However I was enjoying a fairly rich sex life with a variety of mistresses. The whole thing really messed with my head. One by one I lost interest in these young ladies, for no other reason than despondency, knowing that once castrated, the joy we shared would abruptly end. I used various excuses because I was very embarrassed about the real reason for the break-ups. Soon I found myself alone, and hornier than ever, and growing a bit crazy, for lack of a better word. Losing my mind, not myself, my work suffered; I had to take some bold action.

I placed a dating add on various pay websites. My goal was to find the impossible: a woman who was sufficiently attracted to me (and attractive) to rate sex; also one who is sufficiently cruel to carry out the necessary deed. I didn’t want surgery like my dad or my uncle. I wanted to go out in sexual triumph, making a scene and a memory that would last me another 30 years. Alt.com made logical sense because it attracts the bdsm crowd, dominants and submissives; however it consists mainly of pretenders and some really pathetic individuals. I tried several more sites, and out of desperation I tried good old Match.com, posting a normal profile. Finally I was corresponding with genuine females from my area, who accurately matched their photographs and self assessments. That is how I met Heather.

The thing Heather hears most from strangers is the question, “Oh wow, are you by any chance Naomi Watts?” I thought the same thing. Her resemblance to the actress is remarkable. But unlike a bankable actress, my Heather is dead broke. With two lovely young children in tow, she had divorced and that unfortunate deadbeat chose not to honor his manly duties to her and the kids. Consequently she had to raise two kids by herself while working in a department store selling men’s clothes. She was barely making ends meet. In her I figured I had found a perfect opportunity for castration.

After about eight dates, it was she who started hinting at the sex issue. We sat on her couch making out, and she was squeezing my junk through my jeans when I placed my first trial balloon: “I’d be honored to let you cut off my gonads.” She looked at me like I was crazy. Next time she opened my fly and freed my raging erection. I unbuckled and pulled down my pants freeing everything, shaved smooth and clean. She appeared pleased, seeing everything for the first time, and I said “Heather, I’ll give you my goodies but not in the way you’re thinking.”

Her face changed. “What the fuck am I thinking?” she demanded.

“Sex, a secure loving relationship,” I said, watching her blink at me in shock or disbelief. “I want them off. Heather, I want my balls off. I want you to fuck me every which way, then one tiny little slice.”

“You’re fucking CRAZY!” she said, rising from the couch. I grabbed her wrist and she yanked but I held firm. Our eyes met; she seemed confused, angry, and more than anything, confused.

“I’ll pay you ten thousand dollars; twenty-five hundred now,” I said, flipping twenty five Ben Franklins onto the couch, “the rest after you get it done. You drop me at the emergency room afterwards, I’ll tell them I got mugged, they’ll file a police report, and be looking forever for a pair of young male criminals. You absolutely cannot lose.” I then explained the whole cancer situation, and she sat back down. I started getting a little bit misty-eyed, and she actually held my hand and put her head on my shoulder. I pulled down my pants again and she started fondling my cock and balls, making me hard.

“Such a shame, I can’t believe this. I finally meet a nice guy on Match and it turns out he has cancer. My luck,” she said, crying a little. “When do you want to do this?”

My heart started pounding. I felt sweat forming low on my back, the kind of feeling you get when you’re about to go on stage or enter an IRS audit or criminal trial. I swallowed. “I have a bag in the car. Let me get it,” I said, and returned a moment later with an Elastrator, antiseptic, disposable scalpel, soft rope, medical tape, gauze, a small but impregnable reinforced steel lockbox with a key sticking out of it, and a few sex toys. I opened the bag to give Heather a peek. Her eyes grew wide. “Now, Heather.”

Her eyes narrowed. “How do I know you’ll pay the balance?” What a great girl, I thought, thinking of her kids first. It’s the only way I could ever find a normal attractive girl to play along with this, I realized it, the transactional nature of it. I smiled as I pulled out seventy-five hundred-dollar bills and placed them in the safety box, turned the key, checked to make sure it was locked, then I literally ran out of the room into her home. I hid the key deep between her young daughter’s mattress and box spring, then returned before she could figure out what happened. “I hid the key in a place you are not likely to find. If you do this, I’ll tell you where to find it on the way to the E.R. and if you fail to keep your promise, good luck finding it. Now here, take the lockbox and hide it wherever you like.” Which she did, then returned.

“Let’s do it,” she said. “Show me what to do.” I undressed and we practiced putting tight green bands on my scrotum, then cutting them off with small round-nose scissors. When she announced the had the hang of it, I placed the materials back into the bag, took a deep breath, picked up the bag, and followed her into her daughter’s bedroom. “I don’t want to do this on my bed,” she said, which I sort of understood. The bedroom was in a young girl’s motif, and the bed is a twin. Heather placed the plastic painting tarp on the bed and covered it with the sheet from my bag. Using the bed legs, she fixed my wrists first, then using two longer pieces of rope, I tucked my knees to my chest and she affixed them to the same legs. My genitals and anus were completely exposed to her. I tested the ropes and they loosened a little, but she re-tied them until I was absolutely secure.

