The following takes place 6 months after Part 1
Here I was on an airplane traveling 3000 miles to get tickled into submission and maybe get laid. After my dream night with Judy we said a goodbye and she told me she would be in touch. We exchanged emails every week and I started to phone her. I thought my sister might be upset but she said whatever we wanted to do was cool. We were both adults.
I did miss Judy and I was having a dry spell with the ladies on the East coast. She graciously invited me to her home on the West coast of the United States. I eagerly accepted after she told me she would show me the city and we would get great meals and go to a baseball game. Also. she was going to tickle the shit out of me and have me begging for more. The whole thing had been like a dream. I had thought of this girl a lot after she tickled me as a kid. The tickling and the sex at my sister's house 30 years later was like a dream. Now, I was going to visit her and all our cards were on the table. My sister hinted that she had a strong tickle fetish. She would allow me and encouraged me to go but told me to prepare for an interesting weekend. She said Judy had sent her pictures of her lovely home and one room in particular was different from the others. That was all Ellen told me. I was anticipating a good weekend. Judy was older than I but was in great shape. She was smart and sexy and was a great tickler.
She was a principal but had contacts all over the city. I heard she was well off and sent a driver for me as she said she would be working. The car meandered into a pretty nice and secluded neighborhood. I realized we would be quite alone and wondered if she had anything truly outrageous planned. I had a feeling she was planning on giving me a frightful tickling..
She met me outside and we hugged. She was a 50 year old woman but looked 40. She wore an outfit that I loved on a woman, tight jeans and boots, and a form fitting sweater. We entered the house and began kissing passionately. It took about 30 seconds for her to reach under my shirt and begin tickling me. She pressed forward and continued stroking my cock . I had not had relations since being with her 6 months before in my sister's yard. I was very attracted to her and she really knew how to excite me. We both began getting undressed and she whispered for me to follow her upstairs. We went to the bedroom and had an hour of very satisfying sex. She tickled me when she needed and we ordered Chinese take out. I was tired and drifted into a very peaceful sleep.
I awoke when I felt a soft finger tip tickling the sole of my left foot. "Wake up sleepy head, she laughed". She dove on top of me and started tickling my ribs and sides. I was erect and ready to take her but this time she was in a ticklish mood. 'Tickle, tickle tickle, poor little boy she cooed" and I was really helpless. I knew better but struggled and fell on my stomach on the floor. Predictably, she pounced and tickled me skillfully for a few minutes. She stopped and we watched television and went down for breakfast.
Her house was beautiful and tastefully decorated. At this point she stated that tickling did not have to be on the menu for the balance of the weekend. We could get to know each other and see if there was any potential. I was a little disappointed but said that was fine, She told me to think about it.
A little later I was exploring her place some more. Judy had gone out to a meeting , looking sensational in a form fitting dress. I was lucky to be spending the weekend with a hot, smart woman. I kept poking around and found a door on the other end that was marked private. The sign also said "THOSE WHO ENTER HAVE A 4 HOUR LIMIT" I had a feeling that was down there would lead to a little trouble. I knew Judy was capable of a lot more in tickling. She just loved to do it and had a gleam in her eye when she did it. I knew what was down there and I wanted to go. I also knew it would be a difficult 4 hours if it happened.
When Judy returned I immediately asked her about the sign on the door and what was down there. '"You can guess, she said" But I thought we would just have a nice weekend, have sex, go out to restaurants, and see if we really like each other" However, she cooed, if you want to trade that for door number one, you can do that" But I promise you you will be there for 4 hours . That is a guarantee. Unless you want to stay for more. But I think after 4 hours you will have had enough. I noticed she had really nice purple nail polish on her well manicured nails. I said. 'Judy. is that where you do serious tickling" She said, "You can find out. but again there is a 4 hour stay. I am not daring you. Frankly, you are a really ticklish guy and you are probably better off skipping it. Another smile sent chills down my spine. 'You do not have to decide right now. Lets go upstairs. I followed her upstairs admiring her sexy ass as always. She showed me her art collection from the orient. Unfortunately, I could only think what would befall me if I went down stairs. I
knew I may be biting off more than i could chew.
