Phyllis.

Phyllis
I never dwelled long on thinking about circumcision, at least not after high school. I remember in gym class, I would sneak sidelong glances at the other boys to see what was dangling between their legs. Some of what I saw looked like a baby elephant’s trunk, as mine did. Others had round knobby heads. Of course, I learned more from the usual anti-Semitic jokes. Circumcision was something that others endured and was nothing I would ever have to be concerned about. All that would change when I became involved with Phyllis.

I met her at work. It was one of my earliest jobs after graduating from college. She was assigned to help me on a project and was very nice and helpful to me. In a short time we formed a cordial and professional relationship. She was in her early forties and I was twenty-five. I thought she was very youthful and very pretty. Her voice was as mature for any woman her age; it was without the whine that is so prevalent in younger women. She had straight white teeth and healthy pink gums; she was not a smoker. She had hazel eyes and her hair was red with greenish highlight that makes it sparkle. Her skin was white with a light bluish under cast, without any blemishes, although she had a mole on her left cheek. It was about the size of a pinhead and it enhanced her beauty. She had an athletic build; she jogged and played tennis often. She would wear glasses for close up work. I would stand behind her and inhale her clean smell. My eyes would wander across the back of her neck. There was the urge to brush my lips across the smooth flesh. I soon developed a crush on her. She told me she divorced her second husband about two years ago in another state. She had one child by her first husband, whom she had married just after high-school. The child, a daughter, who also married young lived in another area. Phyllis was alone in an apartment near our office. I told her very little about myself.
Eventually, she asked, “Are you married?”
“No,” I said, my face getting warm.
She looked at my reddening cheeks and smiled.
“Really?” she went on, “You’d be a nice catch for some girl.”
My face got warmer, “I guess I just haven’t met the right one.”
“There are so many single girls around, I’m sure you’ll be snatched up in no time.”
I would smile; I enjoyed the bantering even when she would ask questions of a less personal nature.

We had finished the project and she invited me over to her apartment for dinner; this was her way of celebrating. I asked if I could bring anything and not surprisingly she suggested red wine to go with the roast she would prepare. It was a delicious meal and the wine made my mind race. I helped her wash and put away the dishes. Even though I was thinking what it would be like making love to her, I managed not to break or drop a single dish. She invited me to stay and watch television. I accepted and sat on the chair while she sat on the couch. My heart pounded when she invited me to sit on the couch with her, saying that I would have a better view of the screen. I sat there barely paying attention to the television. She laughed heartily at one of the jokes and to my astonishment her head was on my shoulder. Soon we were sitting close and holding hands; I was in pure heaven. I leaned over and she offered her lips to me for our first kiss; I knew then that I was in love. She pushed me back and put her lips to mine, I felt her hand move to my stomach. I soon had a throbbing erection. Slowly she pulled my shirt up and I felt her hand on the bare flesh. She messaged my stomach and with each stroke her fingertips slid further under my belt. I was intoxicated by her smell and gentleness. With her left hand she unbuckled the belt and I could feel the zipper opening. She slid her hand under the waistband of my underwear and took hold of my cock. I loved the feel of her hand. The erection got even harder as she started stroking it gently. In a few minutes she brought me to an orgasm.
“I’m sorry,” I stammered.
“That’s alright,” she said, “Now don’t get up, I’ll get a wash cloth.”
She came back with the wet face cloth and towel to wash the semen off her hands and me.

