I Wish She Hadn’t Ch. 02

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This is Part Two of a two-part story.


Madi stared up at me with a look that was equal parts astonishment and embarrassment. “John Jameson, what did you just make me do?” As if it was my fault! Then, she sat up in bed and reached for me, but before her hands found my face, she saw the aftermath of her eruption and stopped in her tracks.

“Oh god! I’m sorry! I’ve made a mess of you! Let me clean you up.” She grabbed a handful of the bedsheet and started trying to wipe my face with it while simultaneously she tried to make sense of what had just occurred. “I don’t know what just happened there, John, but it was simply incredible! What is this on you? Is it cum? I don’t know how much is normal, but it seems like there’s an awful lot! It’s all over your face!”

Whatever it was, some of it was still dripping off my cheek. I figured it was easier for me to do it, so I took the sheet from her and finished cleaning myself off.

A brief thought passed through my mind. Was Madi’s explosion a simple loss of bladder control, and perhaps, instead of cum, I’d just wiped piss from my face? It wouldn’t have bothered me, considering it couldn’t be explained as anything other than an involuntary physical reaction, but still, I was curious.

Then, I noticed that the part of the sheet that I’d used to wipe myself bore no discernible color stain. Whatever the fluid was, it was either clear or kind of whitish and had no odor. If it had been piss, I suspect that the sheet would have served as an effective litmus to test my hypothesis. It struck me that there must have been a different explanation.

I was seemingly respectable again, and Madi leaned in and kissed me for a long time. She had slipped into her now characteristic afterglow, a post-orgasmic state that seemed to be marked by one part effusive joy and another unrestrained idolatry. “I am absolutely the luckiest girl in the whole world!” she oozed with fawning praise. “You are amazing! I thought it couldn’t get any better than last week, but that one was off the charts! I don’t even know how to describe it, but it was incredible, absolutely incredible!”

“Yeah, you mentioned that!” I joked, smiling at her bleakly. I decided I liked teasing her, especially right after she’d cum. The teasing was particularly fun when her face was awash with one of those post-orgasmic blushes that I was coming to recognize as the telltale sign that Madi had had a really powerful climax.

“Don’t tease me! I’m serious! Something just happened there, and it had to do with that toy. When you were pushing on it, it was touching something, and I don’t know what I was doing in response to it, but that was not just another orgasm! It was something entirely different, something way more powerful!”

I thought back to Madi and the salesperson from Downtown Intimates, and I remembered that she hadn’t really told me what the woman had said to her, so I asked. “So what did the lady at the store have to say? What did she tell you about… you know… about anal sex?” I was surprised at myself, but I was a little embarrassed to say the words in front of her.

“It was amazing, John, because that orgasm was exactly like what she was describing to me. She said that when you have something in your anal cavity, it touches a gland of some kind that wouldn’t normally be contacted during conventional sex – I can’t remember what it’s called – but anyway, after your partner stimulates that gland, she said you experience a really intense and very different kind of orgasm.”

“She also said that not all women like having something inside them there, and that’s why she told me to buy the toy before we tried the real thing. She said that if I liked the toy, I would probably like having anal sex with a man.” She looked at me trying to determine whether I was interested in the conversation or not, and she must have decided that I was, because she kept going.

“She actually told me to try the toy by myself when I was alone – to masturbate with it first. I don’t know why, but when we got back from the music, I was just so horny, and so I slipped it inside me when I used the bathroom. I wanted to find out what it would be like if I had regular sex with it in. I didn’t know if you’d notice, but then you went down on me, and it was so fucking pleasurable when you were licking and touching me.”

“But that was only the beginning! When you started pushing in on the thing, oh my god! It was unlike anything I’ve ever felt before! John, now, more than ever, I really want to do this with you!” She had that adamant look on her face like she’d gotten earlier in the afternoon, and I thought for a brief moment that she wanted to start right up again with the anal. I wasn’t quite ready for that.

“Okay, but what did the lady say about lubricants? Did you get some? I thought I saw you buy something besides the toy. Are you supposed to use a special kind of stuff? I mean, something made specifically Escort bayan for anal sex?”

