Author: Rick1616

When I was a senor in high school during the early 1970’s, I was on several athletic teams and very popular. It was a small city in Vermont. Having sex with the really nice girls started at age 18 and I had a bit of a reputation. Everything was going great until my Dad got transferred in January. I didn’t want to move and my parents agreed to let me finish high school. I was to stay with a woman named Jean who the family had known for years and I had done some small jobs for in earlier years. She was in her early 40’s and word had it she had been engaged twice, but never married. She was tall and had a Nordic look with fairly long blond hair. Her hips were nice and more of a rounded butt than you would expect. She was always dressed very proper and she reminded me of a teacher. She was rather plain looking but I remembered her as having a wonderful smile. I understood later in life that my parents paid her very nicely for my room and board which she welcomed. She did administrative work at a nearby college.

After my parents moved and I started living with her, things went well for about three days. Her 2 bedroom home had a generous size bathroom but there was just one bathroom. She had a long talk with me about how things were going to be. First, the bathroom was not to be locked. Next, it was inevitable that we would be in the bathroom together. We were going to have a relationship somewhere in between “brother/sister” and “husband/wife.” Finally, and with some difficulty she said that occasional nudity was one of her norms and didn’t want to change just because I was living there. I didn’t have to go nude but she didn’t want any prolonged stares at her if she was naked in the bathroom. She went on to say that as two level headed people, our situation may be unique but seeing each other’s body parts should not create a situation requiring other than normal behavior.

I really looked forward to seeing her naked---but what about no stares. Hmmmmm. So it did go better and we used the bathroom together in the morning. I did see her nude but it was mostly seeing her back and butt which I must admit was much finer than I had hoped for.

The typical morning started by me entering the bathroom, peeing, showering, shaving and doing the normal bathroom activities. I usually came out of the shower and put a towel around myself after drying off. She would come in about the time I was showering and brush her teeth, pee, and jump into the shower after I had finished mine. The glass doors of the large walk in shower had a molded effect so you could see nudity but not detail. I could see her pubic patch but no vagina.

She would emerge and dry off about the time I was finishing. Most of the time she turned her back to me and I would watch indiscreetly as possible using the mirror to catch the reflection of her and try and get a clear shot of her fine ass and nicely shaped legs. Occasionally she would bend over to dry her lower legs which gave me a nice view of her snatch and a wonderful mole on the inside of her right thigh. She too would wrap a towel around herself, covering her nice breasts and down to her mid thigh. At first I could feel a hard prick rising which I would mentally fight off. Then, I got kind of use to it. She didn’t say too much in the morning but was always very pleasant

This went on for several weeks. Then on a Saturday morning, we both happen to sleep in. I got up, brushed my teeth, peed and headed for the shower. Shortly, Jean came in and did the same. I finished and came bounding out of the shower with a big good morning. I was standing very naked and her back was to me but she could see me in the mirror. She was wearing a shorty night gown with a lacy top. She looked better than I think she felt.

I dried off and kept trying to make conversation. She was pretty non verbal. I started to shave while standing there with a towel wrapped around me. Then she blurted out. “your breath is awful…what have you been eating?”

“Pretty much the same stuff you have.”

“When was your last BM?”

“Can’t remember”—I might have been annoyed she was asking

“Just what I thought. Look, there are three solutions. Take a laxative, let me put a suppository up your butt, or let me give you an enema.”

Yikes—how did we get to this point so fast. None of those appealed to me but the pill sure sounded best. “I’ll take the pill.”

“Actually is Milk of Magnesia.” She quipped. You know, I think you should try a suppository. “

With some determination, I said, “Let’s go back to the laxative.”

“All right, but the suppository is the real easy way out. It’s not like I haven’t seen your whole entire body. Are you not liking the part where I put it into your butt?”

“I have never done a suppository before.”

“Let’s try it and see what will happen. They work more often than not. I use them myself.”

“What happens if it doesn’t work” I asked.

“Then you’re getting enemas—3-5 of them.”

She was searching through a drawer for the suppositories and found them. She showed them to me and explained how she would be sliding one into my rectum, holding it in place while it melted and then I was to wait until I had a strong urge to go. She held up her middle finger and pointed out that it was well clipped and filed. She then unwrapped the suppository and showed it to me. She knew all too well that this whole thing was a totally new experience.

