In my early teen years, I palled around with guy named Larry Snyder. He lived with his mother and his aunt, Gertrude Webber. Gertrude was a principal at an elementary school in our city. She was the sole support and indisputable head of that small three-person family. Gertrude’s build was thin and angular, her manners were impeccable, her English was perfect, and her demands for Larry’s behavior were without compromise.
When my parents went out for a late weekend evening, I was Larry’s guest overnight. Larry and I got along well and his aunt and mom were nice to me.
I met Larry at school in the first days of our seventh grade. In that we lived only a block apart, we often walked to and from school together. Early in our acquaintanceship, Larry remarked that he had had a stomach ache the previous evening and he had been given what he called a “Washing. A big red rubber bag with a long hose, you know?”
“An enema.” I suggested, with considerable interest. I asked who had given it to him.
“My aunt and my mom.” Larry answered.
“Did you like it?” I asked. In that the question was so unexpected, the boy was taken aback by its directness.
He stumbled a bit, but answered “Well, kind of…”
“Oh,” I interrupted, “I enjoy a good, warm, soapy enema. It always makes me feel so healthy.” I went on telling Larry how my mother used a black open-top bag, how she had me lie on my tummy, and how I enjoyed the whole procedure. I asked him a lot about the enema he’d received the previous evening ‹ like how big was it, the position he was required to take while getting it, if it had soap, and if it worked very well. He warmed to the subject enjoying his telling, in great detail, all about it.
As the kid and I got to be better friends, we talked about all the usual stuff pubescent boys discuss, like masturbation, which we called “jacking off,” heterosexual sex, of course, although it would be a long, long time before we had that experience, and enemas.
I was the first to volunteer the fact that an enema made my “cock long and hard.” Larry was eager to remark that his, too, got stiff when he got an enema and that, sometimes as he got the treatment, he’d “shoot.” If he didn’t do that, he told me, he’d “jack off” as he was emptying out.
“Doesn’t your mom say something if you shoot while you’re getting an enema?” I asked in amazement.
“No.” he replied, “besides, it’s usually my aunt who gives me an enema, and I don’t think she knows it happens.” In that Larry’s aunt was too sharp to miss much, I had trouble believing that.
One Friday evening of a weekend in which I was the guest of Larry and his family, we went to a movie at a neighborhood theater. We enjoyed the show so much that, when we got around to the place where we’d come in, Larry suggested we just sit through to the end.
“I dunno,” I remarked. “Your aunt just might be upset. You told her we’d come right home after this show. She’ll probably beat the shit out of you!” I said, only half in jest.
“Ah, fuck her!” said he in a most arrogant tone.
“I don’t think so, big-shot,” said I. “She’ll fuck you with a wire brush!”
“Nah. You’re fulla shit!” Insisted the kid. “She’ll have no way of knowing how long the movie was, anyway.”
I said nothing else, although I knew he’d underestimated the smart Gertrude Webber and I wasn’t too pleased about being told I wasn’t seeing the matter accurately.
When we did get home, Larry’s aunt and mother greeted us as we entered the apartment. That was the last his mom would say to us, absenting herself from what followed. “Good evening, Thomas,” Miss Webber said politely. “And to you too, Lawrence. You do know, of course, that you’re late.”
“It was a long movie.” stated Larry, with chin a bit too far out and manner a little too sure.
“Precisely. I know how long it was.” Said Gertrude with an edge in her voice. Then, becoming clearly angry, she continued “You would have been home twenty-eight minutes ago, but you doubtless stayed beyond the point at which you had come in. You saw the ending a second time. Did you not?”
“Well…” started the boy, now bereft of the arrogance of a moment before.
“Did you not?” she fired like a pistol shot. “No matter,” she said, with quiet firmness. “You disobeyed me and I will now punish you. I would like to punish you, too, Thomas, but since you’re not my child, I can’t. However, I will ask you to allow me to impose a penalty.”
