A New “Pretty Woman”… Pt. 01

Big Tits

All this And A Pretty Woman Too

It was a Friday night, and per usual at this time of Covid, I was at home, surfing the net, playing some games, and listening to the telly in the background after working all day. My musical mates had been online and we were chatting for several hours about songs, lyrics, and chords after our respective dinners. My housemates were either out at their girlfriend’s or just in their rooms. I was feeling rather “frisky” and decided to see what “mischief” I could get into. So, I pulled up an “escort” site on the internet that one of my music-mates told me about and perused the photos and brief descriptions of the services the ladies were offering. As I scanned the articles and face/body photographs, there was one that intrigued me. She was young and very fit with multi-coloured hair, but what really drew my attention was all the ink she was sporting. Her hands, neck, back, and of course arms and legs, were decorated beautifully. Additionally, there was something about the look in her eyes: and intense and piercing look that immediately got me curious. In her description, she said that she would be someone that “actually fucks like a whore and actually looks hotter in person”. Also that “weird fetishes and extreme kinks are accepted. I’m both experienced at being the dominant AND submissive, so take advantage of all my talents”. Understandably, her number was there and so I rang it up at once. She didn’t answer, and my call went to her voicemail. I introduced myself, and asked if she had some time available to see me and how many “roses” I should bring. After hanging up, I texted her the same information, in case she didn’t check her voicemail regularly, but would see my text. I then went back to my games, surfing and telly listening.

After quite a while, my phone “dinged” telling me that I had a text. But it was a surprise.

“I’m Aliyah, Raven’s not around,” the text read, “would you like to see me, I have my own room.”

Included with the text were three photos of Aliyah: dark hair, not as slim as Raven, black lingerie, but very pretty with nose and left nipple piercing and a couple of tats. She also sent a short video of herself in the same lingerie, pulling it aside to show her tits and moving the (I suppose) phone around to give a panoramic view of her body, smile (a great one) and surroundings. I had some trouble getting or keeping an erection and even some difficulty cumming, so I wanted this first time with an escort in over 5 years to be worthwhile.

“Thank you for these, I absolutely love them!” I texted back, “I would definitely come to see you, there’s just one thing. It’s nearly midnight now, and it’s been a long day. Plus, I live about a half-hour away and maybe we could do something tomorrow.”

“Are you sure you can’t make it tonight?” she replied, sounding disappointed, “I’m a night-owl, you see, but I can definitely make time for you tomorrow sweetheart.”

“Quite honestly,” my answer came, “I’m exhausted. It’s been a tough week and all I want to do is just crash into bed at this point. But you are absolutely gorgeous and I would love to see you tomorrow.”

“Awesome,” she said back, “I’m actually excited then.” Followed by two cute emoji’s. I loved her enthusiasm and spirit straightaway. “Do you like lingerie, etc.? I love to dress up and stuff, Lmk what kind of things you like and I’ll make it happen.” Three more emoji’s! Too cute!!

I went on to briefly explain that I did like lingerie, but not shoes or stockings. I also like to “go slow” and take my time. Kissing, romance, and laughing are definitely turn-ons for me as well. And maybe we could have an “extended time” together? I also sent her two photos of me that I had on my phone.

“If I was excited before, babe,” she texted, “I really am now. Oh, and I rarely wear shoes and I love to laugh. Of course, I would love to be with you for however long you want hun. WOW.”

“OK, Aliyah,” I said, “I’ll ring you up in the morning and set things up for noon-time, then.”

“Night, night, babe,” she replied, “Can’t wait.”

“G’night,” and set the phone down and excitedly went right to sleep.

The next morning and I showered, dressed quickly and picked up my phone, there was a text from a number that I didn’t know.

“Hi Kevin, this is Aliyah,” read the text, “my phone is fucked up and I’m borrowing a girlfriend’s. Do you still want to get together?”

This time, rather than text, I rang her up.

“Hell-ll-llo,” came the voice pleasantly on the other line, “Kevin?”

“Hiya, Aliyah,” I said back, “yep, it’s me. You’re up early for a night-owl. So, does noon-time still work for you?”

“Yes,” came the quick reply, “I’ve been thinking about it all morning and it’s only 10:00!” And giggled enthusiastically.