“OK Rick, time to turn around and lean on the vanity.” So I reluctantly bent forward and put my hands out.

“Lean on your elbows silly.”

I complied and I saw her search a drawer and finally she came up with a tube of KY.

“I wish I had a latex glove—Oh well, I’ll just have to wash afterward.”

She took up a position behind me. She untied the towel which fell to the floor. Next she started to put lube on the suppository and I strained to watch her in the mirror. She was bent forward giving be a great down view of her breasts.

Exciting as it was, it kind of deflated as she instructed me to lay my chest on the vanity and reach around a spread my cheeks.

“Spread your legs apart Rick…Spread your cheeks really good for me. You have so much hair that I need to see what I am doing.”

I complied never having felt this vulnerable to a woman before—not even my Mom. Just then the suppository was pressed against my anus and in it went. I felt her finger go in slowly as she pushed it into me and then she held it there. After a good 30 seconds or so, I felt her exploring around. I felt my insides fighting back against the intrusion. Discomfort was setting in and I wanted this to be over

“Boy, I wish I had that glove—you are really stuffed.”

“Then I felt a real weird sensation and my hips came forward a bit. “

“I just wanted to feel your prostate. I never have done that to a man before. I hope you don’t mind…did I hurt you?”

“I just want this to be over…are you about finished back there?” But she held her finger in me for another two minutes explaining it had to melt inside of me and not pop out. Then she withdrew her finger ever so slowly. She took some tissue and wiped me which truly embarrassed me. Don’t worry…I made a little mess back here and I need to clean it up.

A slight smell of poop started to permeate the air. She told me to hold everything in for at least 20 minutes. She said the suppository would attract water from my body and enable me to have a BM.

“Gee, Rick, I feel a little embarrassed that I took the liberty to check out your prostate. You aren’t upset with me are you???”

“No, I’m not sure where my prostate really is myself…if that is what you touched, I guess I know now.”

“It was firm and quite pronounced…you know, that’s where your semen is stored. I guess it means you are ready for action…a devilish chuckle followed.”

I got dressed and went out to get breakfast. I felt cramping so I went back to the bathroom. Not much in the way of results. She heard me flush and came in to the bathroom and started the 20 questions treatment. She wasn’t convinced it had really worked.

“I’ll give you until tomorrow morning…if you don’t have a really great BM by then, we’re into enemas. Of course, I’m thinking the bulb type being squirted in my ass. When she said 3-5 enemas, I thought 3-5 refills. I knew I could handle that since my Mom would give me at least 5 refills when I was 9 years old.

“Don’t worry Jean—my mom have never paid that much attention to my BM’s. I think you may be freaking out over this.” No response from her.

I went out with the guys that night—after all it was Saturday. Sunday morning I got up with a slight hangover and went in for my usual pee and shower. Guess who was waiting for me when I got out and was drying off.

“I am beginning to think you like watching me standing here naked and drying off. You know I am just a VISITOR here”

“Never mind the bull. She stepped closer. Your breath is worse. And she turned and left.

I put on jeans and a sweat shirt and went out to fix breakfast. Pretty soon there was a call

“Rick, would you come back here please?”

I was just about finished and casually walked back to the bath. I entered not seeing anything unusual …whoops…what is that can and all the hose. The can and hose I spotted weeks ago in the linen closet but didn’t know what it was for.

“Rick, I am going to give you a series of enemas. Have you had enemas before.” I explained yes but is was a squeeze bulb and my mom would refill the thing a few times and repeatedly slide it in my butt and I would feel the water squirt in.

“Now you’re a man. It is time for a man size enema. This tube has a special end with special holes” –she held it up for me to see. “ I will slide it in your rectum a few inches or until it won’t go in any further. Then I will start the flow of solution and keep working the tube into your colon. It doesn’t hurt—I do it all the time. If the water goes in up high in your colon, you have less urgency to expel—and that’s what we want. I usually take about 2 quarts with very little difficulty. A big guy like you would normally take more but we’ll start with two. Any questions?”

Yeah—you talked me into that suppository thing, but I am not doing an enema like this. This is not what I usually do.”