The next night I was over at her apartment again. The television was on and she invited me on the couch.
“I hope we are not going through what we did last night,” I said.
“Why, what do you mean?”
“I don’t want to play around, I am a grown man. I’m too old for games.”
“I’m sorry you feel I treated you like a child.”
“I want to have a relationship with you like a man and a woman should have.”
“In other words, you want to have sexual relations with me.”
“Yes,” I said, “I am grown up, after all.”
“You have the right to expect more than what happened last night.”
“Well, what is the problem? Is there something wrong with me?” I asked.
She got serious, saying, “I want some kind of a commitment. Would you want to move in with me?”
“Yes,” I said, looking her in the eye, “I would like to move in with you.”
My eyes opened wider, when she said, “Hmm, then we need to have you circumcised, first”.
I stammered, “What?”
She smiled, “If we live together we are certainly going to have sex.” Her smile disappeared, “I don’t want to have sex with someone who has not been circumcised. Both my ex-husbands had it done before we were married. It’s no big deal.”
“I don’t think I want to be”, I objected.
“Don’t you want to live together?”
“Well, yes, I do.”
“Then, I’m afraid you’ll have to be circumcised.”
I sighed and lowered my eyes, “I can’t believe we’re having this conversation.”
“Look, I like you, I think you are sweet. All I’m asking is that you be circumcised, that’s all. It’s for health reasons, for my health.”
“What do you mean by, for your health?”
“Women who have sexual relations with a circumcised partner have a lower incidence of cervical cancer.”
“Phyllis, I just don’t think my health insurance will cover it. It is elective surgery. Isn’t it?”
“I know your insurance won’t cover it. I’ll take care of the expense.”
“How much is it going to cost you?”
“Don’t worry about it, Al, I can cover it.”
I sighed, “OK, OK. If you want to pay for it, I guess it is no big deal.”
“Good, now it’s settled. I can make the arrangements.”
After what seemed like a long silence, I nodded my head saying, above a whisper, “I’d like to think more about it more.”
“Very well, if you decide to go through with it, you’ll need to take a week off from work. That will give you time to heal properly.”
Puzzled by her last remark, I asked, “Are you going to call an urologist?”
“No, we don’t need one. My sister is a nurse back home. I helped her do it to my both my ex’s. I can give her a call and ask her to come out. She can do it here.”
“You mean right here?” I asked not knowing what else to say.
“Yes, right here, in my apartment. You can stay here while you heal.”
I stared at her and she looked back waiting for my reply.
“When would you need an answer?”
“Let’s shoot for a month, if you decide to go through with it, I’ll call my sister.”

All I could think about the next day at work was circumcision. A couple of days later some of the guys at work were talking about what it felt like. One co-worker related a story how he had it done when he was stationed in Greenland in the military. Apparently, he wanted to have it done there. In his words there were no women within a hundred miles of where he was stationed. So, he felt it was a good time. I winced when he grimaced saying, “God, I was sore for a long time.” I went home, after work, feeling sick to my stomach. I knew that the guys realized that I was seeing Phyllis regularly. I didn’t want them to think I was considering it by asking too many questions but I wanted to know as much as possible.

A month had gone by when I arrived at her apartment one evening. She answered the door as usual but turned away and walked ahead.
She stopped, turned toward me, asking sternly, “Have you been thinking about what we discussed?”
“You mean about
me getting circumcised?”
She said in a huff, “Well, that’s what we’ve talked about, isn’t it?”
“Oh”, I said. “I don’t know if I can go through with it.”
“You told me you loved me, didn’t you?” she said, exasperated. “Didn’t you mean it?”
“Y-yes” I said.
“I would think you would do that for me. It is important for my health.”

The next night I went to her apartment. She met me at the door and acted happier than I’ve ever seen her.
“Hi, Sweety!” she said kissing me as I stood in the doorway.
I was surprised as she is usually discreet when showing affection. I knew she was going to bring up the subject of my being circumcised. I was right.
She said, “My sister and I circumcised my last husband in our apartment.”
“Isn’t that kind of risky?” I asked.
“No. It’s a simple procedure. As I told you before my sister is a nurse. She has seen many circumcisions both on infants and adults.”
“Isn’t it painful?”
“Of course not, we’ll use an anesthetic. It will be a little uncomfortable during the procedure. It may be sore afterwards but you’ll be fine.”
I looked at the floor and sighed.
Her voice became more soothing, “Look, it is alright to be afraid. I’ll be there with you. Just think of all the great sex we’ll have afterwards.”
The thought of making love to Phyllis made my fears lessen.
“We’ll observe strict hygiene, there be no chance of any complications. Oh, I’d be so happy, if you’d agree to go through with it.”
She looked so radiant, her voice so sweet I began looking forward to it.
“When can we have it done? M-my circumcision, that is.”
I had to say the word out loud to get used to the idea.
“I’ll call my sister tomorrow. I’ll find out when she can come.”