“Well, she said that you have to use a lube no matter what. She said if you don’t use lube, it hurts like hell. Anyway, you’re right, I got some this afternoon; it’s called Astroglide, and it’s just a generic kind of personal lubricant, but apparently a lot of people use it specifically for anal. She recommended it.”

“I used some when I put this in me…” she gestured down as she said it “…and it slid right in, no problem. It seems like it works quite well. Still, that toy felt so weird at first, but, Jesus, when you started moving it, I got used to it real fast, and now I’m really glad that I bought the thing! Besides, it’s pretty, don’t you think?” She lay back and shamelessly exposed both of her orifices to me with the visible knob of that plug still twinkling in her tight, little asshole. I hadn’t noticed until that moment that the glass jewel was pink in color.

I started chuckling. I don’t why, but it struck me as pretty comic that Madi was now so comfortable in my presence that she was not only interested in showcasing her new purchase and commenting on its aesthetics, but was willing to show it to me while it was still stuck deep in her ass! I guess we’d come a long way.

She kept right on going, oblivious to my amusement. For some reason, Madi was on fire, more animated than I’d ever seen her before or since. “The lady also said that I should use the toy right before I put your cock in me. She said it would help me to get ready for you. I told her that you’re really thick, and she said that I probably needed to work my way up by starting with something smaller. Oh, and you were also right about one other thing – she said that it’s best if you prepare for it – that is, if you want to do it right. That’s why I stopped at the pharmacy.”

“For what?” I didn’t understand what she was talking about.

“Well, the lady said that she always gives herself an enema beforehand, so that she’s nice and clean for her boyfriend. She said it makes the whole experience much more pleasant. She said I should take a long, warm, relaxing bath, and then when I’m really at ease, I should use this product I got – it’s called Fleet. It only takes a few minutes, but then afterward she suggested waiting for a little while before we start up. I thought maybe we could do it tomorrow. What do you think?”

“You’ve got this all figured out, don’t you?” I offered her a wry smile, but I wasn’t making fun of her this time. I was actually completely serious. She really had thought of just about everything, and I have to confess, it excited me. I think I was looking forward to it almost as much as she was.

“No, but if we’re going to do it, I want to do it right, and that lady said a lot of people have bad experiences with it the first time, and then they don’t ever do it again. I want to make sure we don’t ruin it for ourselves.” I nodded my understanding.

She paused for a second. “Hey, I almost forgot! Now that I’ve told you what I got; what about you? Are you going to show me your purchase? You said it was for ‘a young lady!’ Could that ‘young lady’ possibly be little ol’ me?” The last three words were delivered in a kind of self-deprecating, faux-Southern accent.

I laughed. “Might be! You think you deserve something?”

She got this fake glum look on her face, like she was hurt. “How come you like to torment me so much?”

I wasn’t trying to be mean, and she knew it, but I apologized anyway. “I’m sorry. You’re right; I probably shouldn’t tease you all the time. It’s right over here.” I got up from the bed, still completely naked, and found the bag on the table. I brought it back over, sat down on the edge of the bed, and handed it to her. “I hope you like this stuff.”

“I’m sure I will!” She smiled and, like a small child on Christmas morning, excitedly opened the bag and pulled out three boxes, two small ones, and another that was a little bigger. Each one contained an item wrapped in tissues. The first box she opened was the stockings. “Ooh, fishnets! You dirty boy; these are really sexy! I can’t wait to wear them!”

She proceeded to open, the bigger box that contained the black, tapestry corset with garters, and finally, the last one – the matching thong. I swear that thong was the tiniest pair of “panties” I’d ever seen. It was, however, just wide enough to cover that little patch of hair she had poking out of her pubic mound, which was now fully on display. “Oh, these are really nice, John! I love them! I especially like the fabric! Very luxurious! Thank you!”

She crawled into my lap and kissed me again, and then all of a sudden, she realized something. There she was with her sexy, pale tits pushed up and out of her bra, wearing those purple silk stockings and the garters, with her nearly bare pussy balanced on my thigh still leaking some kind of fluid and that little, pink plug of hers stuck Bayan Escort in her ass… and then it struck her – I was sitting there without any clothes on with my semi-flaccid cock and loose balls dangling between my legs.

