Traveling Ch. 04

Chapter 4 -- Online Meeting

Having to spend a week in Austin, I decided to try a popular adult dating site and see if I could find a playmate for the week, or at least a few nights. I found one that sounded promising, the ad read "somewhat submissive female wants to try wild side". The ad listed her as '38, nice looking, five foot eight inches, about 135, curvy in the hips and butt, with 38E breasts, reddish blonde hair and pale complexion.' It went on to say she was interested in 'light bondage, spanking and maybe anal,' and wrapped up with 'discretion is a must.'

I responded that I was very interested in helping her explore her wild side, gave her my stats and mentioned that begin from out of town there was little risk of us running into each other or me exploiting her in any way. Much to my surprise, I got a response the next morning. We chatted via email and then finally spoke on the phone the day before I was to arrive in Austin and agreed to meet the following night at the Mexican food restaurant next door to my hotel. She said that she had a boyfriend who was disgusted by the thought of anal sex and was not much into bondage or spanking, or anything else that she thought might be fun. We decided that we would do some spanking, some bondage, and some fucking, both pussy and ass. She agreed to let me cum in her ass, but I had to wear a condom when fucking her pussy. After we agreed to the plan, she then said that her real name was Melissa and that she would be wearing an emerald green dress, white stockings and matching heels.

After arriving in Austin and having had my first round of meetings, I headed to a local adult store and picked up a leather strap paddle, which was two inches wide and only about an eighth of an inch thick, and about six inches long with a slim handle that could easily double as an anal toy. I then bought four silk scarves to use as ties. I also bought flavored condoms and a tube of anal lube and a four inch long butt plug.

After dropping the items off at my hotel and a quick shower, I headed to the restaurant and sat at the bar waiting on Melissa to arrive. She was about 10 minutes late, but she did show up. She was exactly as she had described herself, if not actually better looking than she had described. Her emerald green dress came to about three inches above her knees, and her legs were covered in white nylon, she had on emerald green heels that matched the dress. Her reddish blonde hair cascaded over her shoulders. Her hips flared slightly, showing that she had a plump ass and hips. Her tummy didn't appear flat, but wasn't a washboard either. Her breasts were large and spilled out of the top of her pushup bra, which caused her breasts to be very pleasing to the eyes with the dress low cut in the front.

I gave her a wave and she smiled and walked to me. We chatted for a minute while the waitress got our booth ready and the bartender mixed her a margarita. At the table we chatted more, drank a few more margaritas and then she said, "well, what now?"

I smiled and said, "Well, I think we should see if you are really serious. What kind of panties are you wearing?" I asked.

She blushed, her cheeks glowing bright red, "I have on a green thong that is silk with black lace trim."

"Are your nylons full pantyhose or stockings?"

"Stockings," she replied, her face still bright red, but her green eyes staring intently into mine.

"Good," I said. Then ordered, "Slip them off and hand them to me."

"HERE?" she squeaked.

"Yes," I said quietly, "Right here and right now."

She giggled, then both her hands disappeared under the table and she began fidgeting around. After an uncomfortable minute or so, she brought her cupped hands up onto the table and slid her closed fist to me.

"Open your hand and show me," I said.

Her face darkened again, a cute smile on her lips, as she opened the hand and showed me a very sexy green silk and black lace thong.

"Just lay them right there," I said.

She smiled as she dropped them on the table and adjusted herself. The waitress dropped of our fresh margaritas and could clearly see the panties on the table, she smiled at both of us and walked off.

"OH MY GOSH!" Melissa said, grinning from ear to ear, her face still bright red, "She must think we're nuts!"

"I bet she's thinking that you are one hot woman, same thing I'm thinking!" I said.

I picked up her thong and brought it to my nose. The center was damp, indicating that she was obviously excited. I inhaled the scent which was sweet and clean smelling. She was blushing deeply again as I slid the thong into my jeans pocket.

"Now, Melissa, does your bra match your thong?"

Grinning, "Yes, it does."

I smiled back, "Cool, why don't you go to the restroom and take it off and then bring it to me."

"Seriously?" She said, looking around the restaurant to make sure no one could hear us.

"Of course!" I replied.

"But my boobs are huge and my nipples are so hard that they ache! Everyone in here will be able to see me!"