The next day at work she approached and said in a whisper, “I called my sister. She said she’ll be here the fifteenth of next month. You’d better talk to the boss about getting that week off.”
I couldn’t look her in the eye, I said, “OK.”
I felt her cool hand on mine and I looked into her eyes.
“Don’t be afraid, it’ll be all right,” she said with smile.

I was at her apartment every night up to the time my leave was to start. We would watch television and kiss only. If I got too excited she would smile and say, “Not until you’ve been circumcised. I would just sigh, saying something like, “You don’t know how much I want it.”
“No,” she would say. “We have to wait. I’ll get rid of your erection.” She would slowly undo my pants and give me a hand job.
She would look at me, smiling, “This is nothing like the real thing, believe me. I’m glad you enjoyed it, Al, but it doesn’t do much for me.”
“I’m sorry.” I stammered. “I can’t wait ’til we get this over with.”
“Neither can I.” she would purr.
I began to look forward to the day when we would be living together. I think we would both be relieved.

When the last day at work before my leave was to start I was mentally prepared. I dashed over to her place after work. To my surprise, Phyllis was not there. I woman answered the door. She looked like she could have been Phyllis’ twin only she was looked a little bit older. I assumed it was her sister.
“Oh, you must be Al. Phyllis has told me so much about you. I’m sorry, I’m Betty, Phyllis’ older sister.”
“Is Phyllis going to be here?” I asked.
“Yes, she will. She is out getting some medical supplies that I’ll need.”
“Right now?” I gulped.
“Yes, I’ll circumcise you tonight, so you need to take a shower. When you come out, wear this.” She said handing me a white bath rope.
I gulped and did as she asked.
“I want you to wash your penis real good but there’s no need to shave your pubic hair, OK?”
“OK” I said obediently.
“Pull the foreskin back and kind of scrub around the head.” And then she winked as she said, “Unless you want me to come in there and do it for you.”
My face got warm and I stammered, “N-no, thank you.”
I took my clothes off and looked down at my organ. I remembered back in high school taking gym class where some of the boys in class were circumcised. I remembered how funny theirs looked. Would this be how mine was going to look? This is the last time I’d see it like this. I stepped into the shower and the fear started to come back. I thought about Betty holding it in one hand with a scalpel in the other. The thought actually gave me an erection. To some men it is an erotic fantasy to be circumcised by a good-looking woman. Tonight it would be no fantasy but a reality. How many men would want to trade places with me? Would I want to change places with any of them?
I heard Betty call through the door, “It’s alright if you want to masturbate. It’ll be a few weeks or so before you can use it for anything but peeing”
I thought I heard Phyllis’ laugh in the background as well as Betty’s. I scrubbed it down just as Betty had asked. I watched the water run off the end of it. Would it run off the same way next time? What would it feel like? I finished the shower, dried off, put the robe on and timidly walked down the hall to where I heard them talking. They were standing by the coffee table.
“Take off the robe and lie here on this coffee table,” Betty said looking at me.
There was a clean sheet over the table and a pillow for my head. I removed the robe, let it fall at my feet and stood there stark naked. She didn’t look at me.
She patted the pillow and said, “OK, now lie down with your head here.”
She was holding some cloth towels draped over her fore arm. I did as she asked and closed my eyes. I felt her binding my ankles and wrists to the table. My heart was pounding in my chest.
I open my eyes when I heard Phyllis say. “Don’t be afraid, everything will be all right.”
Phyllis left the room and opened the door to her bedroom.
“You can come out now, we’re ready to start”, she said into the room.
Three women from work came out. Two held their hand to the mouths to stifle a giggle. I recognized all three. I closed my eyes in embarrassment.
One said, “Gee, I’ve never seen a man’s penis before.”
Phyllis laughed and said, “Come on, Karen, you got to be kidding.”
“No,” Karen said, “I’m not. I’m serious.”
One of the other women said, “Really, Karen? You mean you never did it with, your boy friend, Jerry?”
“No. I mean, we petted a lot. I’ve felt it through his pants but we never did it.”
“Do you ever touch it? Betty asked.
“No, Jerry is too religious.”
“Do you want to see what one feels like?” Betty asked.
“I don’t know,” Karen said glancing at Phyllis.
“Oh, go ahead but wash your hands first, Karen. I don’t want you infecting my, eh his dick.” Phyllis said laughing.
They all giggled.
“Wash your hands with that iodine solution, while I give him a hard on.” Betty said as she gently and slowly stroked my organ.
Betty was right, I soon got a hard on. I closed my eyes when I saw Karen approach.
“Did you wash those hands?” Phyllis said.
I heard Betty say, “Yes, she did. Go ahead, Karen, touch it.”
I felt her fingertips on my hard and throbbing organ.
“It’s so warm.” Karen giggled.
“Wrap your hand around it, Karen, give a stroke or two.”
I have to admit I enjoyed the feel of Karen’s hand.
“I’m getting jealous, Karen, that’s my property.” Phyllis said with a laugh.
