Best Business Trip Ever?

I've been reading Literotica stories for years but never written one of my own. I have dyslexia, which impacts my ability to spell. As a child and young adult I didn't write well because fear of misspelling disrupted my flow of thought. Thank goodness for spellcheck! I can now write my stream of consciousness without worry!

This story is purely fiction. It memorializes a fantasy that has been rattling around in my brain for a number of years. I hope you enjoy it and would love to see feedback from readers.

I was at the start of a business trip a few months ago sitting at my gate in the Seattle Airport waiting to board a flight to Los Angeles. I am a real estate developer so I was heading to Los Angeles for a four days to look at potential development opportunities. It was early morning and the airport was less busy than normal. There was an attractive young lady sitting across from me in a heated telephone conversation. I have no idea what she was talking about but she seemed angry and she was quite animated. For some reason, to me, this made her even more attractive and I felt the start of a little stirring down below. She appeared to be in her late 20's or possibly early 30's. Far too young for me, I'm in my early 60's, but a boy can dream! She was a brunette with straight shoulder length hair and a thin, perfectly proportioned face. She had lovely brown eyes, a petite nose and luscious thick lips. She got up and started pacing in the area of her seat as she finished her call so I could see she was tall and thin, maybe 5 foot 8 inches and in the 120 pound range. She was wearing tight yoga pants so I could tell she had a very nice figure. Her ass looked deliciously toned and the way the pant material crawled up her private parts took my breath away. Unfortunately she had on a tight sweatshirt so i couldn't tell what was going on up top.

A little about me before I go on. I am a 62 year old real estate developer. I am just shy of 6 feet all and weigh around 170 pounds. My hair has turned salt and pepper over the years but, at least I have all of it. After my divorce a few years back I started a regular exercise routine so I stay relatively fit. I also eat a healthy diet so I don't have the extra pounds many men my age seem to carry. I have been told I am somewhat attractive but I have never thought much of my looks.

The young woman finished her call, looked straight at me and said harshly "what the fuck are you looking at?". I was a little shocked, taken back and stumbled over my words as I tried to respond. I, I, I'm sorry. Y, y, you just look really nice this morning. She said, apparently I'm not that nice, my boyfriend just broke-up with me because, in his words, I'm a fucking bitch. I apologized for staring at her and told her that any guy that would break up with her is a moron. She laughed and thanked me for the compliment. She also apologized for being rough on me at first. We continued talking until boarding. The conversation flowed easily and we seemed to form a connection. Her name was Karin and lived and worked in Los Angeles. Karin was in Seattle visiting her long distance boyfriend, now ex-boyfriend. She owned her own home, enjoyed being in Los Angeles, and wanted to stay there long-term.

Unfortunately a first class boarding announcement came over the loudspeaker. I said, that's me, and ended the conversation. I told her to it was nice talking to her and wished her well.

I was sitting in my first class aisle seat while other passengers were boarding and walking by me to their seats. As I was waiting for everyone else to be seated I was kicking myself for not asking for her number. I mean, there is a significant age difference so I really didn't think she would go out with me. But if you don't ask you don't get. So I couldn't shake feeling like an idiot. As I was beating myself up, I saw Karin starting to walk down the aisle. As she approached my seat the man in the seat across the isle from me stood up to put something in the overhead bin. Karin turned her body so she faced me and squeezed by. As she passed me her tits brushed against the top of my head. I looked up at her and she looked straight at me with a very wicked smile.

I couldn't stop thinking about that smile, and those tits, for the entire flight. I didn't know what the smile meant and started fantasizing about all the things I wanted to do to her. I may be in my 60's but my dick still works. I think I was hard for the entire flight. I had to fold my jacket and keep it in my lap to make sure no one noticed my hard-on.

After exiting the plane, I waited around to see if I could get a glimpse of her as she exited. Just my luck, she walked through the doorway, looked straight at me, and gave me a wonderfully warm smile. In that moment I melted and felt like I might be willing to do anything for this girl.

She walked up to me and said, "hi again". We talked for a minute and then she said she was meeting a friend for an early dinner but asked if I would like to come to her place for a nightcap at around 8:00pm. My head was spinning. I couldn't believe this vision, my dream girl, just asked me over for what seemed like booty call!

I somehow contained my excitement and left the airport in a rental car to see a few potential development sights. When I finally finished the property visits I made my way to my hotel. By the time I got to my hotel I was shaking with anticipation. I decided to order room service for dinner and then showered, shaved, and did some personal grooming to get ready for who knows what!

I pulled up to her house just before 8:00pm. I hade no idea what to expect but I had very high hopes. I rang her bell at 8:00 sharp. When she opened the door my heart skipped a beat and I lost my breath for a moment. Karin was wearing a tight white top that left her belly exposed. She wasn't wearing a bra so I would see her nipples through the thin material. Her nipples appeared to be pierced and I could see the rings as well. She was also wearing yoga pants similar to the ones she wore earlier in the day. She greeted me with a warm embrace and I thought I died and gone to heaven.

