I Need to Tell My Story Pt. 04

Note to the reader: It's best to start this series of chapters at Part 1, otherwise the narrative could be confusing.

Hi again, Manny.

It was funny sometimes, waking up in the morning, forgetting where I was and who I was. I'd lay there a minute or two before remembering that I now had a cunt and tits, a feminine face and long hair.

I'd get up and look at my smooth, slender arms, hands and fingers, and even admire my nicely shaped legs and ass!

After I'd seen that visual evidence, I'd return to living the life of Jackie. No more daily shaving, no more standing to pee. I'd be looking at the calendar to remind myself when my next period would arrive, so I could insert a Tampax on the right days. Yes, Froggie actually inserting a Tampax into himself/herself! Jesus.

That also, meant, of course, that I had to be careful not to get pregnant. Following my sister's wise advice, I went on the pill.

From time to time, I'd swear little feelings of Jackie's old personality crept into my consciousness, especially when I was looking at men and when I was picking what to wear. I found I was less interested in politics, and more interested in softer news about science and social issues. But I won't bore you with all that.

It came time for a second "date" with Lisa. As she and I had talked about, we went for a weekend walk in Holsum Hills park. We were both wearing jeans, me with a light pullover, her with a turtleneck sweater. She looked quite attractive, to be honest.

However! After I got her talking about her job and family, I detected she could be one of those non-stop talkers. Not exactly a motormouth, but someone who really needed a listener. Maybe there was no one at her work who filled that role.

So, I as Jackie became a listener, something Froggie was never too good at. I was nearing the end of my listening patience when we found a nice grassy area next to a bubbling brook where we spread out a blanket and lunch. Now we could talk more about food!

As we ate, I was attracted to her folded legs in her tight jeans. I kept looking at them and stole a glance at her crotch. And at her facial lips, which were slender but quite attractive.

She finally got around to asking about my male companion. That gave me a chance to relate the story of my accident and amnesia. I admitted that I was sort of resuming a relationship with Carlos, but fabricated the story that the accident had rejiggered my libido, so that now I found myself attracted to women, too.

Lisa lit up when I broached that subject again. I liked that. I chose to mention how I found myself attracted to her, and I'd swear she blushed a little. I asked if I could kiss her, and she nodded yes, so after we wiped the crumbs off our faces, I slid over and lightly embraced her and then looked into her eyes and brought my lips near hers. I let her come to me then, and we clumsily met for a moment before beginning to passionately kiss. My god, she was a hot kisser. Then came her tongue.

Our tits were tight against each other. I felt almost like Froggie again, getting into it with a willing broad.

When we separated, we were laughing because we were both out of breath.

"Wow!" I said, whistling.

"Yes. It's obvious you didn't forget how to kiss," said Lisa. "You know, I am so enjoying you, Jackie. I hope I didn't put you off by my babbling on and on."

"No, not at all, dear. I just figured you needed to talk."

Manny, I'm sorry, but sometimes I can lie my ass off. I was horny, and didn't want anything to get in my way of getting her into bed, that very day if possible.

After we wrapped up the remnants of our lunch, and put them in her knapsack, we continued walking on a trail, now holding hands. Hers were smaller, and warm, and we really felt a connection. It was almost like being back in high school again.

I was the taller and older one, so there was a little bit of the older-sister thing going on.

I had taken an Uber to the park, so she offered to drive me home "if that's what you want."

"Any chance we could go to your place?" I asked.

She lived in a smallish duplex, with a postage-stamp-sized back yard, where her two dogs resided, yapping at us. She treated me to wine and ice cream sandwiches. Here, I thought, is a true-blue working girl. Wine and ice cream.

Her place was on the messy side (admittedly, she hadn't known I was coming), for which she apologized. Nothing terrible, but there were dishes in the sink and magazines scattered around.

"Show me the rest of the house?" I asked. We climbed her stairs still holding our glasses of wine while holding hands lightly.

Wow, I thought. This is so much easier, woman to woman. I should've been Jackie ten years ago.

"So," said Lisa, "I converted this first bedroom into my workroom. I like to sew, and I even created this dress I'm wearing, should you want to know, and I dabble in some landscape painting in here. Just don't ask to see any of it."

"Sexy, very feminine dress," I assured her.

"And this is Sleepy Hollow," she joked as we walked down the hall into a second bedroom with a smallish bed, covered with a patchwork bedspread I suspected she'd sewn. It was actually quite well done.

At this point I carefully placed both our glasses on a dresser, and said, "Like to make out?"

She was slightly flustered at my forwardness, but managed a "Let's."