“Do you want to see what it looks like when he comes?” Betty asked.
“Now wait a minute, there.” Phyllis interjected.
“Oh, let her jerk him off, Phyllis, we can clean it up. Besides that will be the only pleasure he’ll get all week.” Betty said.
“Yeah, go ahead. Do it.” The other two women said.
Karen started to stroke my penis almost mechanically.
“That’s not how you do it. You’re not trying to pump water.” Phyllis said, “Do it gently like this.”
I felt Karen let go of me. I opened my eyes and saw Phyllis take my organ in her hand. She looked at me and smiled.
She turned, looking at Karen she said, “See, Karen, gently, like thi
s.”
“God, Phyllis, knew how to do it.” I thought.
“OK, OK, now let me do it.”
Phyllis released me and Karen took over.
She looked into my eyes and asked, “How
does that feel Alfie? Are you enjoying it as much as I am?”
For reasons I could never figure, Karen always called me Alfie, not Al like everyone else.
I smiled, closed my eyes and let her bring me to an orgasm.
She let go quickly as my prostate contracted. I opened my eyes and saw some of my semen on her hand.
“Wow, that was something.” Karen giggled.
All the other women laughed.
“Aren’t you going to thank her, Alfie?” Phyllis laughed.
“OK, girls, it is show time.” Betty said, “Let’s get down to business. Karen, you clean up the semen. Wash you hands in that iodine solution again. Pull the foreskin back and clean the head of his penis.”
“It’s deflated,” Karen laughed.
“I’ll give him another hard on and put this clamp at the base so it’ll stay hard. That will make it easy for you to clean. Meanwhile, Phyllis and I will make up the anesthetic.”
Betty began to message my lower back.
“Wow, look at it, it’s getting hard again,” Karen said.
I winced when the clamp clicked shut at the base of my cock. It hurt a little at first but felt better afterwards.
“Good, now get cracking, we don’t have all day.” Betty barked.
Karen then pulled back my foreskin and swabbed the head with that reddish-brown liquid.
“Oooh, you’re having too much fun, Karen.” Phyllis smiled as she pulled on a pair of rubber gloves.
“Leave her alone, Phyllis, she’s doing a good job,” then Betty said to me, “Raise your ass up a bit, Al, so I can put this pad under it.”
I raised my buttocks an inch or so off the table as she slid the pad under me. My ankles and wrists strained against the bindings.
Betty put on robber gloves. Phyllis watched and smiled approvingly.
“Good job, Karen, thanks. Now, stand-back a ways. You can stand close enough to watch. I’m ready to start.”
I closed my eyes, resigned to the fact that this beautiful woman is going to circumcise me as a lay bound to a coffee table.
I heard the other women say, “Wow, Phyllis, she’s all set to do it.”
“Yes,” Phyllis said, “Now get on either side of him and hold him by his thighs.”
She looked at me, smiled and said, “This is going to sting a little bit.”
Betty was holding my penis between her thumb and forefinger with one hand and with the other, gently formed my foreskin over the plastic cone. It was the strangest feeling I ever had. I felt my legs being pulled further apart. The plastic cone felt tighter. I winced and heard one of the women holding my legs giggle. What I thought was the first cut was a sharp sting to the head of my cock. I opened my eyes to see Betty inserting a needle with a syringe with something into its head.
“Hold on to his legs tight now.” I heard her say.
I sucked in my stomach and squeezed my eyes even tighter in response to the pain of the needle.
“Oh, God, that hurts.” I blurted out.
“It will take a few minutes to go numb.” I heard her say.
No sooner had she finished talking when my organ felt like it was ice cold.
I opened my eyes and saw Betty take a scalpel and start to slice my fore skin from the top. It just peeled away and the head could be clearly seen. I would have been more fascinated it didn’t hurt so much. Even with the anesthetic it stung like fire.
I closed my eyes even tighter and could feel my foreskin being sliced away. I started to moan. I felt Phyllis’ hand on my cheeks. She was standing behind me saying, “Be brave my darling.”
“I want to see it,” I heard one of the women say.
“Stand here and hold him down, Dora, you can see it up close.”
I was writhing in pain.
I heard Karen say, “There is not much blood is there?”
I don’t remember how long it took. It seemed like hours. I writhed in agony as Phyllis gently swabbed my forehead with a clean face cloth.
She would whisper, “Shh, it’s going to be OK. Oh, I love you so much. Be brave my darling.”
I heard Dora say, “Looks like that foreskin is coming off in one piece. You are good with a knife Betty.”
“Hold him down tighter, Karen, he is moving too much.”
“I’m trying but he keeps wiggling around.”
“I know but you have got to hold him still.”
“Oh, Alfie, please be still.”
I remember blurting out, “Please, Betty, give me a little break, it hurts.”
“She is almost done, my darling, be brave.” Phyllis cooed.
I don’t know how long she operated on me but she finally said to no one in particular. “I’ll just suture it and it’s finished.”
“I love you so much, for this.” Phyllis said.
“Good job, Betty”, one of the women said.
“I wish my husband could be circumcised.” Dora said.
I opened my eyes and looked at my cock; it had bright red ring around the head. It looked like one of those space ships they use to put satellites in orbit. I was finally circumcised.