“Nonsense. Don’t be a wimp. You are going to get several enemas. I forgot to mention, the first one has some mild soap in it and the rest will have a little baking soda.

“Not me—not right now. Let’s wait a couple of days. Everything will be OK—it always is…”

“What is your problem?" I have seen your entire body. I put my finger in your butt. Help me out here?”

“I have been constipated before—everything comes out in the end—excuse my pun.”

“YOU have horrible bad breath. It is not your teeth. You --young man are full of shit! Everyone around you, starting with me, is sick of your bad breath.”

“I’m going to go see some friends. See you later.”

She stepped in front of me and blocked my way. “Sounds like a great idea! After I have are cleaned you out. DROP YOUR PANTS!!! NOW!!”

A strong piercing stare turned to a glare wilted me. I hadn’t seen this side of her. My heart was racing and my mouth was getting dry. I tried staring back but it didn’t work. I turned and dropped my pants. “Your underpants too Rick!” She quipped.

I complied. I turned back around standing there with just a sweatshirt on. My dick felt more exposed somehow than it ever had before. She had not gotten dressed yet and was still in her nightie. I could see down the front but stealing a glance of her breasts was not a much fun as it was usually. She had placed a folded over towel on the floor. Your can kneel or Lay on your back.

“Sounds like you are the Big Mama in charge here…why don’t you tell me?”

“That comment was unnecessary—I want prefer you on your back. Put your butt on the towel.”

I was not in the mood for this. I was embarrassed my dick was laying there right in front of her. Somehow this should not be happening to me. She placed a small blanket on the floor and told me to lie back all the way. She took a very warm wash cloth and got down in front of me. I was totally exposed and under her full control.

Spread your legs apart and draw your knees up to your chest. I barely got my knees up a she slapped the washcloth right against my asshole. It felt surprised but it did feel good. As she bent over, I stole more glances down the top of her nightie and she knew I was looking. She got a towel for herself to kneel on and additional one for under my hips. She finally was kneeling in front of me with her nightie hiked up high on her thighs.

“Use your hands and hold your knees back tight.” She had already filled the can and there were a few soap bubbles floating around the top. This time she did have latex gloves and put on her right hand... Then she put a huge glob of KY on her middle finger and came at me. I tighten up. She pressed against my anal sphincter but did not enter. Her finger started circular motions that began to feel good.

“Rick, relax honey. You have to let me penetrate you a little. It’s going to be easier than the suppository.” Her tone had softened considerably.

I tried to relax. First she presses her finger in an inch or so and held it. Then further. Then back out to the circular motions. Then back in…only deeper. I wanted to expel her finger.

“Gee Rick; your prostate is really larger today.” She tried a forced little chuckle in an attempt to relax me.

I didn’t know what to say. Soon her finger came out and she readied the hose by explaining she was letting the air out to make me feel more comfortable.

“OK--- knees way back now.” She was leaning way down to get visual contact with my ass.

With one motion, the tube was in me a good 2-3 inches. The she kept feeding it in. She stopped pushing and released the clamp. I felt nothing at first. Then she started pushing the tube in and in further. Occasionally, she would pull it back 2-3 inches and then push forward. I could see her stare at the hose but she would also look at my nice sized dick. Occasionally, her left had would brush against my penis and I wasn’t sure how to react. She appeared to be all business.

“How far is that thing in me?" Just as I said that I could feel the water rushing around in my abdominal area.”

“You are close to 15 inches. I have little marks on the tube every 6 inches. I want to go at least 24 inches.”

She was stopping every so often to pinch the tube. She then would let it flow for about 10 seconds and pinch again. This went on and on. Pretty soon a huge cramp came.

“OK—that’s enough—I have to go.”

“Easy Rick." You’re not even half way there. Put you legs all the way down.” Then she clamped the hose

I put one leg on each side of her. With her left ungloved hand she palpated what I now know is my colon. Slow movements down low just into my pubic hair all the way up to just my sternum. The cramp subsided but I felt my dick starting to come to life.

She saw it and ignored it at first. She started the flow again. This went on for some time. The grimace on my face signaled a cramp and she would react by a gentle massage of my stomach.

