A Virgin Locked In Chastity

I was 18 when I moved in with Ruth. Ruth was my new land lady, I moved in with her for my university studies time frame. She had a big house and leased a room.

Ruth was 56, in great shape, she was about 170 cm tall and about 50 kg with small breasts and a very nice figure.

I was very excited to move, I loved the idea of sharing a house with a woman. I imagined myself peeking into the shower or her room to see her naked or taking her panties from the laundry basket for masturbating. All those thoughts got me very aroused, my cock was hard as I arranged my stuff in the room.

I had not cum in two weeks. My parents were always around in the last two weeks so I could not jerk off, but now, I have my own room, I am so horny, I can finally jerk off.

I opened my lap top, looked for a Jerk Off Instructions clip, got naked and started jerking off. The girl in the clip was so hot. She touched herself, made jerking moves on a virtual cock, it was so sexy. After about 10 minutes I exploded, the cum burst out and landed on my chest and belly.

Ruth entered my room the moment I came, she just opened the door wide just as I shot my cum, she saw everything. Her reaction was furious...

"Young man, what is this? Are you watching porn and jerking off in my house?" She demanded. "This is a behavior I can not allow, I will need to make sure it never happens again!"

She left the door open and went away to her room.

I was so scared and so aroused, my hard-on would not go away. She returned 5 minutes later and saw me.

"Still hard?" She questioned. "This is not good. Jerk it off and get it soft. Do it now young man, we have no time."

I was so embarrassed and surprised, I could not get soft. I was naked in the same room with a very sexy and very strong woman. I was aroused like I'd never been in my life.

"What are you waiting for? Jerk it off, get it soft!" She ordered, impatient.

I obeyed her instantly. I started to stroke myself in front of her, her firm gaze assessing my every move, watching me. It took me 5 minutes to cum again, but I still wasn't soft. I needed to keep going and cum a third time to complete the task I'd been given.

Once I was finally soft, she pulled out a metal chastity cage. Ruth came close to me, she lubed my cock and balls with the lotion I'd been using to jerk off, this was the first time a woman ever touched my cock and balls. I was getting hard again, but she was fast enough to cage me before my cock could stiffen. And there it was, I was locked in a chastity cage.

The next month was very difficult. Ruth completely ignored the incident, nothing was said. We just behaved as if all was normal. As if nothing had happened. Not a single word about jerking, sex, getting caught or chastity. I had never been this horny in my life, and so helpless. I could not get hard, could not jerk off and definitely could not cum, my balls were so full and so sensitive.

Then, one Saturday morning, at 10 AM Ruth called me into her bedroom. She was wearing tight jeans and a white tight T-shirt, she looked very sexy.

"Strip." She ordered.

I stared for a moment, still shocked that she'd acknowledged me at all.

"Get naked." She snapped, more forceful this time. "Sit on the armchair."

I obeyed immediately.

She told me to put my hands behind the chair and not move them and to put my legs apart on the arms of the chair. It was like sitting in a gynecologist chair. She took the key out and unlocked my cock. I got hard immediately. She started jerking me, but did not touch my cock head, only the shaft. She made sure I would not cum right away, it was obvious she was very experienced. My hips could not stop moving. I was so eager to cum, I started moaning. She kept me right on the edge of cumming.

Then she stopped.

"You need to make a choice." She said. "You can get a full satisfying orgasm from my hands. I will make you cum like you never have in your life. But then you will need to be locked for 3 months... I could give you a ruined orgasm. All that stored cum will be freed. But there will be no sexual satisfaction in this orgasm and you will be locked for another month... Or you can get the full orgasm like in the first option but you must eat all the cum that you ejaculate. Every drop of it. You will then get to cum again after one week. But you need to keep in mind that if you take the third option it means that you agree to eat your cum every time you cum from now on. No way out of this agreement."

I wasn't able to think, all I wanted to do was explode. I just moaned and fucked the air with my hips so she made the choice for me. I got my first ruined orgasm. It was so frustrating, I felt no pleasure, the cum just burst out and I felt nothing. I started crying and begging Ruth to let me cum, she just sat there waiting for me to get soft and locked me back up.

The following month was hell for me. I was horny and frustrated, I cried a lot. I knew what was going to happen when she called me to her room again.

The month passed and the moment I feared arrived.

I was on the chair in her room, in the gynecologist position just like in the previous month. Ruth took the chastity cage off and very gently masturbated me. She massaged my balls, worked my shaft, teasing me to the point that my moans were almost screams. Then came the three choice question.

"Let me cum, please!" I begged, crying.

"Are you sure?" Ruth asked firmly. "It means three months in chastity without relief."

All I wanted was to cum, I could not take it anymore.

Ruth stopped jerking She let me calm down a bit, she wanted me to enjoy my orgasm. Then with no warning she pushed her finger into my virgin asshole. She stroked two more times and I simply exploded. I shot 7 bursts of cum all over her shirt.

It took me some time to recover, Ruth waited patiently. Once I came back to my senses she took my hand and led me to her shower room. She had me stand under the water while she was sitting on a stool facing me. She took a razor and started shaving me, first my arm pits, then my pubic hair and balls and finally she asked me to turn around and bend over so she could shave my asshole area. I was completely smooth now. She said I looked very feminine and she seemed to like it.

She let me shower and when I returned back to her room she put the cage on my cock, gave me a kiss on the cheek and said "Three Months."

The first month was very hard, but I tried to do other things like focus on my studies, I stopped watching porn completely in order to suppress my sexual drive. I ignored girls because I could not admit I was in chastity to any girl my age. Then the summer vacation arrived and I had to go home for 2 weeks. I was sure Ruth would remove the chastity, but she firmly refused.