It was already Saturday afternoon. I knew that I could not resist the basement. I wanted to get it over with. "Judy, I am ready to go to the basement" I stated. Her look changed somewhat and she simply stated "I have been tickling you for fun" Downstairs, its a little more intense. A lot more frankly. I will not stop if you beg and cry. Do you want that" I really should have said no. But I came all this for for an adventure and I was determined. Judy said. 'As soon as you are downstairs you have crossed the Rubicon. Believe me, there is no choice left. Please think about it. "I told her I was ready. At 3 Pm Saturday I entered the basement.
I was really turned on. As I suspected there was a bondage device like a cross where you are strapped in and hands and feet are completely immobile. There was a basic padded stock bench where feet are put through and hands are fastened as comfortably as possible in front. A few other things which I didn't want to know about were there. Judy said, its better to volunteer than be called" I told her that I may try and run away. She said, that would lengthen the stay to 6 hours. She smiled. 'I will not hurt you permanently but you will have an interesting experience. She then began by flipping me to the ground and diving on me . She skillfully tickled my sides. my pits, and every exposed piece of skin she could find. 'She said, you are going to the stocks". I got up and walked over. That is why I was down there. To see if i could stand up to her best.
Judy fastened me in. My hands were comfortably secured in front and my feet were pulled through the holes on either side. Judy then put a small gag in my mouth. I did not fight her. It was over. She said my time had started and she would be right back. She closed the lights as she left and was there to ponder my situation. I was in shorts and tea shirt in a basement with a girlfriend who was going to tickle torture me for 4 hours. But it was my doing.
Judy returned in a black skin tight leather suit.Naturally. Par for the course. She looked amazing. She removed my gag. She had a mask covering her eyes. She showed me her nails which somehow seemed longer. I tried to be funny and asked if I needed to call her mistress Judy. She said that would be fine.I suddenly got a real bad feeling. 'I want out Judy." She slapped me, not too hard and told me it was mistress. She said 'no mercy
now." You will do the 4 hours, you can stand it. You want it. You are a submissive" Admit it and go with it" I really did like strong woman, and I could always plead for mercy. 'Tickle, Tickle little boy",she said softly. Tickle, tickle little boy" I tried to move but realized there was absolutely no way to do that. Judy showed me her nails and began. She skillfully scraped three of them from my toes down to my heal on my right foot. 'Tickle, tickle little boy" she cooed. The feeling was electric and torturous. Judy, no this is a mistake. please. " Judy smiled and said "I like begging" Are you going to humiliate yourself and do that for 4 hours. Or I can just tickle you and then we will have sex you will never forget." I tried to breath easy and hoped the sensations would get better. She skillfully used all 10 nails on my feet and I went ballistic. "Do I have to gag you, asked my mistress. I told her not to. that it was an awful feeling. "Be a grown man and take it or I will make it worse." I realized that I really screwed up. This was a way to lose a tickle fetish, that was for sure. Judy then bent down and nibbled my toes. She did it with enough force to really excite me, and it was an incredible feeling. I was dealing with an expert. She then rubbed oil into my feet and looked at me and smiled. 'Judy, no. you don't have to do this" 'I do, little boy. you will have something to think about for the next 30 years. She rubbed the oil in and slowly began just circling my feet with her soft fingers. I was hoping I would faint because the sensation were hard to take..Again I tried to take deep breaths to make it better. Unbelievably, I was excited and real hard. Judy nibbled my toes again and the sensations were beyond what I ever experienced. A pro was a pro. I was dying. "Time for a rest, she said softly. close your eyes and relax. Normally I do not give rest."
She gave me 10 minutes and moved to my underarms. Skillfully, she came behind me and gently used her nails . Slowly digging them into my pits. I was hoping it would hurt but again the ticklish sensations were too much. 'Judy, stop, spank me instead, I can't take it" , I blurted out. '"Don't worry little boy,that will happen, I promise; . Judy continued that tactic for about 10 minutes and than went back to my feet. "How about some tic tack toe' she laughed. If you win, I will cut down the torture time, no strings attached. " She secured a sharp pen and told me I would go first. She drew the lines and we played. I had no chance. I also knew she would take warm water and a washcloth and scrub my feet clean. I was so hard I wanted to burst. 'Again?, she asked. This time if you lose I will add an hour to your time. If you win, I will stop and let you go. I could not take that chance. "No more games". I said. You will be in trouble when I get out of here." I didn't really know where the bravado came from. She laughed and said, 'you will be lucky to be able to get up the steps when you get out..,"She gagged me and began a another ticklish attack on my feet just spider tickling both of them. 15 minutes later she stopped and removed my gag. I was pretty much toast. She lifted up my head and slapped me,again to show me who the boss was. . This was unbelievable. I was getting the full experience.