There was the tube in my ass, the water in my colon and her hands doing there thing. Add to that nice views of her boobs and my dick was almost at attention.

“Rick, of course I see what is happening to you. It is quite natural for arousal to happen. Just let it happen. It may me hard for you to accept, but I have seen a “hard-on” before you know. I am getting a little excited myself. You are a real good looking guy with very nice hardware. I was very surprised with the conversation

She is getting excited. I didn’t know 40 year old women got excited at the site of a 18 year old kid. Something strange here. Anyway. my penis decided to go back down.

She stood up and looked into the can. “Oh’my gosh..You’ve taken over two quarts.”

Just hold on for another few minutes. And I did. The way she positioned herself at the vanity, I could see most of the way up her nightie. My dick reacted and I was back up at attention. She caught a glimpse and did not seem to know what was causing it. But she was enjoying it as it went to it’s full 8 ½ inches and kind of laid back on my stomach.

I am going to remove the tube. Here is some tissue I want you to press firmly against your anus to make sure everything stays in. When you get on the toilet, don’t worry about the noises or the smells. Rub your colon in reverse of what I did—start high and work low. It will take a good 10 minutes for you to expel.

My dick subsided—almost back to normal. “Raise your knees up.”

She slowly pulled the tube out. And then pushed some tissue against me. She helped me get up and turned on the exhaust fan as she left. I went, wiped and flushed repeatedly. I was very surprised how my poop and water was coming out.

I let go and did everything she said. I had a very strong urge to jack-off but did not. Fifteen minutes later she came back in. Now fully dressed.

“Doing OK?”

“Yeah—Fine.”

“I think for your next one, you will get on your hands and knees.”

“I thought there for a minute, I was done. Gee, I feel much better. I think that is enough for now.”

“I knew you would say that.” She was wiping down the hose and refilling the can. You have a bunch of soap inside of you. I need to rinse you out—and you still have stuff inside that needs to come out.

I did the final flush. I resisted no longer. She positioned everything so I was on my hands and knees. She took up a position be hind me. She put on another latex glove and I felt her relubed my asshole. I was enjoying the anal contact. Soon the tube was being inserted—further and further. The flow was started and she pushed in more and more.

Last time we went in about 20 inches. Nearly all of this 30” hose is in now so you are really going to get a high enema this time. Get down on your elbows—better yet go all the way down to your chest.

The whole process was repeated and cramping was not an issue until the end. With her dressed and me with my face down, there was no stealing glances of her legs and breasts.

“Rick, I am so proud of you. You have taken more than the last time.”

Back to the toilet and another 10 minutes to expel completely.

Again she returned with all of her questions. “Rick I think I will give you just one more small one. How do you want to be—on your back or on your knees?”

“I’ll just lay on my back.”

She took up the now familiar position. Soon the lube was being applied and the tube inserted. A little faster than before.

“I’ve got a question for you?”

Go ahead. She was so confident that she had done this to me and got past my resistance. I could tell she felt in control of me.

“Who gives enemas to you?”

“I give them to myself.”

“Then why do you have to give them to me? I could do this.”

“Because I want to make sure they are done right.”

“So, hypothetically, if I need an enema again, I should give it to myself?”

“We’ll cross that bridge when we get to it.”

“Did you clear this enema stuff with my mom first.”

Panic was on her face. “Why no Rick." I thought our relationship was mature enough for this to be just between us. Your mom knows that living like this is going to have certain discrete aspects—don’t you agree?”

“Sure. But I think you should let me do the same thing to you someday.”

“It’s not going to happen—it’s a private thing for me.”

“I don’t get it. Private for you and not for me…”

“Rick, we’re getting very hypothetical. I am giving you a great education here. Knowing how to do this will be good for you as time goes on. I still have more to teach you.”

The enema was flowing and it was difficult to concentrate on talking

“Listen Jean, I can and want to give you an enema someday. That would be instructive too. You must admit, I have let you do this to me without too much resistance. I know you are doing the right thing---I’m just asking for a chance to return the favor. You must admit, having someone help you with an enema is better than doing it yourself. My dick started back up.

“I sort of detected a thank you in there somewhere. And you are right—an enema by yourself is harder than having some help.”

“Can you just hold the possibility out there as a “Maybe?????”