“Oh baby, I am so, so sorry. I’ve completely forgotten about you! After that amazing climax, and then all of the talk about anal sex, I’ve neglected you! Let me take care of you right now!” She ran her hand between my legs and started touching my cock.

I was excited, but I was so turned on by the thought of taking Madi in the ass that I was willing to forego my pleasure until she was ready for the big experiment. “That’s okay, Madi, we can wait if you want to. Maybe we should just go to sleep and then get up early for the real fireworks! I’m really excited to try this with you. You can wear your new outfit! I know the whole thing will be an incredible turn-on for me!”

“But, sweetie, I feel so bad! I’ve been so, so selfish – I don’t care what you say! I’ve cum twice today, and you haven’t had any fun at all!”

“I’ve had fun! I got watch you cum! That’s an awful lot of fun, more fun than almost anything I can think of!”

“More fun than cumming yourself? Come on, John, you know you love it when I take you in my throat. That first time I was deep throating you, I could tell how much you got into it. It wasn’t like you were an unwilling participant. Besides, it won’t take me very long to get you off. ”

I took a quick peek at the clock on the nightstand. It was 1:30 a.m., but that was irrelevant. We both knew she was right – that first time she took me into her throat back at her friend’s apartment, I came faster than I ever had before, and that was when I was trying my hardest not to cum! If I just let her go to town on me, there was no telling how fast she could make me blow my load! Still.

“Are you sure about this, Madi?” Even though I knew she had none, I still had reservations about her gagging and choking on my cock. I had my share of psychological and even ethical issues at the time about how guys treated women. Foremost among them, I regarded misogyny as the male species’ original sin. I knew too many assholes that hated women or at least acted like they did, even though they were all addicted to fucking them. I was trying my damnedest not to turn into one of those assholes.

I had seen plenty of the same sorts of movies that Madi admitted to watching when she was learning to perform that brand of extreme fellatio. And despite the fact that it was something she was convinced all men desperately craved, that shit in the movies never appealed to me. But now it had become a very real part of my own sex life, and I had some ethical questions about it.

It may not have made sense, but I had a tendency to draw a moral equivalency between being on the receiving end of a sexual act that I suspected was, at best, unpleasant and, at worst, humiliating for the author and mistreating and disrespecting women for the mortal sin of not being men.

At the same time, I could not deny that I enjoyed it, and I knew that once I was in the throes of Madi’s earnest ministrations, there was simply no way that I was going to be able to stop, no matter what my conscience told me. I knew it would feel too damn good. I was fully aware that she knew and understood my weakness, and, perhaps even more significantly, that she could use that weakness to get me to do something I wasn’t sure I should do.

“Of course, I’m sure!” she said, hopping off my lap and dropping to her knees next to the bed. Then, she looked up at me with an uninhibited grin, and purring in her honey-coated, sultry voice, she said, “You just sit right there and enjoy yourself, and let me do my thing. I love making you cum!” She clearly understood that at this point there was simply no chance that I would refuse.

This time she started with my balls. They were hanging there so loosely, and so I guess she regarded that as an invitation to take them into her mouth. She sucked and licked them, and then she moved her hand behind them and started massaging the spot between my balls and my ass, pushing upward on it and then flicking her finger against the backside of my scrotum. I think my finger play on her backdoor earlier had somehow inspired her to return the favor.

I was already moaning really loudly when Madi started to lick her way up my shaft. Blood was coursing up my length, and I could feel myself growing by the second. When her tongue touched the sensitive backside of my penis at the point where my shaft, head, and circumcision scar converged, I jerked involuntarily from the sensation. She stayed there for a few moments, alternating between greedy licks using both the flat surface of her tongue and its pointed tip, until she was ready to begin taking me into her mouth.

She started with just the head at first, before she commenced that bobbing up and down that I would come to know as the prequel Escort to an imminent and spirited round of deep throat. Her sexy lips pivoted as she slid up and down my length, opening wider when she dropped down until I could only see their thin, pink exterior formed into a perfect “O” around the thick midpoint of my erection, and then plumping up like pink pillows at the apex of each stroke as her soft, luscious lips puckered around the very tip of my cockhead.

