Wet Sissys' First Night Out

[spoonchicken]

     In my third year of college I was 20 years old, and sharing an apartment with a roommate. Bob and I had never met before, but he was a fellow student, and he seemed perfectly OK. Not being in the dorms anymore meant I could dress up with an increased level of privacy, but I still had to be careful. It seemed a good idea to keep my "caught red-handed " fantasy exactly that...a fantasy. Thankfully, Bob had never asked about my extra suitcases in the closet. Explaining that would have been awkward , to say the least.                                                                                                                                                                                                                                                                                                               So, one afternoon, Bob informed me that he was going to visit his sister for a few hours, and possibly get some groceries on the way back. I agreed to clean the apartment. As soon as he drove away, I changed clothes, and became Lisa. I wore a shoulder-length brunette wig, a white blouse with a rounded collar, a navy blue sweater, a light blue pleated skirt, white suspenders, stockings, and panties, and a pair of black Mary janes. It felt so good to have the place all to myself for a while. Little did I know...                                                                                                                                                                                                                                                                                                                                       I had gotten everything else done, and was finishing up doing the dishes, when I heard the sound of the front door opening. Instantly I realized that my "caught-in-the-act" fantasy had just become a serious realiity.  My heart literally skipped a beat as I felt frozen in shock and fear. I could only hope it was Bob, and that he was alone. Summoning every last ounce of courage, I slowly turned around and faced him. I couldn't bear to make eye contact with him. He kinda chuckled and said "Wow. how about that!"  I already needed to pee, and the shock of the situation just made things worse. He walked towards me, and gently took my upper arms in his hands. My knees were quivering so badly I could barely stay standing. "So. do you have a girl name?" he asked. "Lisa". My name is Lisa", I stammered out. Bob smiled at me and said "Hello, Lisa...nice to meet you". I couldn't believe it ! Not only was he not freaking out, he was either playing along, or actually interested ! Then, Bob did something totally unexpected. He pulled me towards him, and kissed me. It was just a gentle, closed-mouth kiss, and he immediatly pulled back to see how I'd react. By now my thighs were firmly pressed together, and my knees were about to give out. I gripped his arms, and finally made eye contact with him. Bob stood about three inches taller than me, and he had nice upper-body development. I had to admit he was a hottie.                                                                                                                                                                                                                                                                                                                                                        "Hi Bob...nice to meet you too" I said, as I clung to him. I tried to give him my best sexy "come hither" look with my eyes, but by now my bladder was on the verge of bursting, and I couldn't help but to squirm around. "Are you OK?" he asked. "Yes, but...I just really need to pee" I replied. "Good!" he said, as he moved his hands down lower on my body. With his left hand, he pulled up the front of my skirt, and then gently cupped his right hand on the front of my panties. The only reason my clitty was still semi-soft was because of the feminine feelings that were raging through my body. I gasped as he did so, and almost involuntarily spread my legs out a bit to accomodate him. "Go ahead, Lisa. Be a good gurl, and wet your pants for Daddy". I gripped his arms again as I helplessly let go. My bladder cut loose in a torrential flood of hot piss that very quickly soaked my panties, and began running down both legs. Bobs hand on my panties also helped deflect some of my pee stream towards my inner thighs. I gasped and sighed as I wet myself. Bob moaned as he slowly rubbed his hand back and forth a bit, adding to my excitement. In a firm voice Bob said "Tell Daddy what his little gurl is doing"  I looked him in the eyes, and said in my best little-gurl voice, "Daddy...I'm wetting my pants!"                                                                                                                                                                                                                                                                                                 

[spoonchicken]