"Three months, young man." She told me. "You know what to do the next time you are facing the choices. Make the right choice next time, a punishment is a punishment."

The two weeks at home were hard, I had nothing to do and could not help watching porn which made me extremely horny and frustrated. After 2 weeks I returned to Ruth's house, I was so happy to return, I missed her a lot.

When I entered the house Ruth was wearing white bikini panties and a tight white sports bra, her ass and small breasts looked amazing. This was a view I had never seen before. She was so sexy, my cock got as hard as the chastity allowed.

I said hi and smiled, Ruth came toward me and kissed me on the lips.

"I really missed you, sissy boy." She said.

My mind was racing, I had to go on for another month and a half, it looked impossible that moment. I wanted to explode, I was willing to do anything.

"Ruth, I will do anything you ask. Anything. Please let me cum." I said.

Ruth smiled at me.

"Of course you will, baby. It was just a question of time from the beginning. But you need to go all the way. There are no shortcuts, and by the way, next time you ask me to let you cum before the time is up you will be punished."

I was on vacation, alone with Ruth, she teased me all the time with the way she was dressed and her sexy behavior. It drove me crazy, I regretted the decision I made that day on the chair.

The last week of my 3 month sentence arrived, I had one more week to go. It was Saturday night and I was in my room when I heard moans coming from the living room area. I went outside to see what is going on... Ruth was watching porn in the living room.

She noticed me.

"Come, join me. I am watching some sissy porn, you will like it."

On the screen there was a smooth young man in chastity sucking the cock of another man.

"Look how wet it gets me." She said and widely opened her legs. Her panties were soaked. "Do you want to smell them?"

I was going crazy, I wanted to ask her to cum, but she said not to do this or I would be punished, I nodded.

"Yes, please. Please let me smell them."

She took them off and put them on my nose.

"From now, till next week you will wear my panties over your cage, nothing else." Ruth said. "That is, if you want to get the three choices next Saturday. "

The man in the porn movie came and the sissy swallowed his cum, every drop, and moaned.

"See, he likes it." Ruth said, smiling. "I love cum too, pity I will not be able to taste any."

On the night before my release I could not sleep, I wanted to cum, I wanted to please Ruth. I didn't want to eat my cum. I knew that this was a decision that I would not ever be able to reverse.

Morning came, I was awake, I was waiting for Ruth to call me. She took her time, I was scared. I started to think she wasn't going to call me at all. Then at noon I heard, "Come over sissy boy!"

My heart was racing, my cock was trying to get hard in the cage, my asshole was pounding... it was time to cross the barrier.

Ruth was in a thong and sports bra, smiling.

"Come sit on the chair."

She tied my legs to the chair, and my hands behind my back. She said that I would not be able to handle this hand job without being tied firmly. This got me a bit scared, I had no idea what she meant by this. Once I was tied she removed the cage. My hard on was immediate. Ruth started massaging my balls. It felt so good, but I wanted to cum.

"You did not cum for 5 months, young man." Ruth said. "This is not going to be an easy cum. I am going to drain all the cum that your balls produced."

She started touching my cock, slowly and with very little pressure. It was amazing, I moaned strongly. Ruth said that my moans were very feminine and she loved it. She increased the pressure and I was on the edge of cumming almost immediately. She knew that, so she stopped... my hips tried to move, it looked like I was fucking the air. Then a bit of cum came out. Ruth smiled.

"This is what we need." She said. She cleaned my cum with her finger and put it in my mouth.

I was on the edge of exploding, the cum taste was so bad but I wanted to cum so badly.

"There is going to be a lot more of cum for you to eat." Ruth smiled. "Should I continue or do you want to go back to the cage?"

"Please let me cum! Please!" I cried.

She started stroking and the cum just burst out, one strong shot that hit my face. Then she paused for a few seconds and started stroking again, I shot more and more, I was completely covered with cum. Ruth smiled, she was glowing.

"Wow, I did not expect that much cum." She smiled. "We just started."

Ruth took a spoon and collected some of the cum. Then she fed it to me. It tasted so bad, salty. I didn't like it, but she kept going. 3 full spoons. I was still so hard and Ruth started jerking my cock again. After 10 minutes I came again, but she didn't stop. I screamed, my cock was so sensitive it was unbearable but she kept on going until I came again. She fed me the cum, all of it. I was exhausted, sleepy, and after a while I fell asleep.

I woke up to a finger going deep into my ass. I opened my eyes. Ruth's face was serious. She felt my balls.

"There is still cum inside your balls." She said. "It is time to get it all out."

She jerked me fast, I came in a few seconds and she kept going till I came once again. This time the load was very small... I was drained.

Ruth untied my hands.

"Well, clean yourself." She said. "You are a cum eater now, we both know it."

I reluctantly did as she said, and ate all the cum that I ejaculated a few minutes before.

Ruth then took me to the shower, she entered together with me, it was so arousing but I was scared to get hard because I knew this means more jerking and I could not take it anymore. She washed me, then shaved me.

"I want you to be a good sissy boy and lock yourself now. I think you want to be caged, don't you?"

She was right, I wanted her to control my cock, I didn't want to be able to masturbate alone or get a hard on without her anymore. I took the cage and put it on my cock, locked it and gave her the key.

So 5 months after Ruth caught me jerking off I was an obedient submissive sissy.

From that point I was released every weekend, I had to eat my cum every time I ejaculated. I still hated the taste, but could not wait for the weekends.