Heather undressed. This was the first time I’d seen her naked and she was everything I had fantasized her to be, albeit her breasts drooped a bit from breastfeeding to kids, but it did not detract. Her thin hips and flat stomach were free of stretch marks. Her pale skin was truly flawless. Her legs long, her feet narrow and pedicured, callous free. She used one of the green bands to tie back her hair, and with her stylish black eyeglasses she was truly a vision of dominant female perfection. I knew I had chosen wisely as she sat on my face looking down at my eyes. “Lick!” she said simply, and lick I did. I used all of my skills, and Heather smelled and tasted every bit as good as I imagined, musky and tangy but not overpowering. She tasted healthy and delicious, and I swirled and lapped, nibbled and sucked until she came in my mouth. She dismounted and laid the contents of the bag onto a towel on the floor to the right of the bed so that I could see. I watched her grab the inflatable vibrating butt plug which I had purchased but never tried. After a few sprays of KY, she shoved it in my ass and it hurt, but just for a few seconds until my body adjusted to the intruder. She squeezed the bulb and I felt it tighten inside my ass. She flipped on the vibrator, and my cock jumped in response.

Heather snapped on a pair of latex gloves, and her perfect ass was inches from my face – deliberately I’m guessing – as she bent over and retrieved the Elastrator, Crazy Glue tube, sterile gauze, and the plastic-packaged scalpel. I gulped. She straddled my face backwards this time and planted her anus on my nose, of which I inhaled deeply. Her wetness sank onto my mouth, and I needed no prompting yet she said again, “Lick me, lick me harder this time.” She writhed forward and backwards upon my tongue. I just let it happen, my tongue enjoying the mixed flavors and sensations of waxy anus and velveteen silken vagina. As she did, she engulfed my swollen cock in her mouth and started bobbing, swallowing me skillfully, using her hands on my balls and cock to simulate the sensation of sex. Heather is good. She’s no stranger to the male sexual response. She gave the butt plug two more squeezes and that nearly triggered an orgasm right there, which she sensed, and stopped. She didn’t come either and I could tell she was close, her petals open to my mouth and juicing in a pre-orgasmic way.

My cock was still raging when she flipped off and deflated the plug then wiped off my balls with gauze soaked in antiseptic. I could see the lust in her eyes. This was no longer just a business transaction for either of us. She knelt on the floor to use the Elastrator. After opening the green band she stretched my balls through it and pulled very hard as instructed. My anus clenched around the plug and I yelped, and then the band snapped down at the bottom of my sack. She stretched the second band and painted the inside with the Crazy Glue, then snapped it closer to my body, leaving a space between the two bands. My balls hurt but not terribly yet, but the pain was slowly growing more intense. I could see that my sack was turning plum colored. Heather used more antiseptic on that pencil-thin canal of flesh between to two bands, and the little minx actually grinned at me as she ripped open the plastic and freed the glinting scalpel. She was into it! I was starting to get really scared by this point. I said, “OK, I’ll tell you where the key is. Stop, I can’t do this.” My balls were dark purple and killing me. The pain was affecting my mind.

“No, that wasn’t the deal. You predicted you might try to back out and told me to proceed no matter what.”

“I didn’t mean it. The deal is off.”

She picked up the roll of duct tape and ripped of a six inch length, placing it over my mouth. “You told me to tape you and I have. Don’t be a wimp. Cancer, remember? Now I’m going to give you the last and best fucking of your life!” she said, carefully arranging the scalpel off to her right on top of the antiseptic gauze still on the corner of the bed. She got on all fours, reached between her legs, grabbed my limp cock and started stroking it. All I could do is moan into the tape and gaze at my purple sack and her skinny ass. The fear and pain made it almost impossible to get hard, but one last fuck was part of the bargain and she was intent on seeing this thing through. She reactivated the vibrating plug, and I recall her giving the inflation bulb ten full squeezes. My ass was full, the pressure and vibration on my prostate undeniably stimulating. I actually fought against erection, but it was fruitless. I was completely hard.

Heather guided the tip inside and sat back hard, which rocked my super-sore balls, but her bright pink, warm velvet canal enveloped my aching cock and mitigated the pain. I don’t recall penetrating a woman ever before feeling that exquisitely good. She knew just how to rock up and back to make me delirious, and from her increasingly delighted squeals and breathing it was no secret that she was truly enjoying herself. I guessed that this is what I had really wanted after all, and I just stared at her split-open beautiful privates, breathed in her musk wafting up, and retreated deep inside my pleasure. She could tell I suppose from my cock and from my noises that the time had come. I didn’t even notice her retrieving the scalpel. The waves of exquisitely sharp pleasure hit me gradually not all at once. It truly was a unique climax for me, in retrospect; nothing like it ever before, maybe because my balls were so confined. The first wave felt so good it was painful, but I noticed something odd: all pain in my balls was suddenly gone. I heard her squeal and felt her dozens of slick inner silk fists contract hard on my cock as she too came hard and fast. My waves came in slow motion it seemed, one… then another, each as good as the last, and I felt a tugging and the knife – a brief and sharp feeling of pain – yet still drowning and thrashing in the greatest relief of my life. But all good things must end, yet I felt energized and wonderful, really. She kept me impaled inside of her until my cock dwindled back to normal. At that point she dismounted quickly, pulled on a pair of sweats and a tank top, then unzipped my tape and untied my ropes. I looked down and saw the glued rubber ring still clasping the pencil-thin shaft of meat that once held my scrotum.

She helped me into sweats and socks and sneakers, helped me to my car, drove me to the hospital and parked in the visitor lot. I had the hospital number pre-programmed into my cell phone and she reminded me to call it as if I’d forget. I still felt giddy and energized and yes the pain was creeping in but not as bad as you’d imagine. I’ve had sprained ankles that hurt ten times worse. “Where’s the key?” she asked, giving me an all-business look. I told her. She said nothing further, shut the driver’s door and disappeared on foot. I never saw Heather again nor communicated with her. Although sometimes I walk past the men’s section of the department store just to remind myself of that last and best experience as a fully functioning man.