We chatted for a bit: “I’m really oral.” I told her. “Ooh, good, so am I” she replied, and we agreed on a “donation” for 2 hours together. It was more than I had anticipated, Travesti but I figured, what the fuck. It’s only money. And sounding as she did with her bubbly nature and incredibly sweet personality, this might be really fun.

I got to the hotel she told me and then rang her up again in the car park.

“I’m in room… let me see on the key,” she answered, “I’m so disorganised. Room 113. I’m so looking forward to this, Kevin.”

I left my car, as well as my wallet and phone inside, locked it, went inside and found Room 113. The only thing was that the bed was stripped and the room was empty! “Aw shite,” I thought, “really? What the fuck!”

I went back to the car and rang her up again.

“Hell-ll-llo”, she answered merrily.

“Did you say 113?” I asked, “there’s no one there.”

“Wait a minute, wait a minute, let me check the door,” she said, “Oh it’s 123. I should have remembered that.”

“All right,” I said, “I’ll be right there.” Well, this is starting off well… NOT!

It was just down the hall and she answered the door wearing only the same cute lingerie as in the photos and video. She was short with a nice figure (initially I thought a little heavier than I normally like) and much prettier than even in the photos sent to me. She immediately turned to me, after locking the door, threw her arms around my neck and kissed me full on the lips which I returned with vigour as I held her around her waist. I had only ever been with a couple of “escorts” but they didn’t behave like this.

“You do like to kiss don’t you,” she said, “that is so cool.” And we did it again. My hands roaming over her back and the lingerie-covered arse. She turned around in front of me and I kissed her neck and massaged her breasts, at first over the lingerie and then she pulled it aside as she had done in the video and fondled her breasts and left-pierced nipple. She reached around and held me around the neck again, thrusting her arse against my trousers.

“I’m sorry,” she said, gently removing herself from around me, “I hate to do this, but do you have the donation? That’s partly how I pay my bills.” I put the agreed amount on the nightstand. Without counting it, she put in into her purse and as she turned, I read the tattoo on her right shoulder: “Aliyah”. “I’ve got to get a new phone, and finish the paying my mortgage, so that is where this is going straightaway.”

“Partly,” I asked as we re-connected, arms around each other facing one another, “what do you do for work?”

“I’m a hairdresser,” she said and we kissed again, her lowering and stepping out of the lingerie. “I went to school for it and am working, just started doing this in hopes of getting more income.”

She then moved to the bed and lowered the covers as I got as naked as she was. To my surprise, my member was standing at attention already. Aliyah then crawled to the middle of the bed and got on her hands and knees.

“Well,” she said, looking at my erection, “that certainly looks nice.”

I got on the bed and laid down, gently pulling her next to me as we kissed and fondled each other. I tweaked her nipples including the left, pierced one, and sucked on them. She reached down and was stroking my erection as I reached down and felt the dewy wetness of her pussy. It was then that I noticed the piercing very close to her clit.

“So, what things are you into,” I asked her and kept massaging her body.

“Well, I love doggie-style and love to have my arse slapped,” she said, continuing to stroke me “and I like things rough, but not too rough, or easy. I pretty much…”

“Go with the flow,” I finished her sentence, “yeah, that’s me as well.” I then sat up on my knees and pulled her legs apart until I was sat between them. Her vagina was wet, but not fully open yet. “I told you I was very oral.” And I dived between her legs and inserted my tongue into her vagina.

She moaned and asked, “Can I use a toy whilst you do that? It makes me cum so hard when I play with myself and am eaten out.”

“That’s so fuckin’ cool,” I said enthusiastically, “I haven’t seen someone use a toy in about 2 years. Be my guest.” And she reached over to the nightstand and got a six-inch long vibrator, which she turned on and put on her clitoris as I was licking and rubbing it with my tongue. Shortly as she continued to moan and move around the bed, “Fuck, fuck, fuck,” I took hold of the vibrator from her and put it on her button, rubbing it around periodically. “Oh fuck,” she said as her excitement grew, “Come on babe, cum for me, Aliyah,” I urged and kept on licking and vibrating. Her legs flew wide apart and her toes clenched and unclenched unconsciously. After only a few more seconds, she lifted her hips off the mattress and came in my mouth, letting out a loud moan of ecstasy. I moved up and kissed her again on the mouth, which she eagerly returned and hugged me around the neck again, entangling our bodies on the bed. She moved her hips so that my still hard Ankara Travesti (surprisingly) erection was against her clit, and kept moving back and forth so that she was constantly rubbing her clit on my engorgement. I was understandably pleased that my member was cooperating so well.

