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Unexpected Pleasures

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Unexpected Pleasures

I woke up to the familiar sensation of Stephanie's hand sliding up and down on my hard-on. She's a morning sex person and has always taken advantage of my "pee-hard on". "Mmmm..." was all I could mutter and with that, she knew I was awake. She pulls my shorts off and lies down on top. Kissing me gently as she continues to pump with her left hand, she says "I see you're up already as usual" in her sweet sarcastic tone. "We can't let that go to waste!" She mounts me and starts sensuously sliding my dick in and out of her wet pussy.

"You better finish up soon babe, my bladder feels like a water balloon ready to explode with your weight on it." I whispered. "Two more honey...ugh!...mmm...oh! Oh! UGH!"

She loves taking me this way. She always said that there's nothing like taking an erection that isn't dedicated to anyone and making it hers. I guess I could say that I understand what she means. Men do it to women all the time. We get an erection and we want to put it in a woman, she gets wet and wants a man in her pussy.

"Uuuughhhhhh!" she whimpers, I feel the beads of sweat that formed on her lower back. "Thanks babe..." she whispers in my ear and slides down beside me. I run to the bathroom and struggle to let out what felt like a gallon of urine that has accumulated in my bladder through the night. Let me tell you, it isn't easy when your erection is pointing up and you have to aim your stream into the toilet which at that time seems like very small target. Having to point your "pee-er" down makes the act quite painful sometimes and I've resorted to just standing next to the tub and letting it hit the shower stall wall. She makes fun of me whenever I do this, she yells out "Hahaha, are you being a stud again and marking the shower wall?" to which I would respond, "Better the shower wall than mark your pussy from the inside hon!" I say it as a joke but I've always wondered about doing that. I mean what harm can it really be? Aside from the extra salt, urine is sterile so it would be more like a vaginal douche. I can't deny the fact that I've tried on some occasions but it never really happened. I read it has something to do with all the detours in the male plumbing during erection to make way for the passage of semen and sperms.

I climb into the tub and proceed to take my morning shower. It rinses the wall of urine as well so my routine serves two purposes on mornings like these.

I step out of the bathroom and there she is, all dresses up for work. Modest and innocent looking. I've always said that if I didn't know any better, I would have thought she was a virgin. She got me to really believe that the women who look very innocent and tame actually have tigers in them waiting to pounce on unsuspecting men.

Naturally, not having cum yet, my dick is at full attention. I try to take her clothes off but she resists and sweetly says "You know I can't go to work with your cum in my pussy, it keeps draining out of me the whole day and I spend a lot of time pointing fingers at my friends as the source of the aroma" with a laugh. "Tonight?" she asks with her head quickly nodding up and down.

On days when I wouldn't let her off that easy, she resorts to sucking me off and swallowing every drop of cum. After which she heads off to Starbucks for her usual morning latte which washes the smell form her mouth.

She has told me about a time that I finished up inside her before work. Her friend Sarah came to her desk and just blurted out, "It smells like one of the guys just jacked off in here" with a laugh. She responded with "Well, that weird smell seemed to have gotten stronger when you came in, what is that?" Looking innocent does have its advantages, one of them being that with issues like this, her friends tend to look at her as a non-guilty party all the time.

Sarah ends up confessing that she had sex the night before but since she showers every morning, you would think that the smell was gone by the time she gets to work. Stephanie just laughed as if she knew nothing. Sarah walked away puzzled, probably trying to figure if she should start douching! Hahaha!

I came home late that evening, tired. I walked through the door and there she was in the living room watching TV. As usual, only in her Victoria Secret panties. Gave her a kiss and headed straight for the shower. Dried off and went to bed. I fell asleep really quick.

It must have been 4 AM when I woke up. Just in time to catch Stephanie turning to grab my dick. She started pumping and sucked me for a few minutes. My bladder didn't feel too full that time so it felt a lot more pleasurable than usual. I was horny! So she mounts me and I let her have one orgasm. Then, a crazy thought crossed my mind. I wiggled to get on top. She resisted at first but gave in. I pumped her hard and she had a screaming orgasm. She didn't like those. She said it took too much of her energy and she struggled at work to stay focused. Well today was going to be one of those days. She came screaming once more and told her I was ready to come. She tried to pull me out "Hon, you know I don't like smelling like cum at work, let me suck you dry." I know a lot of men would turn over in a heartbeat and give in to this request but since I've had that regularly, it feels more ordinary to me now. When I'm really horny, I crave to pump my load in her pussy.

"What if I wash it out for you?" I said, "What do you mean?" she responded. Without saying anything else, my dick still inside her, I carried her to the bathroom and set her down on the sink. She got hornier from not knowing what I was planning to do so she was very cooperative. I began pumping her hard again. She came screaming within a few minutes. Then, it was my turn. I told her I was cumming. She opened her legs even wider and leaned back a bit knowing that I love plunging it to the hilt when I cum. She had another orgasm as I was having mine. I adjusted her position to where her pussy was hanging over the edge of the sink. I relaxed a little bit and slowly, was able to release a stream of urine into her pussy. Once I got the stream started, that was it. It wasn't going to stop. Her eyes opened wide and she started screaming and grabbing, almost convulsing. My stream got stronger and I could feel her pussy filling with urine. I squeezed my bladder to create even more pressure. My urine started dripping and flowing out of her pussy into the sink. She orgasmed for about 2 minutes as I let my bladder completely empty into her pussy. I pulled out and more urine washed out, led her to the shower and we showered together. She was tired, but very happy. She confessed that it was the biggest and longest orgasm she has ever had in her life. She described the sensation to me as we were washing up. "My pussy felt warm, then hot!" she said. It was nothing like anything she had ever experienced before. After her pussy filled up, she felt like she was being stretched by something really big and hot the whole time. She was coming that whole time too. She also admitted to peeing as she came just intensified her orgasm even more.