"I know, but you have to show me that you are truly my submissive slut tonight. So, go take off the bra and bring it back to me." I smiled as I said this to her.

She sighed, then smiled big and said, "Okay, but I'll need to take my purse so put it in, since it is pretty big."

"Works for me!" I replied.

She then slid out of the booth and started to leave, I reached for her arm and pulled her to me. She bent slightly and I smiled and pulled her closer. She got the hint and leaned in and kissed me.

Her lips were soft and sweet and she sighed as I kissed her, my tongue dancing with hers. I broke the kiss and slid my hand under the front of her dress and raised it upwards. I was about three inches from exposing her pussy, only an inch above her thigh high tops, when I felt the wetness on her thighs. I pulled my hand away and licked her sticky juices. She just smiled and walked away. Her pussy juices were even sweeter than her kiss.

After a few minutes, she returned to our booth and I immediately noticed her large breasts were not as high, nor pushed together as much as when she left and her pencil sized nipples were hard and pressing against the thin material of her dress. As she sat down, she opened her purse pulling the bra out enough for me to see.

I smiled at her and said, "Finish your drink and we'll go, that is if you are still up for it."

She took the margarita, turned it up and drained the remaining half! She sat the empty glass down and said, "Oh, I'm so still up for it!"

I paid our check and we walked out of the restaurant holding hands. Since my hotel was directly across the lot, we walked straight there, neither needing to go to a car. Once in the elevator, I pressed 17 and then pressed Melissa against the wall, slipping my tongue into her eager mouth. I then slid my right hand up under her skirt, past the stocking tops and plunged my finger into her soaking wet pussy. She gasped into my mouth as my finger was embedded completely inside her. I could feel that her pussy was shaved smooth, extremely wet and very hot.

I kept finger fucking her until I felt the elevator stop and the doors began to open. We then walked to my room and entered, me behind her. I grabbed her breasts from behind her squeezing them hard, pinching her nipples through the thin dress. She groaned and ground her ample ass into my crotch. I spun her around and kissed her deeply as I reached behind her and unsnapped, then unzipped her dress. I broke the kiss and spread her dress off her shoulders, where it then fell to the floor. She was now naked except for the stockings and her green heels.

"Turn around for me, show me your body," I ordered. She began to turn and strike little posses for me. Her body was great, even with the few extra pounds. She had an incredible hour glass figure, with a nice plump heart shaped ass. I walked over the bed, still fully clothed and sat down on the corner.

"Come over here and lay across my lap," I said.

She walked over and laid herself across my lap, adjusting so that her ass was directly in front of my body, her heavy tits laying on the far side of my slightly parted legs. Once she was comfortable, I reached my left hand under her, inserting my thumb into her pussy, spreading my four fingers over her smooth pubic area. I could flex my fingers and cause her clit to rub against the inside of my palm. I did then several times, working my thumb as far as I could into her pussy. Holding her this way kept her in place even if she squirmed or wiggled. She had her hands flat on the floor to keep her balance.

As I looked at her ass, I realized it was beautiful. Very pale, not a mark, freckle or blemish anywhere. With my left arm between her legs, they were spread just enough for me to see the tight pink hole, puckered and wanting.

"Are you ready for whatever I decide comes next?" I asked, now gently rubbing her ass cheeks with my right hand.

She was moaning lightly and replied, "Oh, yes. Yes, I'm ready for anything."

"I'm going to spank you because you were late at the restaurant, and because I had to tell you twice to take of your panties and twice to take off your bra." I said, my tone soft but stern.

"I understand, I need to be spanked, I was bad," she said.

I then picked up the leather paddle I had purchased earlier and said, "If it gets to bad for you to stand, you say "buttfuck" and I'll stop. I won't stop if you beg me to, or try to get off of my lap. You must yell out 'buttfuck' before I'll stop, " I explained, "do you understand?"

She giggled a little and said, "Yes, I have to say 'buttfuck' to get you to stop spanking me."

I rubbed the thin paddle back and forth over her ass cheeks, she flinched as I caressed the cheeks and slipped between them, crossing over her small pink hole. I then placed it in front of her face and said, "Lick the paddle for me."

