Ben’s second date with Anna leads to much pain and pleasure
Sitting at the table outside the cafe I waited for my date. A blind date to be precise. My friend Ted had set up the date for me as I had been single for a long time. “What’s she like Ted?” I asked and he replied “She’s your type of lady”. I liked all types of women so his description didn’t tell me anything.
I was told to hold a book so the lady would know who I was. Looking at my watch she was late so I decided to read the book. About twenty minutes later I heard a quiet voice say “Hello are you Ben?” Looking up I saw this beautiful Japanese lady. No taller than five foot with a round smiling face, long black hair and wearing a jacket and skirt. Standing up I replied “Yes I’m Ben and you are?” “I’m Anna. Sorry I’m late” she said holding out her hand so I shook it and said “Please sit down Anna”.
The waiter came out and took Anna’s order then we started to talk. Apparently she has been single for a long time too. She knew Ted through his wife as they were friends. She has lived here since leaving Japan when her parents emigrated. She works in a ladies clothes shop and enjoys movies. I told her about my job in computing and that I enjoy movies too. By the end of the date we agreed to meet on Wednesday and we exchanged phone numbers.
On Wednesday morning Anna messaged me to ask if I’d like to go to her home this evening for drinks and I replied I would love too. Wearing a new white shirt and dark grey trousers I walked to her house which wasn’t far from mine. Upon ringing the doorbell she soon answered wearing a navy blue dress that was close fitting. “Hi Ben. Welcome to my home” she said and I replied “Thanks Anna for inviting me”. I could see she has small pert boobs and when I followed her into the lounge my dick stiffened when I saw her curvy little bum. I sat on the sofa while she went and got us some drinks.
When she came in with the drinks she sat close to me and we talked about our days then Anna said “I know we’ve only began dating but would you like to go to bed?”. Somewhat taken back I stuttered and said “Well yes if you want to” so she took my hand and led me to the bedroom. “Undress and lay one the bed while I get changed” said Anna as she went back out of the room. I was still hesitant as I hadn’t been with a woman for a long time still I took off all my clothes, put them on a chair near the bed and layed down naked. I gave my dick a couple of pulls so it would look bigger and waited for Anna.
When she eventually walked back in I was very surprised at what she was wearing. A black pvc body suit and a mask covering her eyes. The zip on the suit was pulled down a way showing off her cleavage and I felt some stiffness in my dick. She walked to a drawer and took out a box and bought it over to the chair where I put my clothes. Removing the lid she pulled out four pairs of handcuffs and proceeded to cuff my hands and feet to the bed. I was nervous and aroused at the same time and then she pulled out a round ball with a leather strap. Unsure as to what she would do with that she promptly pushed the ball in my mouth and put the strap behind me head.
Anna was smiling at me as she put her hand in the box and pulled out a riding crop. Standing by the side of the bed she began to gently smack my chest and my thighs with the crop which felt quite pleasant. However she then smacked down hard on my chest and I grimaced with the pain. She did it again on my stomach and then on my thighs and I was shouting in pain though it was muffled by the ball in my mouth. Anna looked at me and smiled again before lifting the crop high and bringing it down hard and fast on my dick. As I screamed into the ball with pain and tears were in my eyes Anna hit my dick again just as hard and I thought I would pass out.
She looked over at me and perhaps realised she had gone too far. She rested her small cool hand on my soft painful dick and stroked it gently. The pain started to ease then she leant over and kissed the tip. Putting the crop back in the box she pulled out what looked like two metal clamps on a chain. Wondering what she would with them I soon found out. Anna put a clamp on each of my balls and they felt like they were being crushed. Then she pulled the chain firmly and my balls were dragged forward and I shouted into the ball in pain. Anna released the pressure on the chain then quickly yanked it even harder and I nearly cried with the pain.
Anna smiled once again at me then she removed the clamps and put them away and took out two small wooden paddles. She placed one under my dick with my balls underneath then she lifted the other paddle and whacked it down. Screaming again into the ball the pain was excruciating and I thought my dick was destroyed. Anna calmly removed the paddles and put them away before moving back to my dick. Leaning over she kissed the tip again before sliding her tongue along the shaft. This took my mind off of the pain and to my surprise it began to erect.
Once it had I could see it was bruised before Anna put her mouth over the tip and slid every inch of my shaft inside her. She then started to suck up and down and it felt lovely. Her tongue caressed all of my dick and her mouth was so warm and wet. The feeling of pleasure after so much pain was wonderful and I guess that’s why people enjoy this sort of thing. Anna began sucking faster and I felt my balls tingle and looking at her curvy little bum in her pvc suit was thrilling. Anna then stopped sucking at the top of my dick and began flicking her tongue against it. I moaned as the sensations in my groin as she kept going and I could feel I was close to orgasm. Just as she started to suck up and down again I started to shake and I groaned as I came hard into Anna’s mouth. She didn’t move away but calmly sucked all of the come out of my dick until my balls were empty. Sliding her mouth off my dick she stood and wiped the side of her mouth with her finger then she removed the ball from my mouth and uncuffed me. Putting the things back in the box she put it away before leaving the room.
My arms and legs were stiff however I managed to sit on the edge of the bed and pull my boxers and trousers on up to my thighs before standing and pulling them right up. After I put my shirt on Anna walked back in wearing her navy dress. When she was standing in front of me she put her hand around my neck and pulled me downwards so she could kiss me on the lips. Taking my hand she led me to the front door and said “I hope we can do this again soon Ben” and I replied “I’ll call you Anna” then we said goodbye. As I walked home my dick and balls hurt but I had enjoyed the blowjob. Would I call Anna and arrange another visit? I think I will.