"This is only my second time with a woman," I said. "I mean, back in college I had this very close friend who lived in my dorm and had a single room. A couple nights we slept together. No big deal in college, right? I mean, we had a very sexy time, but it was never serious. Some other girls were doing it too."

And of course I was making all of this up! Not even Froggie did this. But I was trying to relax Lisa. And it worked, 'cuz we were soon hugging and kissing. Fortunately, her place was nice and cozy warm as I pulled down her dress to her waist to eye her bra. Then we kissed some more as I pulled down her bra straps to expose her perfect breasts and nipples. She looked soulfully into my eyes, as though we were converting to Buddhism or something.

She finally reciprocated by helping me slip out of my slinky top. While she was having a problem removing my tight sleeves, she whistled: "Oh my, I love your bra. I really should have one like it; mine are so plain."

Like a nurse, I told myself.

We kissed again, more passionately. She was getting enthusiastic, or horny, or something. I guess I was too, because I quickly stripped off my tight jeans, down to my lacy, black panties. I helped her out of her dress and panty nylons, until she was down to some flouncy panties with cute fringes -- the kind a tap dancer or square dancer might wear to titillate their partner or audience.

Again, Manny, I only truly began to notice these details when I became Jackie.

So, I led Lisa over to her bed and we lay down facing each other. I was glad we'd been drinking. I removed her bra and sucked on her wonderful nipples a little. She actually held her tits one by one to guide her nips into my lips. I had the weird feeling I was sucking my mom's tits as a baby!

At this point, I instinctively inserted my thigh between hers and pushed against her pussy. I was quite cunt-happy at this point, drawn to hers like a nail to a magnet, to put it in Froggie terms.

She began thrusting herself against my thigh aggressively. We were like animals. I reached back to grab her nice fanny and push her cunt even harder against me. We were embracing. She reached under my bra to play with my titty.

"I have always fantasized about having a nurse come on to me," I said teasingly.

"We should play doctor sometime," she whispered.

At this point we both undressed completely and slipped under the covers. As we lay facing each other once more, she reached down and covered my pussy with her delicate hand. I moaned.

"Mmmm," she replied. "Seems as though you have an extra-sensitive response to a gynecological exam."

"I should have one at least once a week," I quipped.

I pulled her to me tightly. She began kissing my forehead, neck, ears, shoulder, breasts, nipples, arms, fingers and belly button. Did I miss anything?

Now it was her turn to thigh-press my pussy. In response, I pulled my pelvis along her thigh hard enough to generate heat, I'd swear. For just a second, I was ready to pull out my dick and hard-fuck her until I remembered that I no longer had one.

In a lull, she reached down again to touch my pussy, inserting a friendly finger in there, to find my vagina and then my hard clit. My god! Within a half-minute of her circling it, I mightily came, convulsing and losing all control of my senses. At that point I felt very close to her, like I'd known her my entire life. Maybe we'd been joined at the hip as babies!

I snuggled up close to her and nearly fell asleep. I felt so warm and secure and ... calm. All the ruckus of becoming a Jackie fell by the wayside for a while. I was a woman.

After Lisa fell asleep for a time too (at least I think she did) we started up all over again, and I ate her out, and almost had another orgasm when she readily came. She really did have an attractive cunt, with just a tiny wisp of hair above. And she tasted nice, too. I really loved her kisses.

So, now we were an item, so to speak. I'd played with Carlos, but I'd gone all the way with Lisa. But there would be more to learn about her. I kept Carlos on the sidelines for a while.

The next time I met Lisa, we didn't even go through the formality of eating out. She invited me over for a pizza dinner with beer. She actually had made one from scratch and baked it in her oven, but the taste was rather bland. Gobs of cheese kind of made up for that.

This time, she wore a long, red-and-brownish peasant skirt with a loose, deep green velour top. The two actually worked together, I thought. Her hair flowed down over her shoulders, and she was wearing leather sandals.

After the pizza and beer, we watched a movie while cuddling, and caressing each other's titties. That's as far as it went. We ended up sleeping together, and in the morning (her day off, fortunately) we were horny enough to get going again. This time, she pulled out an unusual vibrator she used on me: It not only stimulated my clit, but the other part of it went up my ass around three or four inches! This was so unusual. Jesus.

I never realized my ass could be so stimulated. I came quite close to climaxing, but due to the unusual nature of the thing, I couldn't quite put it all together to reach the brink.

However, when she used it on herself, she moved it around quite a lot -- in and out of her asshole, and all around her clit, and she came easily, looking quite happy with herself.

"Well, that's something I've never tried before," I commented.

"One of my favorites," she said. She seemed happy that I expressed an interest in anal.