I moved in with Phyllis. It was about six weeks later before Phyllis and I finally had sex. God, it was worth all the pain and the wait. She was right; sex with a circumcised cock was great. I had experience with sex in high school with a girl from my homeroom but it never was this good.
Later that week, Karen stopped me in the hallway.
“How is it going?” she asked.
“Fine,” I said.
“Did you heal up nicely?”
“Yes, “I said, “But it was sore for a few days.”
“I asked Jerry, he’s my boy friend, if he was circumcised. He said he wasn’t.”
“Oh,” I said, blushing.
“I told him if he wanted to marry me he would have to submit. We broke up, just as good I guess.”
“That’s too bad, sorry to hear it.”
“I’d like to see yours sometime, you know, see how it’s healed and all.”
“Phyllis would not like that.”
“She wouldn’t have to know, I wouldn’t tell her. After all, I’ve seen you naked already.”
For the next couple of days Karen would badger me to let her see my circumcision.
She stopped again in the hall way.
“Watching you being circumcised was such a turn-on,” she said.
“I didn’t think women would enjoy watching a guy get cut,” I replied.
“Oh, it is, believe me. I got wet every time you squirmed and moaned.”
“Really?”
“I’ve become friends with Betty. She’s going to do her daughter’s boyfriend next week.”
“She told you all that?”
“Oh, yeah, I’m flying back there to help out.”
“Gee, Karen, you’re really getting in to this, huh?”
“Yep, Betty’s going to teach me how to do it. That’s why I want to see how well yours has healed.”
Just then Phyllis appeared.
“What are you two whispering about?” she asked accusingly.
“Nothing”, we said.
“It better be nothing.”
That night when I got home, Phyllis had a box on the table.
“Know what this is?” she said holding up a leather and metal device.
I shuttered, I knew exactly what it is.
“Yes,” I said, “It’s a male chastity belt.”
“Right,” she said, “You are going to wear it and I’m going to keep the key.”
“Why?”
“I don’t trust Karen. That cock belongs to me. It cost me a lot of money to fly Betty out here.”
I blushed and looked down at the floor.
“Karen is not going to get her hands, lips, tongue or anything else on that penis. It’s mine and I am not going to share it with any other woman.”
She approached me saying, “Get those pants off.”
I started to unbuckle the belt when Phyllis grabbed the waistband and pulled them down,
“You’re too slow, get the shorts down.”
I let my shorts slide down to my ankles.
“Come here”, she ordered.
I waddled over to where she was sitting. She reached out and took hold of my cock.
“Hold still while I put this ring on you.”
The chastity belt was made of leather and metal, it had a small brass pad lock fastened to it. It looked like it could be removed with a bolt cutter but it but it would be painful on my testicles. If I removed it I could not get it back on. It hurt when she squeezed my testicles into the metal ring. Then there was a mechanical click, the device was on and locked.
“It stays on twenty-four hours seven days a-week, you can pee thr
ough it and wear it in the shower. You can show it to Karen if you wish, she can look but she can’t touch.”
“Does that mean no more sex?”
“You won’t be able to even jerk off with it on.”