She licked it several times and I could see her spit all over one side. After it was nice and wet, I moved it from her tongue and slapped it hard down on first the left cheek, then the right. She lurched and yelped, but she didn't yell out our code word. Her perfect ass now had two perfect red streaks, both about three inches long, two inches wide. I repeated the process of her licking the paddle and then bringing it down hard on her exposed ass for another nine times, so each ass cheek had ten hard swats.

With each swat, she would yelp and cry out. After the tenth swat, her body began to convulse as she had a powerful orgasm against the palm of my hand. Her pussy was gushing fluid out coating my hand and dripping straight down onto the floor.

After her orgasm subsided, I lifter her off my lap, pulling my thumb free of her pussy. She was weak and wobbled slightly on her heels. I stood up and turned her towards me. She had huge tears running down her face and her eyes and facial cheeks were as red as her ass cheeks. I brushed her hair out of her face and leaned in to kiss her. She met me hard, driving her tongue inside my mouth and gave me one of the deepest, most erotic kisses I had ever had.

Breaking the kiss she said, "I've never cum so hard in my life! That was simply amazing!! It hurt, but it hurt so damn good!" She then returned to kissing me.

I broke the kiss next and said, "Now, undress me."

She smiled and grabbed my pullover by the bottom and it was off in seconds. She then asked me to sit on the bed while she removed my shoes, then my socks. She then pulled me up off the bed and unbuttoned my jeans, sliding them down to my knees, then I sat back down and watched her pull them all the way off. My cock was fully erect and had been for some time now, precum leaking from the tip as it was finally freed.

"Melissa, I think it's time you suck me," I said.

She dropped to her knees and slid up between my legs and took my cock into her mouth. She had told me in our previous conversations that she wasn't good at sucking cock and didn't really like it. But she was doing a great job on mine, though she didn't take it very deep, she did use her hands and mouth in unison. I let her suck me for about five minutes before I stopped her.

Lifter her mouth off my cock, I said, "Now, I'll give you a choice. You can let me fuck your throat gagging and all, or you can be tied up and fucked in one of your two other holes."

She didn't even have to think about it, "Oh, I want to be tied up and fucked!" She exclaimed.

I took her to the small round table near the window and her lie down across it, her stocking, high heeled feet on the floor, her large breasts smashed on the table top. In this position, her face was just about cock high, as were her pussy and asshole. I then took each arm and tied it to the leg of the table with the scarves I had purchased. Once her hands were tied tightly, I walked behind her and spread her legs wide, then tied each ankle tightly to the tables' remaining two legs. Her ass cheeks were still very red, and showed some slight bruising from the earlier spanking. With her legs wide open, I could see her cute butthole, pink and inviting and of course her bright pink and red pussy, dripping juices as I stared at it.

I slipped on a condom, cherry flavored and went back around to her face, pulling her hair I lifted her head up, she took my red condom covered cock into her mouth without me having to say a word. She sucked and licked all over the condom then smiled as she let it drop from her mouth.

"MMMM Cherry is my favorite!" She said, taking it back into her mouth.

After a few minutes, I pulled out of her mouth and walked around behind her and slid between her creamy white thighs, my cock only an inch from her pussy. I held onto her hips as I slid my full seven inches into her in one motion.

"AUUGGHHH! YES! YES!" she screamed.

I pushed forward until I was completely embedded in her. I then began to slowly, teasingly withdraw until only the tip of the condom was in contact with her pussy, then I jammed forward again.

"OHHH!! FUCK YES!!!! FUCK ME!!" she was moaning and groaning louder and louder with each thrust into her pussy.

I could feel her heat through the condom and loved how tight her pussy was for a woman of 38. I was pounding into and out of her at a blinding pace, fucking her harder and harder with each thrust. I was staring at her tiny pink butt hole with each thrust, watching it wink at me and I knew that before we were done I would be stretching it much further than it had ever been.

"OH FUUUCCCKKKKK! I'M GOING TO CUM!! I'M CUMMING!!! OH SHSHSHH!" she screamed and her body began to convulse, her pussy squeezing my cock tight and pulsating against me. I continued to pound her dripping pussy as her orgasm carried on and on for several minutes.

As she came down from her orgasm, her pussy released its tight grip on my cock and I knew I was about to cum. I quickly pulled out, pulled the condom off and began to blast my creamy load all over her spanked ass. Shot after shot of my cum landed on her butt, in her crack and on her back. Some was trickling down her crack and mixing with her own juices at the entrance to her pussy.