Judy helped me out of the stocks and pushed me to the cross on the wall. She strapped me in and cut my tea shirt and pulled down my shorts and briefs.
She showed me a white feather and tickled my balls, cock and nipples alternately for about 20 minutes. I really wanted to cum. "'if you cum, do you know how ticklish you will be" I did. An orgasm increases sensitivity by a lot. . I didn't care. Judy said she would think about it and tickled my nose with the feather and back down to my nipples. I pleaded for sexual release.She laughed and slowly began jerking me off. The explosion was pretty intense. "You need a break, that's for sure" 'But you are staying the whole 4 hours" Its the Hotel California, you can check out any time you like, but you can never leave" I loved the song reference but needed rest. I fell asleep. and do not know how long I was out.
I woke up back in the stock contraption and Judy decided to play this little piggie on my toes. ' I couldn't help it. I told her I would do anything for her to stop. 'I am keeping you here the rest of the weekend, so shut up. She slapped my face , a bit harder than before and it stung. I hated her and I loved her for the way she was treating me. . Then she said, If you can perform simple oral sex and make me climax, I will release you. You have 10 minutes. If you can't make me cum, I will come back to the east coast in 3 weeks and put you through a lot worse than this. 'Challenge accepted' I said with as much energy as I had left. She stripped for action and my energy returned. Fortunately, I am good at what she asked for or she really craved oral sex. Who knows?. I tried hard and she had a thundering climax. My jaw hurt and she laughed and said 'How about another." "Can I just go upstairs and sleep for awhile and then later, for sure." She agreed. The time in the basement was only about 2 hours and I knew I owed her more service. This was the perfect woman in my view. She was right.I needed her to help me out of the basement.
I collapsed in her bed and she snuggled up next to me. '"You owe me 2 more hours in the basement before you leave, sport and they will be worse". So rest up.Your lucky I really like you. I fell asleep smiling at my good
fortune. Absolutely the perfect woman.
part 3 to come
Here I was on an airplane traveling 3000 miles to get tickled into submission and maybe get laid. After my dream night with Judy we said a goodbye and she told me she would be in touch. We exchanged emails every week and I started to phone her. I thought my sister might be upset but she said whatever we wanted to do was cool. We were both adults.
I did miss Judy and I was having a dry spell with the ladies on the East coast. She graciously invited me to her home on the West coast of the United States. I eagerly accepted after she told me she would show me the city and we would get great meals and go to a baseball game. Also. she was going to tickle the shit out of me and have me begging for more. The whole thing had been like a dream. I had thought of this girl a lot after she tickled me as a kid. The tickling and the sex at my sister's house 30 years later was like a dream. Now, I was going to visit her and all our cards were on the table. My sister hinted that she had a strong tickle fetish. She would allow me and encouraged me to go but told me to prepare for an interesting weekend. She said Judy had sent her pictures of her lovely home and one room in particular was different from the others. That was all Ellen told me. I was anticipating a good weekend. Judy was older than I but was in great shape. She was smart and sexy and was a great tickler.
She was a principal but had contacts all over the city. I heard she was well off and sent a driver for me as she said she would be working. The car meandered into a pretty nice and secluded neighborhood. I realized we would be quite alone and wondered if she had anything truly outrageous planned. I had a feeling she was planning on giving me a frightful tickling..
She met me outside and we hugged. She was a 50 year old woman but looked 40. She wore an outfit that I loved on a woman, tight jeans and boots, and a form fitting sweater. We entered the house and began kissing passionately. It took about 30 seconds for her to reach under my shirt and begin tickling me. She pressed forward and continued stroking my cock . I had not had relations since being with her 6 months before in my sister's yard. I was very attracted to her and she really knew how to excite me. We both began getting undressed and she whispered for me to follow her upstairs. We went to the bedroom and had an hour of very satisfying sex. She tickled me when she needed and we ordered Chinese take out. I was tired and drifted into a very peaceful sleep.