This scene of Gertrude Webber’s anger had me shaken. I didn’t know what to say. I didn’t want to incur her disapproval, so I just answered with a tentative “Okay.”
“Then, Lawrence, you’ll go to your room, where you’ll put on your gray nightshirt in which you’ll receive a sound spanking and, Thomas, you’ll observe.”
Oh Hell, I thought, I’d be delighted to see Larry’s ass tanned. He’d been too damn cocky. And, besides, I’d get even with him for telling me I was full of shit!
Larry was now quite conciliatory as he pleaded with his aunt to not spank him and to, please, not make me watch. His pleas were, however, to no avail.
“Get upstairs, Lawrence!” his aunt demanded as she tilted her wristwatch into view. “Prepare yourself for your much-deserved punishment. You have three minutes from…now!” Then, in a more kindly tone, “And, Thomas, you go along and get into your pajamas and robe.”
Larry and I said nothing as we got into our night attire and he took a seat on one of the twin beds. His expression was a mixture of fear and respect as his aunt entered the room. He pleaded, “I know the lesson. You don’t have to spank me. Please don’t. I’ll never do that again. I promise. Oh, please!”
Oblivious to the boy’s begging, she sat down on the bed next to him and demanded he lie across her lap. She asked me to sit in a chair across the room. Larry did as he was instructed and his aunt lifted the tail of the nightshirt exposing his bare buttocks.
“Lawrence” she said, “you’re being punished for disobedience and arrogance. Your tone when I asked you about your tardiness, was defiant. I can’t have that. Were you trying to show your friend here how tough you were? You’re not that tough, are you?” she badgered.
“No.”
“Then take your punishment like an adult!”
Increasing the suspense, Gertrude allowed a few long seconds to elapse. Then she drew back her hand almost as far as her shoulder would allow, and she brought it down on Larry’s butt with an explosive crack! Almost immediately, Larry yelped and again, his aunt whacked him hard. She then allowed three or four seconds to pass between spanks as she continued to bring her open hand down on her nephew’s back side. Whack…whack…whack until his butt was a rosy red and Larry was crying loudly. Finally, she stopped.
I was aghast, but I noticed my young dick had developed a raging hard-on.
She instructed the boy to stand as she handed an open box of tissues from the night stand. “You know, Lawrence, your aunt loves you. She wants you to be a good, upstanding, humble person.”
“Yes, ma’am.” responded the boy, still sobbing and sniffing. “I’m sorry. I love you, too, aunt Gertrude.” It was a tender moment as the aunt hugged the sobbing adolescent.
“Now, we have another piece of business.” she said. “Your mother tells me your bowels didn’t move today. Or yesterday either, for that matter. Is that right?”
“Yes, ma’am.”
“Then, you know I’m going to have to give you an enema and, Thomas, as part of your continuing punishment, I’ll ask you to observe this event, too.”
Again, I was very pleased. I’d never seen anyone get an enema and it was with considerable enthusiasm which I believe I successfully hid so that I responded “Of course, Miss Webber.”
“Get the footstool from the living room, Lawrence. Thomas, do you need to go to the bathroom?” When I responded to the negative, Miss Webber instructed me to follow her into the bathroom where she gestured toward a short stool on which I seated myself.
This was, obviously, a routine Larry was used to. He’d mentioned the footstool once when he was telling me about an enema he’d received, but I didn’t quite understand just how it fit in.
Momentarily, he reappeared with the thing and placed it in the middle of the bathroom floor. From the linen closet, he took a part of an old plastic table cloth and a towel, which he placed, plastic first, over the footstool. Concurrent to this business, Miss Webber was removing from a drawer under the linen cabinet, the only thing in there, a dark red open-top enema syringe, with dark red hose and short, stubby, black nozzle.