I sighed in resignation.
“I can’t take a chance with you having intercourse with other women when you go on a business trip, either. There are so many sexually transmitted diseases out there. I don’t want you bringing one home to me.”
Then she said through clinched teeth, “If I so much as think you removed it, we will be through and you’ll be out on your ass.”
I wanted to object but I held back. I didn’t want to lose her after all I’ve been through.
“If we go a week or more without sex, I’ll give you an enema and with this tool,” she said, holding up a plastic tool that resembles a spatula, “and I’ll milk your prostate. This tool will make it easy. I can do it with the belt on you.”
“Won’t that hurt?”
“It shouldn’t, it’ll feel like you’re peeing. We’ll let it dribble into a cup.”
“Why would I need an enema?”
She glared at me saying, “It’s just good hygiene, of course.”

One time when I came back from a business trip, Phyllis was away for two weeks visiting her daughter. I missed her badly and could not wait till she returned. Finally, to my relief I got a phone call from her asking to be picked up at the airport. I was never so happy to see her. Her kiss felt great and I immediately got an erection. Phyllis was too tired from her flight so we didn’t make love that night. We didn’t make love all week. I complained, “Phyllis, I haven’t had it for three weeks and I’m as horny as hell.”
“I don’t feel like it yet. My daughter is having trouble with her husband.”
“Well, if we don’t get it on I think my balls will explode.”
“Your prostate probably needs to be milked. I’ll give you an enema and milk it tonight.”
She prepared a solution of baking soda and water.
“We’ll do it in the bathroom, so take you pants off,” she instructed.
I bent over and frankly enjoyed the feeling as she put petroleum jelly around my anus. She slowly inserted the nozzle and I could feel the warm liquid entering me. Soon my belly started to ache and it got hard.
“There,” she said, “hold it awhile then sit on the toilet and go.”
I groaned as my stomach ached and it was a relief to evacuate.
“Good,” she said, “now bend over again. I’ll use my finger to massage your prostate rather than that tool.”
I felt her finger slide into my anus and felt her putting pressure on my prostate. It felt strange as the semen ran out into a small cup she had me holding under the head of my cock.
“Wow, you were full,” she said.
She dumped the semen down the toilet and said, “I’m ready for bed. How about you?”
In a few days she got over her concern for her daughter and we were back to making love again. That was the only time she milked my prostate.

After a couple of months of normal sex, Phyllis shocked me again one morning.
“I don’t want to get pregnant,” she said looking me straight in the eye.
“It would not be good for a woman my age to bear a child. If I was younger it would be OK.”
I shuddered and knew it would be another operation I would have to endure. I loved her so much that before she told me what it was I said, “Yes.”

This time she made arrangements with an urologist; it was performed in his office.

Phyllis and I broke up a few years later. It wasn’t over anything in specific, we just lost interest in each other. I never knew what happened to her, she would be in her eighties by now. A bolt cutter was all that was needed to remove the chastity belt; I did it with no harm and little discomfort. I found an urologist who was able to reverse the vasectomy, as well. In time I met and married a wonderful woman. I have even fathered three children who in turn have produced seven grand children. My wife never asked me any details about my circumcision; I think she assumed it was done at birth. In time I have forgotten most of my ex-girl friends, not that there were many. However, I will always remember Phyllis.
Of course, I am reminded of her every time I go to the bathroom or take a shower.