     I couldn't stand it anymore. I cupped my hand behind his head and pulled his face towards mine, and kissed him, This was no polite, close-mouthed kiss, either. Our mouths were wide open as we swapped spit and our tongues wrestled with each other.  We stood like that for who know how long, until my pee stream finally began to subside.  I moaned as I bent my knees slightly, lowering myself down on his hand. His left hand was by now on my ass cheek, caressing it in a way I loved. I pulled back from the kiss, and gasped for air. We were both completely hot and bothered by now, and there was no turning back from my sissy destiny. I knew what a gurl was supposed to do. I put my hand on his crotch and felt amazed at how hard his cock was. He smiled and moaned softly as I did so, and I knew exactly what to do next. Keeping eye contact with him, and smiling the entire time, I slowly lowered myself down to my knees. Sadly, it had been a few years since my last encounter, but  I still remember how. I unbuckled his belt, unzipped his fly, and pulled his pants down to his ankles. To my great surprise, Bob was also wearing stockings, panties, and a suspender belt !  Even more of a surprise was the fact that they were my garments ! I looked up in surprise and shock, with the obvious question on my face. Bob just grinned even wider and said "You're not the only one who likes to play dress-up sometimes. I picked the lock on your suitcases when I found a pair of panties under the bed. You've got some cute stuff !"  I couldn't help but laugh, as I took his rock-hard cock in my hands. I took it all the way into my mouth once just to  wet it, and then pulled back and began softly blowing on it. It got even harder as I did that. Bob groaned at that, and I knew he was all mine. I ran my tongue around the edges of his cockhead, driving him crazy. His hips bucked slightly and I knew it was time. I took his cock into my sissy mouth, and began giving him the most memorable blowjob in history. I pulled back and gasped out " My God, Daddy. Your cock is so big I can barely manage it !" Bob responded by grabbing my hair with one hand, and forcing his cock back into my sissy mouth. "Do your best, baby!" Bob said. I cheerfully did my best to obey my Daddy !                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                       As I continued to suck Bobs cock, an unexpected feeling arose within me. At first I wasn't sure what it was. Then I realized that strangely enough, I needed to pee again.   I could have simply let go, but I wanted to maximize the situation for us both. I had been moaning with pleasure the entire time, but now it grew louder as I began doing the potty-dance while down  on my knees. Bob noticed this and asked " Lisa, do you need to pee again ?!?"    I tried to say yes , but with a mouthful of hard cock, it sounded more like a sexual gurgle. As my bladder cut loose again, I pulled back and cried out" OH, Daddy...I'm wetting my pants again !" Immediately I plunged his cock back into my mouth. I couldn't believe all this was happening....getting caught red-handed all dressed up by my cute roommate, his interests, and now I was wetting myself while giving him head. I felt like such a total sissy I actually began crying slightly with joy and pleasure. My satin panties were still drenched from the first wetting, so my pee just streamed down both legs into the growing puddle on the kitchen floor. It felt like sissy heaven to me! Bobs hips bucked violently back and forth. He was just as turned on by my wetting as I was. My arousal levels were at an all-time high, and as soon as I stopped peeing, I had the most insane sissy-orgasm imagineable. I screamed as I came " Daddy I'm cumming !" My jism  exploded inside my pee-soaked panties as I felt Bobs cock start flexing, Instantly I pulled back, and was rewarded with Bob shooting his hot load all over my sissy face, He came in two or three powerful bursts of cum, completely splattering my cheeks and forehead. As we both sighed contently, I used his still-hard cock to smear his jism all over my face, smiling at him, and licking his cock clean as I did so.  I had never felt so vindicated as a sissy then at that moment in time. Bob gently hoisted me up to my feet, and hugged me close. Both his hands were on my ass as he said "Let's get cleaned up. We don't want to be late for the party tonight. And you're gonna be my date tonight".  I told him I'd never gone out in public when dressed up, but he just said "First time for everything"  I gulped at that. This was really shaping up to be a memorable evening ! 

[spoonchicken]

