I was otherwise a late bloomer sexually. I had a girlfriend while in high school, but didn't get past second base with her. I think because my first sexual arousal involved anal stimulation with my mother, it made me somewhat confused and reluctant to try to engage in sex; I was, in fact, painfully shy with girls. I never tried giving myself an enema.

Ten years ago, in college, I met the Brooke, and we hit it off immediately. She was tall and trimly athletic, a year and a half older than me, not especially pretty, perhaps, except to me. She became my girlfriend for the next three years. Vastly more sexually experienced than I, Brooke quickly led the way and just as quickly realized I was a nervous virgin. This is a little embarrassing to admit, but I had some initial failures in bed. Well, I was a complete failure. I would be as hard as a rock with the preliminaries, with getting undressed and touching and kissing, but once it was time for me to penetrate Brooke, I'd become nervous and go soft.

Brooke said she understood, that we would take our time. But she didn't really understand until one night, after several misfires over the course of our first month together, she started some anal play, rubbing her finger around the opening of my anus, telling me to relax, that we wouldn't even bother with intercourse that night.

But from the sudden involuntary thrusting of my hips as she teased my anus, she realized what I liked. She slipped out of bed and returned with a jar of Vaseline. In the dark, I heard the top pop off the jar, and then the greased up fingers of one had were playing with my still flaccid penis, while a finger from her other hand reached behind my ass to find my anus again. In a few moments I found myself hard again, and then my girlfriend pulled my by my penis on top of, and swiftly inside her warm and slippery vagina. Her legs were around my waist, while two of her fingers, well-lubed, were buried just as deeply inside my rectum. Brooke moved her fingers inside me, in time with the up and down motion of my penis inside her. I could really only manage a few strokes, then I spasmed and came inside her.

Later that night, as we talked about how excited I'd been, Brooke wormed out of me my interest in anal play. It didn't take long before I haltingly admitted my early interest enemas. Brooke, instead of condemning me, was very sympathetic. She held me tight, called me her baby, and said we were going to just do what made us feel good.

In the coming few nights, we discovered that what made me feel good ­ her finger inside me - had a habit making me climax very soon, at least once I was inside Brooke's wonderful pussy. It would happen soon after we'd undress and climb into bed. She would bring out the Vaseline, then play with my ass for a minute or so, maybe while masturbating me; then I'd want to climb on top of her and I would quickly, too quickly have my orgasm.

"We're going to have to slow down, Dave" Brooke said one night, after I'd squirted before 30 seconds had gone. I blushed in the dark with shame.

The next night, Friday, we spent in her apartment. Brooke taught me how to 69, and we took our time playing with each other's genitals. Brooke, it turned out, also enjoyed anal play, so we played with our anuses, too. She was very careful to just tease my penis with her lips and hands, so that I didn't come for well over an hour, while I managed to help bring her to climax twice, my mouth on her pussy, and my index finger moving inside her anus. I couldn't exactly see her climax, because my face was pushed into her pussy both times. It was a novel experience for me, but I liked it. Brooke finally allowed me to explode in her mouth, while gently but relentlessly finger-fucking me.

"There's a lot more to sex than just straight fucking," Brooke said, when we were relaxed. I happily agreed, and then Brooke said she thought perhaps we could stay away from regular intercourse for a while. She shushed me when I started to protest. "We both need to be pleased, baby," she said, a finger across my lips. "Don't worry, you're going to enjoy whatever we do." She was right, of course and I blushed again, thinking I hadn't pleased her. Still, there was something disquieting about giving up what I thought of as a male right.

We slept late and then after breakfast we visited the drug store and came home with an enema kit. Brooke pulled the blinds, dimming the light in her bedroom a little. "We don't want the neighbors peeking in," she laughed. I was in a sexual frenzy. "We'll do you first," Brooke said. I quickly stripped while Brooke laid a few towels on the bed and filled the enema bag with warm water. I climbed into bed and lay on my stomach, and I had a tremendous desire to reach under myself, find my cock, and masturbate myself. I was too shy to do any such thing, of course.

"No, Dave," Brooke said. "Turn over, you can watch this and I want to watch you." In a moment I was on my back, and beautiful, smiling Brooke, now down to bra and panties, sat between my legs, which she pushed open as far as she could. She laid another towel on my stomach, and the enema bag went on top of the towel. Brooke had the now half-empty Vaseline jar open, and soon had two fingers working away in my anus, while her other hand, gooey with more Vaseline, gently stroked my penis. I was in heaven. I reached up to caress her bare shoulders, wanting her to take off her bra. I tried to reach behind her to release it, but she leaned back. "Let's just take care of you, first, baby" she said.

In a few moments, Brooke said, "Let's get going," and stopped playing with me to coat the enema nozzle with Vaseline. Then she was easily pushing the nozzle inside me, she released the clip and gently pushed down on the enema bag, and I felt the warm, soapy water begin flowing into me.

"Oh, that feels so good!" I told her.

There was something wonderful about being penetrated this way, about submitting myself to another person so intimately. Maybe this is how a women feels when she feels a penis ­ or an enema nozzle ­ inside her vagina or anus.

With one hand on the bag and the other guiding and working the nozzle inside me, my poor penis, still hard and now lying against my stomach, was now neglected. Brooke looked down at me and said, "Go ahead, baby, play with yourself for a while, I'm busy!" I felt my face blush.

"I can't!" I said emphatically.

"Don't be a real baby," she said. "Go on, it'll feel good and I want to watch you do it. Put some Vaseline on your hand," she added.

In a few moments, doing what she wanted, I was lost in a delirium, masturbating first slowly, then more quickly as I felt my orgasm approach, even as I felt my stomach distend with the continuing flow of liquid. I told myself that, with my lubricated hand, I was feeling what it would be like to be back inside Brooke's pussy.

It did all feel so good. I tried to spread my legs a little more, to let Brooke know how good it all felt, although I was still somewhat embarrassed. With my eyes closed, I continued to stroke myself, but the pressure from the enema bag suddenly eased, although the nozzle stayed in. I opened my eyes in time to see my girlfriend reach out with one of her now free hands, to pull my own hand off my penis. I groaned when she did that, but quickly she leaned down, and took the tip of my penis in her mouth. I tried to reach behind her to unsnap off her brassiere, but it was futile. Her expert lips and tongue brought me to the edge and beyond as she totally engulfed me: I shot my semen directly into her mouth, my hips bucking wildly, in the throes of another powerful, and this time masturbatory climax.

After I calmed down, the nozzle was removed and Brooke helped me quickly make my way to the bathroom. I exploded again, from the other end. It was the best enema I'd ever had. The experience literally left me shaking as I returned to bed. I wanted to reciprocate but Brooke said that would be for another night. I think she sensed my mental as well as physical exhaustion. In any event, she was now naked, too, and as we embraced beneath the covers, and kissed, she gently pulled me close and pushed a finger inside me, again. I don't know when she fished it out, but I fell asleep that way, enjoying the feel of her finger inside me, and her bare breasts up against my chest.

End of Part 1