I awoke when I felt a soft finger tip tickling the sole of my left foot. "Wake up sleepy head, she laughed". She dove on top of me and started tickling my ribs and sides. I was erect and ready to take her but this time she was in a ticklish mood. 'Tickle, tickle tickle, poor little boy she cooed" and I was really helpless. I knew better but struggled and fell on my stomach on the floor. Predictably, she pounced and tickled me skillfully for a few minutes. She stopped and we watched television and went down for breakfast.
Her house was beautiful and tastefully decorated. At this point she stated that tickling did not have to be on the menu for the balance of the weekend. We could get to know each other and see if there was any potential. I was a little disappointed but said that was fine, She told me to think about it.
A little later I was exploring her place some more. Judy had gone out to a meeting , looking sensational in a form fitting dress. I was lucky to be spending the weekend with a hot, smart woman. I kept poking around and found a door on the other end that was marked private. The sign also said "THOSE WHO ENTER HAVE A 4 HOUR LIMIT" I had a feeling that was down there would lead to a little trouble. I knew Judy was capable of a lot more in tickling. She just loved to do it and had a gleam in her eye when she did it. I knew what was down there and I wanted to go. I also knew it would be a difficult 4 hours if it happened.
When Judy returned I immediately asked her about the sign on the door and what was down there. '"You can guess, she said" But I thought we would just have a nice weekend, have sex, go out to restaurants, and see if we really like each other" However, she cooed, if you want to trade that for door number one, you can do that" But I promise you you will be there for 4 hours . That is a guarantee. Unless you want to stay for more. But I think after 4 hours you will have had enough. I noticed she had really nice purple nail polish on her well manicured nails. I said. 'Judy. is that where you do serious tickling" She said, "You can find out. but again there is a 4 hour stay. I am not daring you. Frankly, you are a really ticklish guy and you are probably better off skipping it. Another smile sent chills down my spine. 'You do not have to decide right now. Lets go upstairs. I followed her upstairs admiring her sexy ass as always. She showed me her art collection from the orient. Unfortunately, I could only think what would befall me if I went down stairs. I
knew I may be biting off more than i could chew.
It was already Saturday afternoon. I knew that I could not resist the basement. I wanted to get it over with. "Judy, I am ready to go to the basement" I stated. Her look changed somewhat and she simply stated "I have been tickling you for fun" Downstairs, its a little more intense. A lot more frankly. I will not stop if you beg and cry. Do you want that" I really should have said no. But I came all this for for an adventure and I was determined. Judy said. 'As soon as you are downstairs you have crossed the Rubicon. Believe me, there is no choice left. Please think about it. "I told her I was ready. At 3 Pm Saturday I entered the basement.
I was really turned on. As I suspected there was a bondage device like a cross where you are strapped in and hands and feet are completely immobile. There was a basic padded stock bench where feet are put through and hands are fastened as comfortably as possible in front. A few other things which I didn't want to know about were there. Judy said, its better to volunteer than be called" I told her that I may try and run away. She said, that would lengthen the stay to 6 hours. She smiled. 'I will not hurt you permanently but you will have an interesting experience. She then began by flipping me to the ground and diving on me . She skillfully tickled my sides. my pits, and every exposed piece of skin she could find. 'She said, you are going to the stocks". I got up and walked over. That is why I was down there. To see if i could stand up to her best.
Judy fastened me in. My hands were comfortably secured in front and my feet were pulled through the holes on either side. Judy then put a small gag in my mouth. I did not fight her. It was over. She said my time had started and she would be right back. She closed the lights as she left and was there to ponder my situation. I was in shorts and tea shirt in a basement with a girlfriend who was going to tickle torture me for 4 hours. But it was my doing.