     Hmmm...first time in public, and at a party where I would know everyone, and they would know me ? My anxiety was at an all-time high, but this was exactly what I'd always dreamed about as a sissy. To find a cute guy who was reasonable straight to be Lisas boyfriend. To find someone who enjoyed pee games as much as I did. To go out in public on a date and see what happened. There was no turning back, and I didn't want to. But for something like this, I decided to dress to kill. After cleaning up, I changed into a new outfit. I swapped out the wet stockings and suspender belt for dry fresh items. But instead of panties, I decided to see how far I could go with Bob on the watersports aspect. So instead of panties, I opted to wear a diaper. A nice pink disposable with matching pink plastic panties. On top of that went my black leather miniskirt and 3" white high heels. Add to that a long-sleeved white satiny blouse, and I was all set. It was a warm night out, so there was no need for a coat or jacket. I walked out of my bedroom and displayed myself for Bob. His eyes bulged slightly as he smiled and said " Wow, Lisa....that is just a super-cute look!" I smiled from ear to ear as I thanked him. Bob had changed from tennis shoes to his cowboy boots, so in spite of my heels, he was still a bit taller than me.  I took his arm as we walked toward the door. We stopped and looked at ourselves in the hallway mirror, and I had to think we made a cute couple! Bob cupped my chin in his hand as he kissed me, and asked if I was ready for this. I replied by gently squeezing his cock inside his pants and smiling up at him. But when he opened the door and we stepped outside, I hesitated on the front porch. In spite of how much I wanted to do this, I couldn't help feeling nervous. Add to that the fact that I knew I'd have to pee again soon, and we hadn't even arrived at the party yet!                                                                                                                                                                                                                                                                                                              As we drove to the party I was overcome by intense feelings of  sissy. I literally couldn't help myself but to play with Bobs cock as we were driving. He grinned and asked me to be careful. I just giggled at that, as I pulled his cock out and began blowing him while we were driving. He shivered as I sucked him, and i felt his right hand going up my skirt. I spread my legs as best could for him, wondering how he'd react to my diaper. I moaned loudly as his hand touched my diapered crotch. He laughed and said " A diaper? Reaaly? Cool!" I figured now was as good a time as any, so as his hand was cupping my diapered crotch, I began to wet. I whispered to him "Daddy? I'm wetting my diaper!" as his hand felt my wetness.  Bobs whole body jerked at that realization, and I could feel his cock reacting as well.  We needed to keep clean , so I had no choice but to swallow his hot load this time. As he came, he took his hand off my diaper, and began shifting gears. With a shock, I realized that we had arrived at the party, and the valet parking guy was standing there watching us with a grin on his face ! My face grew bright red at the embarrasement, but Bob just tucked his cock back into his pants and smiled at the valet. "Eveing, bro! How you doing?" Bob asked. "Fine, sir, just fine" the gut replied. Bob stepped out, took the ticket, and walked around to open the door for me, I stepped out of the car and thought to myself "Here we go, gurl"...

[spoonchicken]

   I took Bobs arm as we entered the building. It was a large college party, with lots of people and the usual DJ spinning songs. We stopped first at the bar and both got drinks. A few of Bobs friends were there, and came over to say hi. Bob introduced me , and all the guys were nice. I could also feel them undressing me with their eyes, and very much enjoyed the feeling! If they only knew! Quite a few of my friends were there too, and just as I was wondering what would happen, several of them also came to the bar. As they all got fresh drinks, Bob introduced me as Lisa. We shook hands, and one guy even kissed my hand ! Bob & I both chuckled at that. Not one of my friends recognized me when I was in drag. I couldn't believe it ! Not one ! I was in seventh heaven at that. When they left us, I breathed a deep sigh of relief. Bob noticed, and smiling as he said it, told me I made a really supercute hot chick. I thanked him and smiled, and actually began to relax a bit. This was seeming to work OK. Not only was I was passing well in public, but my own friends didn't even recognize me! This was great! We made our way to a table with several of our friends and sat down. I crossed my legs like a lady, and hoped the bulk of the diaper didn't give itself away. After a bit of time drinking and chatting, Bob and I decided to play pool. We got a table. As I broke, I leaned over a bit as a tease, wondering how many sets of eyes were focused on my ass. If only they knew there was a clitty inside a diaper underneath my black leather skirt ! Bob saw that I was being a bit of a cocktease, and whispered in my ear " If you keep that up, you'll get a spanking for sure when we get home". I just giggled and replied " I certainly hope so, Daddy!" By now the booze was starting to hit me, and I had to wet again as we played pool. I stood there with my pool cue in hand, imagining it was Bobs cock in my hand as I began wetting my diaper a second time. It was a large pee, and by now my diaper was thoroughly soaked. Somehow , Bob knew what I was doing, and smiled at me across the pool table as he sunk the 8-ball. I was positively giddy and light-headed. and told Bob I needed some fresh air. We stepped out the back where a bonfire a burning merrily away, and the music wasn't as loud. I felt Bobs hand on my ass as we stood there, and knew I had to have him inside me very soon. My sissy urges were surging out of control. I pushed my butt up against Bobs pants, and felt his cock against my cheeks. Finishing his drink, Bob put both his hands on my hips and pulled me back against him. It  felt like I was giving him a lap-dance while standing up. His now rock-hard cock pressed up against me as I softly moaned in pleasure.                                                                                                                                                                                                                                                                                                                                                                           Wouldn't you know that was when one of Bobs friends walked up to us. Bob introduced me to his former roommate Dave. Bob was a baseball player, and had the male body for it. Dave, however, was a football player, and he was built like one. His biceps were huge, and his chest was so broad and wide I wondered if he bench-pressed small cars as part of his workout routine. After Dave walked away looking for a drink, I whispered to Bob "Don't take this the wrong way, Daddy, but I'd really love to blow that guy". Bob actually laughed and said "only if it's a threesome with me fucking you as you suck him!" I smiled at the thought of that, and said "OK!" Bob realized I was serious, and a strange smirk came across his face. "OK. let's go ask him!"