The boy sat on the footstool while his aunt ran water into the tub, regulated it for temperature, and half-filled the enema bag. From the soap dish, she took a fresh bar of Ivory and immersed it in the bag. For a few long minutes, she worked the soap in her hand, dissolving a goodly amount in solution. She then filled the bag to over-flowing and I saw rich, thick suds spill down the side.
As she hung the bag on a hook next to the medicine cabinet and sat on the toilet seat lid, she instructed her nephew to “Take the position now.” The boy knelt at the end of the stool and lay across its length. He grasped the feet on the end opposite his knees.
I had a clear view of Larry’s still quite red butt as Miss Webber flipped the tail of the nightshirt up, swiped that stubby nozzle in a jar of Vaseline, and placed the greased thing against his anus. “Ready, honey?” she asked.
In a soft voice that cracked as though his throat needed clearing, he answered “Oh, yes.” Then with clarity, “Yes, please, Aunt Gertrude!”
With a twisting, pushing motion, she inserted the nozzle. My raging hard-on had returned as the woman clicked open the clamp. The snap seemed to startle the boy. She partially pinched the hose and I could barely notice the emptying of the syringe as she softly encouraged her young patient.
“You’re doing so well, sweetheart,” she’d say. “You’ll feel so much better when it’s over. Enemas aren’t pleasant, I know, but constipation’s miserable, isn’t it? Aunt Gertrude wants you to feel well.”
“Oh, yes. I know you do. Really.” said the boy. Evidently, he appeared to be struggling to take it, his grip on the front feet of the stool tightening as if in some desperation.
“I know it’s hard, honey. Since you’ve been constipated for two days, I put a lot of soap in this time and that makes it difficult, but you know it’s necessary to properly wash out those poisons. Take deep breaths, now. Does Thomas’ presence make you nervous?”
“No,” said Larry in between gasps with a tone of slight surprise. “It’s okay. But, please stop it for a minute!”
“Of course, dear.” assured Gertrude as she tightly pinched the tubing. After what was probably a full minute, she allowed a slow infusion to resume. I noticed her face was a bit flushed and her expression one of contentment. She seemed to be enjoying the task as she very slowly gave Larry his enema. With my hands in my bathrobe pockets, playing with my hard cock, I was enjoying the spectacle.
In what had probably been a good fifteen minutes from the time she started giving the cleansing, Larry seemed to be relaxing. He’d taken almost half of the bag. He took a little more before advising he could hold no more.
“I’ll help you.” said Gertrude as she snapped the shut-off closed and pressed the nozzle more tightly against the boy’s anus. She gripped his buttocks, pinching them together. She, almost imperceptibly and very slowly, slid the nozzle almost all the way out. Then she reinserted it.
I watched with great interest and excitement as she moved the thing very slowly in and out a few more times. In a short time, Larry seemed once again to relax.
“Okay now honey?” she inquired.
“Yes. It’s better.”
Snap! She released the clamp, the enema flowed unimpeded by her pinching fingers and Larry did some grunting!
At first, I didn’t understand, but I soon perceived Larry was coming! He was having an orgasm right into the towel under his dick. He was fairly quiet about it, but he still let out some rhythmic sounds for more than a few seconds. I saw the hose in his rectum wiggle and his aunt remark “That’s fine, Lawrence. Take your enema.”
“Oh, I…” was all he said.
“That’s fine, honey” his aunt, interrupting, assured him. I wasn’t quite sure why. If I saw Larry having orgasm I thought, surely, Gertrude did too. But maybe not. She clicked shut the clamp but continued to press the nozzle against the boy’s anus for a good minute or maybe even a little longer. “Now,” she continued, slowly withdrawing the nozzle and placing it up in the washbowl, “you may get up and expel.”
She stood up, flipped the seat lid open and Larry, holding the towel over his lap, stepped over to the toilet, sat down and began expelling.
“You’ll stay with Lawrence won’t you, Thomas?”
As I agreed to the lady’s wishes, I decided that, one day, I’d like it if I could get her to give me an enema !