She followed that up with a more varied approach, employing the tag team work of both of her hands, which twisted and slid simultaneously while her warm mouth stroked me with increasing speed. Now, I could see my shaft disappear into the side of her mouth, as her cheek swelled to conform to the shape of my mushroom head and upper shaft. Throughout, more and more saliva bubbled from the corners of her mouth and dripped down my pole on each retreat.

At this point, I had no sense of time, so I don’t know how long it was before she moved on to the grand finale, but when she did, we both knew my seed was not long for my balls.

She was staring up at me with those caramel-colored, doe eyes, and when we made eye contact, she sent me a wordless, but unambiguous signal that she was going for broke. And almost instantaneously, her head dove down, and I felt myself entering her gullet. She could handle perhaps two or three deep penetrations before she started gagging, but then she would come up for air for a few seconds and then resume her work.

Pretty soon, it was like that first time, Madi was moving up and down with incredible speed, taking five or six long stabs from my bloated cock, then gagging and retching for a few seconds, before repeating the process all over again. Her saliva was everywhere, dripping down my shaft and into my pubic hair and all over her pretty face and silky hair.

And then, like that first time, I couldn’t help myself. I grabbed her head with both of my hands, and I started pushing myself into her throat with fierce, penetrating thrusts. The gagging sounds were as loud as my own moans and groans.

And shortly thereafter, I reached the point of no return and announced my intentions, “Ooohhh fuck, baby, I’m cumming! I’m cumming! Where do you want it?” I thought she would ask for it on her tits or maybe on her face, but I soon realized that was not to be the case. Instead, she looked up at me again with the most determined expression on her tear-stained face, and she made it abundantly clear, she was not going to let go.

And then, like that first time, she took me all the way in, and I could feel her tongue lapping at the underside of my balls. That’s when I started discharging ropes of semen into her throat, and she held me there throughout my climax. I could see a half dozen of my convulsive throbs swell her neck, and I knew her lips and tongue could feel my seed pumping out of my balls. I was so far in that Madi had no choice. My jism was already halfway down her throat as it was leaving me, so there was no possibility that she could catch any of it in her mouth. I guess I should have realized that’s exactly what she wanted.

I was grunting like a pig at the trough. It was disgusting. But finally, after I had unloosed eight or nine jets of cum and Madi had matched each with a violent, gagging retch, she had to retreat. I exploded from her gaping maw with a spray of saliva, as she took in one, giant influx of breath that replaced my swollen shaft.

The sight of it all was lurid and shocking, and I couldn’t help but be embarrassed by the whole appalling scene. There was fluid of one kind or another all over poor Madi – tears flowed from her eyes; snot poured from her nose; saliva dripped down her chin and neck; and the last few ineffectual spurts of my semen dribbled onto her breasts. And then there was my cock – it looked as if it was basted in an unholy concoction of bile, semen, and spit. The whole thing was simply too much.

I was still sitting there on the edge of the bed, and Madi was still kneeling between my legs. She tried smiling up at me, but I don’t think she felt happiness. How could she? Instead, she appeared to be in discomfort. I spoke first, probably because she didn’t seem like she could, “No, Madi! Jesus… you didn’t have to do that. That’s… that’s… just… too…” I couldn’t finish my thought. I was too upset to say anything more.

She stared up at me with this incredibly pathetic, needy expression, painted like all the rest of it across her face. It took her a few seconds, but finally she spoke with difficulty. “I… I… wanted to.” The words barely forced a garbled escape from her throat, and I could tell she was still trying hard to swallow normally.

“Why? Why would you want to do that? It can’t be very pleasant for you.” I think she was afraid that I was mad at her.

It was still hard for her talk, but she went slowly, until she managed to push all of the words out. “I wanted… to repay you…, because… you gave me… all those… amazing… orgasms.”

“Madi…” I was incredulous now, but I did soften my tone. “It’s not about repaying me. I don’t need to be repaid. I’m just trying to make you feel good.”

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