[spoonchicken]

   Five minutes later , the three of us were in a storage room down a side hallway. By now I was so horny I would have let the entire varsity squad bang me all night long. I dropped to my knees as Dave grabbed my hair, and forced his cock into my sissy-slut mouth with no protests from me. His cock was huge, long and wide. It was a real struggle to get it into my mouth, but I did it. As Dave was fucking my face remorselessly, I felt Bob grab my thighs just above my knees and pull my ass back a bit. He slowly pulled my skirt up to my waist, and I shivered with joy knowing what was about to happen. Carefully, Bob pulled my pink plastic pants down my legs to just above my knees, and gently tore a hole in the back of my piss-soaked pink diaper. I heard him dropping his pants, and then felt his cock on my leg. He teased me by rubbing his stiffy up and down my thighs, asking me if I was ready for it. With a mouthful of cock I couldn't answer, but I didn't need to ! I felt  the tip of his cock poised at my hole, and then Bob slowly entered me. Finally! My moment of sissy truth had arrived! The last few shreds of my masculinity abandoned me as Bobs cock slid into my sissy fuck-hole. I groaned with pleasure as I felt Bobs cock inside me for the first time. I felt so good I couldn't believe it. Bob fucked me slowly at first, but then began picking up the tempo as I rocked my ass back against his body. Daves cock was still in my mouth as Bob fucked me, and I never thought a sissy could be so lucky as this ! With a mighty final thrust into my mouth, Dave came inside me. His cock was so big, and his load so fat, that his jism was dribbling out the corners of my mouth as he came. I pulled his cock out of my mouth and smeared his cock all over my face. Dave smirked at me as he zipped himself up. "Damn, dude, your old lady gives a mean blowjob! Thanks, bro!" Dave said, as he exited the room. Now it was just me and Bob. By now Bob was ruthlessly pounding me with his cock. Every time he thrust foward and compressed my diaper, a small squirt of pee would run down both of my legs. I moaned and screamed like the slut I was, begging Bob to fuck my dirty, filthy sissy slut fuck hole. As I talked dirty to him, his cock got even harder and his tempo increased. The waves of feminine sissy pleasure flooding my body were indescribable. This was exactly what I'd always dreamed of ! Finally, Bob and I could both take no more. Bobs moaning and groaning transistioned to a sustained gutteral sound as he came inside me. The feeling of his hot jism shooting inside me was too much, and I began to cum as well. Tears of pleasure and joy were running down my face as we both climaxed violently together. Just as before, as soon as I was done cumming, my bladder let go, and I wet my already soaked diaper a third time. This time, the diaper was too saturated to hold much more, and a lot of my pee simply  gushed down my legs. Some of it pooled up in my plastic pants, but most of it ended up on the floor. Right then Bob finished cumming, and began to piss inside me ! I shivered and screamed at the feeling of receieving a piss enema from my lover. My ass was  filled with Bobs cum and pee, and as soon as he pulled out,  it all came rushing out of me. Piss mixed with jism splattered the floor as we both gasped with delight. By now I was a total mess. My face was still covered with Daves cum, my legs and stockings were soaked with piss, and my fuckhole had been stretched to the limit. It was wonderful. Bob and I stood up and put ourselves back together as best we could. I decided to not clean my face. I wanted the whole world to see what a slut I was, walking around in public with cum all over my face ! I asked Bob if we were done for the night, and he laughed. "Hardly! Now let's go home and finish what we've started ! " We kissed again, and holding hands like teenagers, went in search of the parking valet guy so we could leave. The expression on his face was priceless as he looked at me. I just got into the car, let Bob shut the door, and hiked my skirt up as high as I could. The parking valet guy smiled and winked at me as Bob said "Don't cocktease the poor kid, honey! He's gonna have blue-balls all night long now!  