“OK—Maybe…anything is possible.”

“You are a beautiful woman. I have come to realize you are very attractive. I agree I am getting an education. But you would have to agree, doing the real thing to you would be education for me too.”

“Well, thank you for the compliment Rick. I suppose it would be an education for you—I just haven’t gotten to a place where I would let a 18 year old give me an enema.”

“You know it was you that turned me on. That long hair, your blue eyes, and that wonderful smile makes things happen.”

I kind of guessed that. You turn me on too—I have very natural desires too you know.

The enema finished. When I was done she said there was one more thing. She got out a tube of cream and had me bend over the vanity. My asshole was sore and she knew it. Soon she was applying the lube ever so gently to my asshole.

“Easy Rick—I need to massage this in so you will heal back there.” I got a real good hard on and she kept massaging my entire anal area. Looks like the anal massage gets you excited too—maybe even more than my pretty blue eyes.” A definite devilish chuckle followed.

“Are you going to be OK? I feel I have really turned you on with no outlet!

“I’ll be OK.”

That night, after I heard her brush her teeth she came into my bedroom. She had a nightly on but this on was shorter than I those I had seen before with a low scooping neckline showing cleavage down her chest. I was laying nude in bead with the covers up to my stomach.

“How do you really feel about today—you know, the enemas and all of that. Was I too aggressive with you?" Do you feel better inside?”

“I am horny—very very horny.

“Typical answer for a man. I guess that is to be expected. I would be lying if I said I was not horny too.” She scooted slightly closer and looked at me. “That much touching and looking really gets my juices flowing. There is something else. You made me rethink your questions about my own enemas—that is, whenever I do give them to myself. You know, I would be honored if you would help me out. We could keep the whole thing our secret—very very private—just the two of us. We have a good relationship and I would be OK if you were to touch me back there if it were for an enema.

My heart was pounding. “This is really something. I don’t know what to say.” My dick was so hard , the covers were rising. “You have got to stay with me now—how about a little sex education too—“

I reached up and pulled her toward me. She eagerly leaned forward. She would not let me kiss her on the mouth—but everything else was OK. She taught me about oral sex given to a woman and soon she placed a condom in my hand—she had been holding it the entire time. After several minutes of me giving her oral sex, I put her in the missionary position and I slid my penis up and down her vagina making sure to stimulate her clit each time. Soon there was a rise of emotion so I let my 8 ½ inches slide straight in until I contacted her cervix. I held there and waited for her bucking movement to slowly start. I positioned myself so my dick was doing a good job on her clit. I continued to pleasure her and a very strong orgasm followed. Soon I was filling the condom. We talked afterward about what had happened and we were both anxious to do it again. About 2 AM she left my bed and I went out like a light.

When morning came, she went to work and I to school---almost like nothing had ever happened. However, after that Sunday, our morning routine was much more relaxed and certainly more nudity on her part. About a month later, she came in and awakened me and asked me to come in and giver her some help. She was dressed and had been up for a while. When I entered the bathroom, the enema can was there and everything ready to go. She looked at me and simply told me to get to it . One big difference, she wanted me to undress her to get ready for the enema. I slid her slacks off and then turned her around to slide down her panties. I started to help her into position for the enema and she told me to take off her top too. Very arousing for me and she loved it. I helped her completely nude body into a position on her back. She put her arms up and hands folded under her head. She had that “come and get me now “ look. I took up a position in front and helped push her kneed back. I lubed my finger massaged her anal sphincter nice and gentle very much to her pleasure. The tube was slid into her and I ended up giving her two enemas very slowly. The session ended very similarly…I screwed her so good she shook the entire bed.

After that, she knew that anytime she wanted me, she would just visit my bedroom. She would stand by my bed, I would toss off the covers and sit up in bed and face her. I would raise her nightie up past her breasts and gently kiss the bottom side of her breasts. Soon, she would fall over on top of me and things would really begin. I was very careful to make sure her needs were met and she to mine. She loved to finish on top…I think she liked me to be submissive but aggressive. While we did not do anal sex, she would allow me to touch her anally as long as I would be sure to lube her first and then keep that hand away from her vagina. My favorite was reverse cowgirl with smooth anal stimulation for her.

These were memories for life