“I have some condoms in the drawer if you want to go inside me,” she said between kisses and continuing her rubbing, and I didn’t reply but kept kissing and sucking her neck, “but you don’t like condoms I see.”

I looked at her knowing that she understood what I was thinking, “I got a physical and blood-testing two weeks ago, and everything came out clean,” I told her honestly.

“Is that true,” she asked, “really be honest.”

“No,” I answered, “I am. You’ll find that I am always honest… to a fault.”

“I usually only go with a condom, but all right,” she said and rolled on her back, spreading her legs. I eagerly got between her thighs and grab hold of my (incredibly) still hard-on. I rubbed it up and down on her clit, teasing it to erection again, causing Aliyah to moan anew and her pussy to get even wetter.

At this point, I decided to see what she actually was into. So I thought I’d try a little role play:

“You know, I saw what you wrote on the inside of your thighs as you sat in front of my class,” I told her, “it said ‘Fuck Me’ didn’t it?” I was still rubbing her clit with my erection, occasionally moving between her ample labia.

“Yes it did. I knew you saw that,” she breathed, catching on straightaway, “I wore that skirt just for you.”

“And you purposely sat right there in front didn’t you,” I asked her as my member got even harder. I had never dared approach this taboo fantasy with anyone else, but Aliyah was so nice, friendly, and sweet, that I thought I’d give it a go.

“Yes, I did,” she told me, “and you know why? Cause you turned me on, and I knew you were watching me and it was turning you on.”

I re-positioned myself right at her entrance. “What do you want me to do to you? What did your thighs say?” I asked.

“Fuck me,” she said and licked her fingers, then put them to her open gash for lubrication.

“What do you want me to do, Aliyah?”

“Fuck me, Kevin, fuck me.”

I inserted my entire length into her and she moaned loudly as she held her pussy open with her fingers as I did so.

“Oh fuck,” she let out, “that feels so fuckin’ good. I love your cock. It’s not too big and not too small, just right for me.” And she moved her hips rhythmically with mine, holding my hips with her hands and spreading her legs wide apart. “I knew you wanted me, I could tell by your eyes… the way you looked at me.” Keeping up the story line.

“What did I look like,” I asked, thrusting in and out of her warm depths.

“Like you wanted to fuck me,” she said, breathing hard and nearing her climax.

“I tried not to be too obvious, but dressing like you did, with those meshey tops and either mini shorts or skirts, what did you expect?” I kept pistoning in and out of her, feeling her getting tense in anticipation of her orgasm.

“I wore them only for you, you know,” she said between breaths, “this pussy is yours, Kevin.”

“Whose pussy is this?” I asked, (miraculously) maintaining my erection as we kept fucking.

“It’s yours, always yours, only yours,” she said, lifting her hips again. I leaned back on my knees and toes, my hands on her knees to keep her from lifting off the mattress completely and kept pumping until with a “fuck, fuck, FUCK!” and an encouraging, “Cum on my dick, baby, cum on me. C’mon on,” she did just that. After she had calmed down a bit, I pulled out and lay next to her.

“Did you cum too,” she asked.

“No, I can wait,” I told her, not revealing that for some reason I had trouble in that particular area. But here again, my member was still hard, but gradually going down.

“So, do you do this often,” she asked me, starting to put her hand on my shoulder again and looking me right in the eye. “By the way, you have really intense eyes, Kenny.”

“No, it’s been a long time,” I told her, “I know, you’re not the first to tell me that. What about you? Do you have many… clients?”

“Sure that’s what they all say,” she teased me, “and no, as I said, I just started doing this and I don’t want more than one maybe two friends that I’ll be with. I’m not an official escort, I just do this for some more income. Do you want to be that one?” And she kissed me gently this time. I could feel my erection start to grow again.

“I’ll be that guy,” I said with great enthusiasm, and pointed to myself with my left hand. “I definitely want to get together regularly, and maybe spend overnight and/or cooking together. You said you are a good cook, so am I.”

“I am, I’m a great cook and that sounds like so much fun,” she said with equal enthusiasm, “I would love to see you… and… not as a client, if you want. And overnight would be great!”