[smarti]

It's good writing! To be brutally honest, the content is not my bag exactly. For some reason, I'm not much turned on by the sexual act itself, but I find the story very readable. I'm sure there's an audience for it, and it benefits with the energy from the liberation of your feelings. Technically, my main advice would be to split it into paragraphs for ease of reading. A few minor tweaks to punctuation. "guttural".. 

"I moaned and screamed like the slut I was, begging Bob to fuck my dirty, filthy sissy slut fuck hole." Both a great line, and a bit of a tongue twister

take care x

 

 

[spoonchicken]

Thanks for the feedback ! I wondered about it. Good  entertainment must have both an interesting story, and also clever story-telling. I felt like it was "pretty good:, but that's not up to me ( or any other writer ) to say, is it ?  So I was curious to get the opinions of someone whose judgement I'm inclined to trust.  

I did try to break it down into paragraphs as best I could...guess I could have done a bit better there...

And I didn't proofread it...after thinking & typing for almost 2 hours, I was done ! lol 

So...I guess I've lost my cheery as a writer 

[jesse78]

On 4/17/2021 at 5:41 PM, spoonchicken said:

   I took Bobs arm as we entered the building. It was a large college party, with lots of people and the usual DJ spinning songs. We stopped first at the bar and both got drinks. A few of Bobs friends were there, and came over to say hi. Bob introduced me , and all the guys were nice. I could also feel them undressing me with their eyes, and very much enjoyed the feeling! If they only knew! Quite a few of my friends were there too, and just as I was wondering what would happen, several of them also came to the bar. As they all got fresh drinks, Bob introduced me as Lisa. We shook hands, and one guy even kissed my hand ! Bob & I both chuckled at that. Not one of my friends recognized me when I was in drag. I couldn't believe it ! Not one ! I was in seventh heaven at that. When they left us, I breathed a deep sigh of relief. Bob noticed, and smiling as he said it, told me I made a really supercute hot chick. I thanked him and smiled, and actually began to relax a bit. This was seeming to work OK. Not only was I was passing well in public, but my own friends didn't even recognize me! This was great! We made our way to a table with several of our friends and sat down. I crossed my legs like a lady, and hoped the bulk of the diaper didn't give itself away. After a bit of time drinking and chatting, Bob and I decided to play pool. We got a table. As I broke, I leaned over a bit as a tease, wondering how many sets of eyes were focused on my ass. If only they knew there was a clitty inside a diaper underneath my black leather skirt ! Bob saw that I was being a bit of a cocktease, and whispered in my ear " If you keep that up, you'll get a spanking for sure when we get home". I just giggled and replied " I certainly hope so, Daddy!" By now the booze was starting to hit me, and I had to wet again as we played pool. I stood there with my pool cue in hand, imagining it was Bobs cock in my hand as I began wetting my diaper a second time. It was a large pee, and by now my diaper was thoroughly soaked. Somehow , Bob knew what I was doing, and smiled at me across the pool table as he sunk the 8-ball. I was positively giddy and light-headed. and told Bob I needed some fresh air. We stepped out the back where a bonfire a burning merrily away, and the music wasn't as loud. I felt Bobs hand on my ass as we stood there, and knew I had to have him inside me very soon. My sissy urges were surging out of control. I pushed my butt up against Bobs pants, and felt his cock against my cheeks. Finishing his drink, Bob put both his hands on my hips and pulled me back against him. It  felt like I was giving him a lap-dance while standing up. His now rock-hard cock pressed up against me as I softly moaned in pleasure.                                                                                                                                                                                                                                                                                                                                                                           Wouldn't you know that was when one of Bobs friends walked up to us. Bob introduced me to his former roommate Dave. Bob was a baseball player, and had the male body for it. Dave, however, was a football player, and he was built like one. His biceps were huge, and his chest was so broad and wide I wondered if he bench-pressed small cars as part of his workout routine. After Dave walked away looking for a drink, I whispered to Bob "Don't take this the wrong way, Daddy, but I'd really love to blow that guy". Bob actually laughed and said "only if it's a threesome with me fucking you as you suck him!" I smiled at the thought of that, and said "OK!" Bob realized I was serious, and a strange smirk came across his face. "OK. let's go ask him!"