She invited me in and told

me to have a seat on the couch in her den. She disappeared into the kitchen and returned with what appeared to be two glasses of whiskey on the rocks. She laughed and said she hoped it was okay because it's all she had. I told her it was perfect and we started in on some more conversation.

For some reason I was a little nervous and didn't make a move. Maybe it was the age difference, maybe it was something else, I can't explain it. In any case she finally leaned in and we had a nice deep kiss. She then very bluntly said "You know why you're here, right?" I said I assumed it was a booty call? She laughed and said "Yes, exactly."

Karin then said she had gone to LA to visit her boyfriend but all they did was fight and they never got around to having sex. It left her kind of horny. I told her I was sorry she broke up with her boyfriend but I was glad to be lucky enough to accommodate her needs. She then gave me a side eye sort of look and said she sometimes liked to play a little sex game when she could find a willing partner. I asked her what she had in mind and she said "It's really very simple. You aren't allowed to cum unless I give you permission and you need to earn my permission by following my instructions." I didn't know what I was getting myself into but I told her I was willing to give it a try. She said before I said yes I needed to know that if I did not follow her instructions or I came without permission I would be punished. I asked what kind of punishment and, with a very wicked look, said there were too many options to mention. But she did promise me she wouldn't cause any permanent damage and said I could have a safe word in case things got too intense. That sounded reasonable so I told her I was in. Karin then gave me one last warning by saying if I used my safe word she would stop what she was doing and tell me to leave. In essence, I wouldn't get to fuck her. I gave it some thought for a couple of seconds and then told her I was still in. She told me I should use the word "bitch" as my safe word and then instructed me to take off all of my close, fold them neatly on her couch, and kneel on the carpet facing the hallway leading to her bedroom.

I did as instructed and waited full of anticipation, along with a tinge of anxiety, for several minutes. When Karin returned I nearly lost it. She was wearing a corset that didn't really cover much of her breasts. Her breasts were beautiful, not large but spectacular with perky pierced nipples and aureolas a bit larger than a quarter. She also had on stockings and a guarder that left a perfectly hairless pussy exposed for me to see. I said "Wow, you look incredible!" She knelt down and got very close to me. She reached forward and gently grabbed my balls in her right hand while she brought her face just a few inches from mine. While looking me in the eyes very intensely she gave my balls a light squeeze while she said "thank you." She proceeded to squeeze a little harder and told me that from here on out I was to not speak unless I was spoken to and I should call her Mistress Karin. She then squeezed significantly harder and said "do you understand?" I gasped from the pain and somehow blurted out "Yes Mistress Karin." She said "good boy" and let go of my balls.

She then attached a collar to my neck, a leash to the collar, and instructed me to follow her on my hands and knees to her bedroom. I did as instructed and once in the bedroom I saw a nice queen size bed with night stands, a dresser, a full length mirror on one of the walls, a chair in one of the corners and a closet. It was roomy with a good amount of floor space aside from the furniture. Karin then informed that we were going to spend some time testing my skills. She then pulled on the leash and told me to stand. She left the collar on but proceeded to take off the leash. She laid down on her bed and told me to demonstrate how skilled I was at licking and sucking tits. I mouth was watering, my cock was rock hard, and I could wait to get my mouth on those beautiful tits.

I climbed on the bed and went straight for one of her nipples. I sucked the nipple and played with the piercing with my tongue for about 30 seconds when she interrupted my bliss and said "stop! You're not very good at this. Let me demonstrate." She then sat up, leaned forward and started licking my right breast. She didn't lick or suck the nipple at first but she did kiss and lick just about every other part. It was driving me crazy. My cock wanted to explode. Finally she took my nipple into her mouth and sucked it while playing with it with her tongue at the same time. In that moment I wanted to throw her on the bed and fuck her brains out but I exercised self control because I wanted to see what would happen the rest of the evening.

She ultimately stopped and instructed me to give it another try. Karin told me to do to her exactly what she had done to me. I proceeded to lick, kiss, and suck every inch of both of her tits. While I was doing so I sensed her excitement as her breathing speed up. After about 10 minutes she told me to stop. She looked at me and told me I was a fast learner. I very proudly said "Thank you Mistress Karin." She gave me a stern look and said although I was a fast learner my skills still needed improvement so she needed to punish me as encouragement to improve my skills in the future.

I didn't know what to think. I thought I had done a pretty good job but I was still going to be punished. I felt my stress levels rise as I waited for whatever was coming next. Mistress Karin instructed me to get on the floor on my hands and knees. She instructed me to lean my weight forward on my forearms. While I was positioning myself I saw her walk to the dresser and take a large wooden paddle out of the top drawer. The paddle had holes in it for some reason and looked intimidating. For me that was an "oh shit" moment. I had never been spanked and didn't know what to expect. Mistress Karin told me my punishment would be 10 smacks with the paddle. She told me each smack would be harder than the last and the last few may be very unpleasant for me. I don't know why but my cock was still rock hard. She asking if I was ready and I reluctantly said yes Mistress Karin.