Judy returned in a black skin tight leather suit.Naturally. Par for the course. She looked amazing. She removed my gag. She had a mask covering her eyes. She showed me her nails which somehow seemed longer. I tried to be funny and asked if I needed to call her mistress Judy. She said that would be fine.I suddenly got a real bad feeling. 'I want out Judy." She slapped me, not too hard and told me it was mistress. She said 'no mercy
now." You will do the 4 hours, you can stand it. You want it. You are a submissive" Admit it and go with it" I really did like strong woman, and I could always plead for mercy. 'Tickle, Tickle little boy",she said softly. Tickle, tickle little boy" I tried to move but realized there was absolutely no way to do that. Judy showed me her nails and began. She skillfully scraped three of them from my toes down to my heal on my right foot. 'Tickle, tickle little boy" she cooed. The feeling was electric and torturous. Judy, no this is a mistake. please. " Judy smiled and said "I like begging" Are you going to humiliate yourself and do that for 4 hours. Or I can just tickle you and then we will have sex you will never forget." I tried to breath easy and hoped the sensations would get better. She skillfully used all 10 nails on my feet and I went ballistic. "Do I have to gag you, asked my mistress. I told her not to. that it was an awful feeling. "Be a grown man and take it or I will make it worse." I realized that I really screwed up. This was a way to lose a tickle fetish, that was for sure. Judy then bent down and nibbled my toes. She did it with enough force to really excite me, and it was an incredible feeling. I was dealing with an expert. She then rubbed oil into my feet and looked at me and smiled. 'Judy, no. you don't have to do this" 'I do, little boy. you will have something to think about for the next 30 years. She rubbed the oil in and slowly began just circling my feet with her soft fingers. I was hoping I would faint because the sensation were hard to take..Again I tried to take deep breaths to make it better. Unbelievably, I was excited and real hard. Judy nibbled my toes again and the sensations were beyond what I ever experienced. A pro was a pro. I was dying. "Time for a rest, she said softly. close your eyes and relax. Normally I do not give rest."
She gave me 10 minutes and moved to my underarms. Skillfully, she came behind me and gently used her nails . Slowly digging them into my pits. I was hoping it would hurt but again the ticklish sensations were too much. 'Judy, stop, spank me instead, I can't take it" , I blurted out. '"Don't worry little boy,that will happen, I promise; . Judy continued that tactic for about 10 minutes and than went back to my feet. "How about some tic tack toe' she laughed. If you win, I will cut down the torture time, no strings attached. " She secured a sharp pen and told me I would go first. She drew the lines and we played. I had no chance. I also knew she would take warm water and a washcloth and scrub my feet clean. I was so hard I wanted to burst. 'Again?, she asked. This time if you lose I will add an hour to your time. If you win, I will stop and let you go. I could not take that chance. "No more games". I said. You will be in trouble when I get out of here." I didn't really know where the bravado came from. She laughed and said, 'you will be lucky to be able to get up the steps when you get out..,"She gagged me and began a another ticklish attack on my feet just spider tickling both of them. 15 minutes later she stopped and removed my gag. I was pretty much toast. She lifted up my head and slapped me,again to show me who the boss was. . This was unbelievable. I was getting the full experience.
Judy helped me out of the stocks and pushed me to the cross on the wall. She strapped me in and cut my tea shirt and pulled down my shorts and briefs.
She showed me a white feather and tickled my balls, cock and nipples alternately for about 20 minutes. I really wanted to cum. "'if you cum, do you know how ticklish you will be" I did. An orgasm increases sensitivity by a lot. . I didn't care. Judy said she would think about it and tickled my nose with the feather and back down to my nipples. I pleaded for sexual release.She laughed and slowly began jerking me off. The explosion was pretty intense. "You need a break, that's for sure" 'But you are staying the whole 4 hours" Its the Hotel California, you can check out any time you like, but you can never leave" I loved the song reference but needed rest. I fell asleep. and do not know how long I was out.
I woke up back in the stock contraption and Judy decided to play this little piggie on my toes. ' I couldn't help it. I told her I would do anything for her to stop. 'I am keeping you here the rest of the weekend, so shut up. She slapped my face , a bit harder than before and it stung. I hated her and I loved her for the way she was treating me. . Then she said, If you can perform simple oral sex and make me climax, I will release you. You have 10 minutes. If you can't make me cum, I will come back to the east coast in 3 weeks and put you through a lot worse than this. 'Challenge accepted' I said with as much energy as I had left. She stripped for action and my energy returned. Fortunately, I am good at what she asked for or she really craved oral sex. Who knows?. I tried hard and she had a thundering climax. My jaw hurt and she laughed and said 'How about another." "Can I just go upstairs and sleep for awhile and then later, for sure." She agreed. The time in the basement was only about 2 hours and I knew I owed her more service. This was the perfect woman in my view. She was right.I needed her to help me out of the basement.
I collapsed in her bed and she snuggled up next to me. '"You owe me 2 more hours in the basement before you leave, sport and they will be worse". So rest up.Your lucky I really like you. I fell asleep smiling at my good
fortune. Absolutely the perfect woman.
part 3 to come
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