“I istanbul Travesti would like that a lot,” I said then kissed Aliyah and held her tight to me. Our arms were around each other and our bodies were enmeshed when she put her right leg over my legs. I slapped the right cheek of her arse and she let out a little “oh!” Once we kissed several more small kisses, I grabbed her right leg and disentangled myself from her, remembering what she said earlier. I semi-roughly turned her over onto her stomach and pulled her hips to me. I hadn’t done “doggie” in a long time owing to the inconsistent nature of my organ, but thus far it was seeming to cooperate beautifully. Again I teased her pussy with my erection, and again she moaned naturally and loudly. I slapped her arse again, and inserted myself into her wet, waiting and open canal. She moaned and grabbed the sheet on the bed. Over and over I thrust into her, spanking her left buttock, then her right, then both at once as she continued to squirm, moan and swear with every action.

“You always wanted to be my slutty little student, didn’t you,” I asked her, back in role-play mode that we both seemed to enjoy so much.

“Yes, yes, I wanted to be your slutty little student, since the first day in class,” she said, going right along, “this is your pussy. I wanted to give it to you, and now I am. I love your cock. FUCK ME!” And I did with even more vigour and kept slapping her arse as well, pulling her hips back and forth, so that I was balls-deep into her opening.

“Do you want me to play with myself whilst you fuck me,” she asked.

“Yes, I do, Aliyah,” I replied, “I want you to cum all over my cock again, like the little slutty student that you are.”

“Oh… my… god” she said into the mattress, and proceeded to mover her left hand underneath her body and play with her clit. Every so often, massaging my balls as well, so that in short order, she came on me for the second time and collapsed on the bed. Amazingly, I was still hard, which hadn’t happened since college days.

I rolled her over onto her back and lay down next to her again and we looked into each other’s eyes as we held each other.

“Do you like dressing up also,” she asked and rolled on top of me.

“Yeah, but I think the only thing I could possibly dress up as is a professor,” I told her, “however, I’m open to any other ideas, babe… go with the flow.” She giggled and kissed and sucked my neck as I kissed and bit hers, at which she moaned deeply. Then she bit mine. As we were entwined and kissed, I licked her chin with my tongue and Aliyah licked my nose with hers. Now it was my turn to let out a little “oh”.

“You like that,” she asked, and quickly licked my cheek at which I gave another little “oh… yes”. It was a new turn-on for me that we both discovered at the same time. No one had ever done that to me before. “I told you I was oral as well,” she reminded me, not that I had forgotten. We smiled genuinely at each other and kissed deeply once more. She then moved down and grabbed my erection again and gently put it into her mouth. She started sucking and slurping at a rapid pace.

“No, babe,” I said to her, “could you go slowly?” At once, she slowed down to a pace that amplified each and every feeling of her suction on me. I was in ecstasy and she was the reason. After a time, I reached down and held her shoulders and pulled her up to my face to kiss some more.

“I’m so fuckin’ glad you texted me,” I told her, looking into her eyes.

“You have no idea how glad I am as well, Kevin,” she told me returning my gaze and kissing me deeply again.

“Would you get on top,” I suggested. And she moved slightly back and got on her feet, crouching over my mouth-slathered organ. She reached down and grabbed a hold, putting the phallus at the opening of her vagina. Again, she teased herself, rolling her head back before sitting on me fully. She bounced up and down in her crouched position a couple of times and then pulled her legs in front of her parallel with my chest, and now in a more comfortable position, rocked back and forth so her clitoris was getting massaged at the same time as her pussy was being fucked. The bed had apparently shifted and was now banging against the wall with every movement. Somehow it didn’t seem to affect either of us.

“Whose pussy is this,” I asked and rubbed her clit that was facing me, causing her head to roll back again.

“It’s your fuckin’ pussy, Kevin,” she said ecstatically, “you know it’s all yours. I’m just a slut for you, you know. It’s all I fuckin’ want.” And she continued rocking on my member and getting herself off again. “You turned me on on the first day of classes. I just knew that I turned you on too.”

“You did,” I played on, “and that’s why you sat in the front row isn’t it?”

“Yes,” she said immediately.

“So that no one could see that you never wore nickers or a bra, isn’t it?”

“Yes, just to your class,” getting more and more excited.

“That’s why you sat right in the middle of the front row, and spread your legs apart isn’t it?”

“Yes, yes it was.”

“That’s why you wrote all those things on the inside of your thighs every class, isn’t it?”

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