We were so turned on by talking about what just happened that we started making out in the shower. She started sucking my dick and it was coming back to life. We kissed some more and she said "So... do you have any more surprises for me? Today's the day to break them out because I'm calling in sick. There's just no way I can function at work after that one, hahahaha!" I kiddingly answered "If you're up to it, I have another surprise but it would require you to empty your bowels. She knowingly smiled. Stepped out of the shower and told me to keep that thought. She dried up and left for the other bathroom. Five minutes later, she came back into the shower.

I asked her if she was really up for an adventure. "What do you think? As long as you promise you won't hurt me" was her reply.

She was never a fan of anal sex, judging from all the accounts of former boyfriends inquiring and her shooting them down with "You are not touching that!" I remember her saying it to me too and it was never discussed again.

This morning was different though. She was horny. She was willing. Probably curious as to what else she's missing out on stemming from the experience earlier. Water sports have always grossed her out and she said she never understood what pleasure those "wierdos" derive from it. I guess now she does!

So back in the shower, I got the soap and washed both her holes. Then I grabbed the KY, squeezed some onto my fingers and proceeded to finger her ass while we kissed. I let the stream of water wash my over my fingers and repeated the process a few more times. When I was confident I cleaned her anal track pretty good. I asked her get on her hands and knees and licked her ass under the streaming shower. I inserted two fingers in her pussy and made her come again. Her pussy felt different that time. I could feel the ripples very distinctly. My curiosity got the better of me so I slid my dick in. Wow! Talk about a new sensation. I could feel the ridges on my penis as I glided in and out. I had to stop myself and pull out to keep from cumming. I grabbed the lube and squeezed a generous amount on my fingers. This time I slowly eased two fingers in her ass, she seemed a little uncomfortable at first but after a few seconds, her moans of pleasure returned. "Time to go to bed" I said and we got out of the shower. We dried up and kissed our way to the bedroom. I laid her down on the bed and opened her legs. I went straight for her clit. I licked and sucked it with re-ignited passion until she came again. I pushed my index and middle finger into her pussy, she was soaking wet and they went right in. As I licked her clit, I pulled my fingers out and gently reinserted them into her ass, shortly followed by putting my thumb into her pussy. She loved it. "Please don't stop....don't you dare stop!" I kneaded the wall between her pussy and her rectum and made her come again. I got up and placed my dick inside her pussy. Oh that sensation was unforgettable. The ridges! Yes the ridges were so defined! After a few minutes of this, again I told her I was ready to come. "But I don't want to make a mess in that cleaned out pussy of yours" I said. With that I got a pillow and placed it under her butt. Her spread legs went naturally higher giving me better access to her anus. I slowly nudged the head of my dick at the opening of her anus. I whispered into her ear "Babe, I'm going to take your anal virginity" I felt she wanted to resist but wasn't showing it. Her eyes opened wide and shut tight as I slowly eased the head past the opening, then she smiled and said "After the initial penetration, it actually feels good!" So I slowly worked up a pace going faster and deeper with every pump. When I got balls deep into her ass, I was ready to come. She was moaning too. With a hard thrust I pushed in and started squirting into her rectum. She thrashed and came with me!

It was almost 11 AM and I had to call in sick too! Which I did, while still in her ass. We kissed until we drifted to sleep. It was about 2 PM when I woke up. Her sphincter had held my dick in place and it appears that we really didn't move while we were asleep. In fact, we were stuck together. I tried to pull out but she said it was too painful. My dick was soft but since it was trapped inside, the head and part of the shaft that was past the opening had collected blood and swollen inside her. I was scared for a while with the thought of having to call 911 for something like this.

The panic actually started to make my dick hard again, I guess it was the pervert in me. So I pulled my dick as far as I could it without giving her any discomfort. I squeezed a lot of lubricant on the shaft and started to pump in and out of her to get the lube into her anal track. She started moaning in pleasure again. I grabbed the vibrator that she keeps in her night stand and pushed it into her pussy. She orgasmed! I came again and this time, I was able to pull my dick out. My penis looked like a light bulb! The portion that got trapped was about twice the girth it would normally be. We laughed at what happened and drifted off to sleep in each others arms again.

I don't know what time it was when I got up but the sun had already set. Stephanie wasn't beside me so I got up, a bit disoriented and found her in the kitchen. She had dinner ready and signaled me to grab a chair. We ate dinner and joked about the-would have been emergency call. It was easier to laugh at it then than it was during the crisis. "Funny" she said, "I feel like I've sexually matured five years experience-wise in the past 24 hours. Thanks for letting me know what I was missing" After dinner, we sat in front of the TV and cuddled. I asked her if she was ok. She said she felt fine. Except that she had a little diarrhea which woke her up from the sleep. She laughed and said she had to go twice before it felt normal again. We went to bed and fell asleep with me spooning her.

I woke up with a hard on the following morning. My dick was still a little swollen so it was bigger than it's ever been. Stephanie was sleeping face down, naked as usual so I got on top of her and slowly pushed it into her pussy. It woke her up and I said "My turn to wake you up with sex!" She said it felt big. Like I was someone else. I told her to close her eyes and to go ahead fantasize about whoever she wants, she was facing the other way anyway. We came at the same time. After cuddling for a few more minutes, we both got up to get ready for work. On her way out, she gave me a kiss and said "We have to this again...on a weekend next time!"

Turns out she really enjoyed anal sex she wanted it to be a regular part of our plays. Just not the getting stuck part. She also started asking me about how confident I was about our relationship. She really liked the double penetration with the vibrator and said she can just imagine how good it would feel with 2 real dicks inside her at the same time. I just told her maybe, one of these days, maybe.

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