"This seems too early to tell you something," she said, "but we seem so close that I want to confess something. No, that's completely the wrong word. I mean that I want to share something. No, that's so corny. Just that I want to try something, if you're open to it. It's kind of one-sided for sure, and you need to be very honest about your feelings."

"Now you have me mystified. What's this big secret?"

"It's anal. I detect that you haven't done much with anal."

"True," I admitted. "I hear about people into it, but I've never been into it."

"And for me," Lisa confided, "I've done it solo, but never with anyone else. What we did just now was a first."

"So, now I'm ever so curious."

"OK. Have you ever heard of enemas?"

"Yeah."

"Like what have you heard?"

"Cleansing one's bowels," I ventured. "Like a medical thing."

"Yes. But I'm into it ..... sexually."

"Really? How? I mean, did you give it to patients and then somehow got hooked on it yourself? This is unusual."

"Well, yes, there was something about inserting a tube into someone's asshole that began to turn me on. Like, it was almost like fucking someone! And then watching their reactions as they were filled with liquid."

"I kinda see where you're going with this. And then you began to see how it felt when you did it to yourself?"

"Yes, exactly."

"So ..... you want to play with this, with me?"

"Well, I know it's a lot to ask, but I think I'd get an even greater pleasure when someone would do it to me. That's what I've fantasized about."

"Well, I haven't played with your asshole when we've made love. I suppose, then, that you wanted me to?"

"Oh, you don't know how much I wanted that."

So, Manny, the next time we made love (and before any enema play), I made sure to involve her asshole. I properly lubed my finger and inserted it into her hole. What a nice, tight seal that made around my finger! That really got her motor going, and she was practically purring like a kitten. I moved my finger around in there a little, and she backed her ass up against it. It was a little like a second vagina.

Then she tried the same finger thing with me. When I'd made love with guys in the past, they'd tried the same thing several times, but I usually ended up telling them I wasn't into it. Now, it was entirely different, with a woman. I liked it, especially since it had a forbidden or bad-girl aspect to it.

So, Manny, here's Froggie, I mean Jackie, the great experimenter, getting pulled into anal. Don't know if you've ever been into it, but read on .....

There was a week's delay before our next getting together late on a Friday. Of course this was at her place since she had the enema stuff. When I arrived she was practically aglow with smiles and warmth. This glow spread a little over to me, too, as we sat down to her usual pizza and beer, and a movie she streamed. I wasn't surprised it was lesbian-themed -- one of those slick flics with beautiful women with perfect bodies, beautiful tans and sexy lingerie. She just happened to pick one with some strap-on action toward the end, and boy, did that get me aroused!

"Jackie, I can tell that really turned you on, right?"

"Oh, yes. Yes indeed!"

"You noticed the one woman penetrated both orifices?"

"I gathered that."

"Like to try that sometime?"

"Maybe. Actually, I've never experienced being strap-on fucked. Of course I've entered myself using a vibrating dildo, alone. It might be fun to compare the different sensations for the different entryways, to use a euphemism."

"Well, my dear, if you want, that could be in your future."

"Mmmmmm. What a temptress you are."

We ended up petting again that evening, and just before we went to bed in our nighties, Lisa inserted a butt plug in herself with obvious delight, but I declined to do so. Still, as I lay there next to her as we fell asleep, I kinda wondered what one felt like.

I tell you, Manny, being a woman, and an attractive one at that, began to open all sorts of new avenues for me. I felt I could ride all sorts of new erotic adventures.

The next morning, now clad in bathrobes after breakfast, it was time for Lisa's long-awaited enema. I guessed that having the butt plug in overnight had somewhat sensitized her rectum.

After turning up the heat in her apartment a little, she pulled an apparatus out of her closet.

I won't go into all the fine details, but after filling a plastic bag with a warm saline solution (as she called it), and hooking it high up onto a stand, she showed me how I would insert the connecting plastic tube (ending with a sort of plastic plug) into her behind. She self-lubed her asshole, and lay on her tummy with legs spread, with the greatest joy and enthusiasm.

I was beginning to feel like a nurse myself when I inserted the "plug" into her, gently. She murmured and squirmed around delightedly for a moment before telling me to open the valve. I could see the liquid flowing down through the tube carrying a few small bubbles with it.

"Ohh, I think I'm in heaven," she said. "My asshole, and being occupied -- you just don't know what this does to me, Jackie."

I gotta admit, Manny, that the strangeness of all this and my administering the enema like a nurse, did end up turning me on. Got me wet. Not that I wanted an enema myself, but seeing her so turned on .....

Later on, after she'd emptied herself and was as happy as a clam, I decided to take her up on her offer later in the day. I was now enrolling myself in Anal 101.....

Would I ever tell her I used to be a man?