever before she let one finger breach the gap. She then slipped a second finger in me and the two of them started spreading my pussy wide open. She teased me more as our lips remained locked. Between the two of us most of her cum had been swallowed or lost but the taste was still there on her lips.

She was the one who finally broke our embrace. Pulling her hand from beneath my skirt she got up and turned, giving me a view of her rear. It was when she turned around that I realized that she was also wearing a butt plug.I looked up at her and she winked at me. "You never know when you'll need to be ready to take it in that back door." I laughed a bit at how casual she was about it.

"Were you wearing this Thursday when you came by the office?" I asked.

"Of course, dear. I try to wear them as often as possible. It is hard getting the metal ones passed airport security, I own one rubber plug for specifically that." She said. I couldn't control my laughter at all this time, it was contagious too because Motoko started laughing. "It's not that weird, plenty of people own sex toys. Quit laughing." She said while also laughing herself.

After a minute or so I looked back up and asked her, "Can I see your toy collection?"

"Sure, dear. I don't travel with all of them but I do have plenty on me." She walked around the bed and pulled out a small purple suitcase that still had the luggage tag from the airport. She unzipped it and I saw the treasure trove of sex toys, she had multiple dildos of various sizes, colors and materials. There was a rabbit vibrator, there were more butt plugs, she had a ball gag and a few leather paddles. There was a set of anal beads and what looked like a fake vagina. I only knew what half of it even was, I had no real experience with sex toys before.

"You said this isn't your whole collection but there's so many toys here, I can't imagine how big your collection is." I said while reaching for one of the dildos, it was very long with a penis head at either end.

"I'm something of a collector, whenever I travel to a new city I always buy sex toys as a souvenir, I picked up that double dildo in new York, I've yet to use it with someone else, would you like to help me break it in?" She said seductively. I wasn't sure how someone would use it but my interest was piqued.

"How would we use it?" I asked

"We'll each have an end inside of us and we rock back and forth, simulating sex. It's a very sensual experience for two women to share." She said while taking the dildo. "Get on the bed and spread your legs."

I did as she asked, then looked over and saw Motoko administering lube to the double dildo, before joining me on the bed. She positioned herself between my legs and went down to lick my pussy. Her tongue flicked across my outer lips as she slowly started to remove my butt plug. I shuddered as the thickest part passed. Still licking my sensitive bits she started working more lube into my ass.

I was a bit confused as I thought the dildo would go into my vagina but I was enjoying her tongue so much I couldn't think straight. I felt the tip of the dildo enter my ass, the greased up rubber cock invading my hole and stretching it more than I'd ever experienced. Motoko went slow at first but she went quite deep with it before she slowly pulled it out until just the tip remained inside me before thrusting it back. She repeated this a few times, gaining speed with each thrust until pain became pleasure. I started moaning harder and she could tell I was enjoying myself.

Eventually she leaned back, taking her lips off my pussy but leaving the rubber cock. I watched her remove her butt plug, it must have been twice the size of the one she put in me. She lubed up the other end of the dildo and her ass before she slid right onto the thing. I was amazed at how easy it was for her. She got it deep and she adjusted herself so we were lined up with our legs tied up like a scissor. Her cock was hard and aiming for the sky as we figured out a rhythm of humping that made the dildo between us thrust on its own. The sound of our moans soon drowned out the sound of the bed springs squeaking and the splashes coming from the lubed up dildo in our assholes. I reached down and started rubbing my pussy and she started jerking her cock as we humped against each other. My orgasm was getting closer and closer before Motoko stopped. She leaned forward and shifted her legs behind her. She positioned herself between my legs once again, the dildo still inside both of us. She slapped her cock down against my pussy and I realized why she put the dildo in my butt and not my vagina. I took her big dick in my hand and positioned it against my opening and the tip slid in before either of us knew it. I was so wet from the dildo and the humping that she had no resistance sliding all the way in.

Yet another new experience, double penetration was never something I'd ever even thought about until it was happening to me. I felt so full as her cocks impaled me. She was thrusting in such a way that I was being fucked by both of them at the same time. She pushed forward and kissed me as her hips grinded and our boobs rubbed together. Her hands held my pelvis for leverage as she pounded me. It didn't take long for me to start orgasming. The sound of my ecstasy was enough to set her over the edge too as I felt her penis pulse as she deposited wave after wave of the biggest cum load I'd ever felt into my quivering pussy.

She just kept thrusting as her seed splashed everywhere. I could feel it dropping down my thighs. After what must have been 30 seconds of cumming Motoko finally started to slow her pace. I felt the snake she called her penis slip out from my vagina. She hovered over me and jerked a few final drops of cum onto my stomach. The double dildo had flopped from her rear onto the bed, one end still inside of me.

Our labored breathing was the only sound you could hear. I looked down at the lake that was my vagina, I'd never seen so much cum in my life. If you had told me that 10 men had just ejaculated in me I would have believed you. Motoko reached a hand down and scooped up a handful of spunk and brought it to her lips. She made eye contact with me and slurped it all up. Then she crawled up to where I was lying, I felt her breasts and her softening penis rub against me. When she got next to me she leaned over and kissed me, giving me another mouthful of her cum. We didn't play with it as long this time but it was still an incredibly sexy act that felt very intimate.

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