Love where this is going

On 4/17/2021 at 5:41 PM, spoonchicken said:

   I took Bobs arm as we entered the building. It was a large college party, with lots of people and the usual DJ spinning songs. We stopped first at the bar and both got drinks. A few of Bobs friends were there, and came over to say hi. Bob introduced me , and all the guys were nice. I could also feel them undressing me with their eyes, and very much enjoyed the feeling! If they only knew! Quite a few of my friends were there too, and just as I was wondering what would happen, several of them also came to the bar. As they all got fresh drinks, Bob introduced me as Lisa. We shook hands, and one guy even kissed my hand ! Bob & I both chuckled at that. Not one of my friends recognized me when I was in drag. I couldn't believe it ! Not one ! I was in seventh heaven at that. When they left us, I breathed a deep sigh of relief. Bob noticed, and smiling as he said it, told me I made a really supercute hot chick. I thanked him and smiled, and actually began to relax a bit. This was seeming to work OK. Not only was I was passing well in public, but my own friends didn't even recognize me! This was great! We made our way to a table with several of our friends and sat down. I crossed my legs like a lady, and hoped the bulk of the diaper didn't give itself away. After a bit of time drinking and chatting, Bob and I decided to play pool. We got a table. As I broke, I leaned over a bit as a tease, wondering how many sets of eyes were focused on my ass. If only they knew there was a clitty inside a diaper underneath my black leather skirt ! Bob saw that I was being a bit of a cocktease, and whispered in my ear " If you keep that up, you'll get a spanking for sure when we get home". I just giggled and replied " I certainly hope so, Daddy!" By now the booze was starting to hit me, and I had to wet again as we played pool. I stood there with my pool cue in hand, imagining it was Bobs cock in my hand as I began wetting my diaper a second time. It was a large pee, and by now my diaper was thoroughly soaked. Somehow , Bob knew what I was doing, and smiled at me across the pool table as he sunk the 8-ball. I was positively giddy and light-headed. and told Bob I needed some fresh air. We stepped out the back where a bonfire a burning merrily away, and the music wasn't as loud. I felt Bobs hand on my ass as we stood there, and knew I had to have him inside me very soon. My sissy urges were surging out of control. I pushed my butt up against Bobs pants, and felt his cock against my cheeks. Finishing his drink, Bob put both his hands on my hips and pulled me back against him. It  felt like I was giving him a lap-dance while standing up. His now rock-hard cock pressed up against me as I softly moaned in pleasure.                                                                                                                                                                                                                                                                                                                                                                           Wouldn't you know that was when one of Bobs friends walked up to us. Bob introduced me to his former roommate Dave. Bob was a baseball player, and had the male body for it. Dave, however, was a football player, and he was built like one. His biceps were huge, and his chest was so broad and wide I wondered if he bench-pressed small cars as part of his workout routine. After Dave walked away looking for a drink, I whispered to Bob "Don't take this the wrong way, Daddy, but I'd really love to blow that guy". Bob actually laughed and said "only if it's a threesome with me fucking you as you suck him!" I smiled at the thought of that, and said "OK!" Bob realized I was serious, and a strange smirk came across his face. "OK. let's go ask him!"

Love where this is going 

[Transfusionelle]

Spoony I really dont know what to say. I thought I was the only one that loved to party this way back in college. Very good reading material !! I love the part with Bob holding you while your peeing and kissing. Believe it or not that is one of the best things I love about wearing a diaper and kissing Eve. She loves to feel the warm pee as I fill the diaper up and kiss her. Eve had left me a post it on the monitor and I just read it now as I am putting on my diaper and getting ready to play with myself before falling into a nice slumber. Once again very well written, That story brings back so many fond memories.

[spoonchicken]

Thx Elle 

[chefke]

Wow nice story, hope to see you write more?

[jesse78]

Wonderful story, keep up with the writing

[diappernsfwboy]

hey can I be in the story