I walked in front of her, lifter her head again and fed her my deflating cock. She greedily cleaned my cock for me, sucking the remaining cum from me. I then knelt on the floor and kissed her deeply, the taste of my cock still fresh on her lips.

I broke the kiss and smiled, then said, "I'm going to take a shower and I'm going to leave you here, tied up, just like this. But first, I'm going to get you ready for the next session."

"What, can't I get up and shower too? I love hot soapy showers!" She pleaded.

"No, you'll get to shower later. For now, you're my cum soaked slut," I said as I slapped her ass, splashing a wad of my cum and causing her to squeal in pain.

I retrieved the anal lube and the butt plug, then walked back to her. I used my hands to massage my remaining cum all over her ass cheeks and her back. I then used a finger to make sure that most of the cum was cleaned from her crack. This caused moans of pleasure from her.

I spread her cheeks wide and stuck my tongue against the tight hole and began to eat her asshole. She groaned and moaned as my tongue teased her tiny anal bud, licking and stabbing at its hidden opening. I rimmed her ass for five or more minutes, relishing in the taste of how clean and sweet her whole body was. My tongue was now penetrating her and forcing her hole open as she relaxed and fell into the ecstasy of what was happening.

I then stood up and poured a few drops of the anal lube onto her crack, then I lubed the four inch butt plug's tip. I placed the tip at her hole and slowly began to push downward.

"NOOO! I CAN'T TAKE IT! IT FUCKING HURTS!!" she screamed, repeating it over and over as I slowly kept the pressure up and kept pushing forward.

"OH PLEASSSEEEE! STOP!! MY ASS IS SPLITTING OPEN!!" she screamed again.

I never let up and soon, the thick end of the plug popped into her ass and her ass snapped shut around the slender base of the butt plug.

I walked around to her face and knelt again, lifting her head. She had tears streaming down her face and a wild look in her eyes.

"Please, please take it out of me, it really fucking hurts!" she pleaded.

I kissed her and she responded, kissing me deeply her tongue teasing mine. That was when I knew that though in pain, she was sexually thrilled.

As we broke the kiss, she said, "Please? Please take it out of me?" pleading again.

"I'll tell you what, if your pussy is dry and you are not excited, then I'll take it out." I then got up walked behind her and touched the river of girl cum that was running out of her pussy.

I gave the butt plug a thump and said, "I'm hitting the shower, I'll be back in a few." I then walked to the bathroom and took a long hot shower that lasted more than twenty minutes. After I dried off I walked into the main part of the room and saw that she was still tied, wide open, her pussy staring at me and the butt plug still snug in her ass.

When I touched her ass with my fingers, she moaned and said, "I didn't think you were ever coming back, I missed your touch and your mouth and your cock."

I took hold of the butt plug and slowly started to pull it out, getting it almost out then shoving it roughly back in. Fucking her tight asshole with the butt plug, I could tell that there was much less resistance now, meaning that the plug had served its purpose. She was groaning and moaning as I toyed with the plug up her butt until I finally pulled it out completely. Her once tight hole was now open about the size of a nickel.

"OH, I feel so empty, please put it back in, I was just getting use to it!" She sighed.

I stuck two fingers into her pussy, twisting and turning them to get them slippery with her juices, then I slid them into her asshole.

"OHHHH, FUCK!" She yelled, "YES! Fuck me with your fingers!!!"

I fingered her asshole for several minutes with only two fingers, then I worked in a third for several more minutes. I then dropped several drops of the anal lube onto her ass and my fingers and hand slowly worked the fourth finger inside her tight pussy.

"NO! NO! I can't take it anymore! Please!!! MY ASS IS ON FIRE!!!" she screamed.

I continued to plunge my four, cupped fingers in and out of her ass stretching her wider and wider. When I finally pulled them out completely, her asshole gaped open to the size of a quarter.

"You love your ass being fucked don't you?" I asked.

"No!" she replied.

I jammed three fingers in her again and she screamed out and groaned in a deep raspy breath. I fucked her hard with my fingers, slamming them in to the hilt and pulling them back out again.

"Tell me the truth!" I yelled at her.

She was breathing deeply and groaned her reply, "YES! I love my ass being fucked!"