She proceeded to tap my ass cheeks lightly with the paddle and then drew back and gave me the first wack. I thought to myself that it wasn't so bad but the next wack was harder and, as she warned, they continued getting harder as she went along. The last three were so hard they brought tears to my eyes. It really hurt and I was breathing heavily trying to hold back the tears. All the while my cock never softened. It was still hard as a rock and dripping pre-cum. She rubbed my ass cheeks and told me my next test was pussy eating skills and asked if I was ready. My ass was still stinging but the thought of licking this gorgeous woman's hairless pussy was too much. I said "Yes Mistress Karin, I'm ready."

Mistress Karin walked over to her bed, sat on the edge, leaned back on her elbows and spread her legs. In a stern voice she said "now crawl over here and get started."

I began by running my tongue up and down the outer lips of her pussy alternating sides. The smell was intoxicating. She was already nice and wet and her taste was delightful. After a couple of minutes she started breathing harder. At that point I moved my tongue to her clit and pressed into it firmly. She grabbed the back of my head and pulled my face into her so my tongue was pressing against her clit even harder. I started rubbing her clit with my tongue while I was firmly pressed into her. In no time she was bucking her hips and I could feel her body tense. She stopped breathing as she climaxed and squirted all over my face.

I don't recall ever making a woman squirt before and I was excited beyond belief. My cock was rock hard and, as hard as it used to get when I was a teenager.

Mistress Karin thanked me for the orgasm and instructed me to lay face-up on the bed. She then proceeded to secure me, spread eagle to the bed frame, with cuffs she already had in place. After I was secured she crawled up next to me and grabbed my balls again. She gave them a very firm squeeze and reminded me I was not allowed to cum otherwise there would be consequences. I thought about the padding I already received and was intent on avoiding further punishment.

Mistress Karin let go of my balls, leaned forward, and started licking my balls very gently. Not enough friction to make me cum but enough to give me immense pleasure. I started squirming in order to increase the friction and she promptly stopped licking. She told me to lay still or she would send me home and I told her I would do my best. She proceeded to give me the most incredible blow job I had ever had. But she knew exactly when to stop in order to prevent me from climaxing. My head was spinning I wanted to cum so bad.

Mistress Karin stopped the blow job, got off the bed, and told me she would be back in a few minutes. I was still secured to her bed and alone in her room. My cock was so hard! I wanted to fuck her and blow my load so badly!

She must have been gone for 15 minutes or more. When she returned my cock was still hard but starting to wilt a bit. She surprised me by putting a large plastic bag filled with ice water on my cock. I was startled and said "What the fuck!".= She slapped my face hard and told me not to talk to her that way. She said she needed me soft for the next step in my training.

I had experimented with chastity devices on my own a few years prior so I had an idea of what was coming next. But she had already teased and denied me quite a lot so I was confused as to where this was leading.

Sure enough, after I was soft Mistress Karin secured a chastity device to my cock. She then left the room for a few minutes. I was still secured to the bed so I couldn't go anywhere. My head was racing. I was trying to figure out where this was leading.

When Mistress Karin returned she told me I was to follow her instructions if I ever wanted to get let out of chastity. She untied me and let me have a look at her handy work. The cage seemed very secure. There didn't seem to be a way to get it off without the key, or without injuring myself. She said it was getting late so she wanted me to leave and come back the next evening at 8pm. I panicked! I was still so worked up I couldn't imagine keeping the cage on until the next night. I teared up as I dropped to my knees and begged her to let me out. She said she might consider letting me out if I would do something for her. I said yes, yes, of course, anything.

Mistress Karin the dropped to her knees and bent forward leaning on her elbows. Her beautiful ass was sticking into the air and for the first time I could see it as as hairless and smooth as her pussy. She said "Lick my asshole while I think about how you might earn your way out of chastity."

While I had never licked an ass hole before I really wanted out so I proceeded to lick in circles around her hole. She seemed to like it as I could tell she was short of breath when she ordered me to stick my tongue in her hole. My mind was all over the place as I hesitated while wondering how I was going to get out of this predicament. Unfortunately my hesitation made her lose her temper. She yelled "Stick your tongue in if you ever want out!"

Without thinking I plunged my tongue into her hole and began fucking her with it. She started bucking her hips in rhythm with my tongues motion and ultimately had another earth shattering orgasm.

After she calmed down she got up, went to her dresser drawer, and pulled out what looked to be a 6 or 7 inch realistic looking dildo. She handed it to me as told me she wanted me to take it back to my hotel room and spend the rest of the night practicing sucking it and deep throating. She said if I could demonstrate good cock sucking technique the next evening she would let me out of the cage and let me cum. I was speechless. I had never even fantasized about sucking a cock or dildo. And now she wanted me to practice and demonstrate technique? I didn't know what to say or do.

Mistress Karin walked me out to the living room and told me to get dressed and leave. She reminded me about the condition of my release and said she couldn't wait to see my demonstration.

I got dressed, grabbed the dildo, and left without saying a word.