(a bit exgaggerated, though most of the parts regarding my girlfriend are fairly true though made to fit the storyline)
Well to start things off I will give a little background information about myself. I realized I was a sissy when I was dating my first girlfriend, Jennifer. I was 14 and she was 13. Like most young teens we were filled with raging hormones and eager to jump on one another. After months of fooling around the big day came when we finally had sex. We were both virgins so saying that it was not earth shattering is an understatement.
It was mid summer and I had snuck over to her house while her mom was away at work (her parents were divorced and it was just her, her mother and her baby sister). Jennifer stripped down to her panties and I my boxers. We fooled around till I worked up the courage to make my move. I finally did and we stripped out of our underwear and I attempted to insert myself into her. I felt her warmth and began humping like mad. She asked me if I was inside yet, and I replied with a timid 'I think so.' I can tell you, as a young boy this was not something I wanted to hear.
I only lasted 30 seconds or so, but during the time she never felt me (mind you she was a virgin). When I rolled off of her, I was surprised to see that not a drop of my cum was inside her, instead it was just below her nether region. When she pulled her panties back up there was only enough cum to make a small spot on the crouch of her panties, maybe the size of a silver dollar (at fourteen my penis was an inch fully erect and almost looked like a clit when not).
Jennifer examined herself then looked down at my privates. She laughed and said, "Wow, you look like me." To prove her point she pulled the crouch of her panties to the side and pointed out the similarites between her clit and my now spent penis. She finished up with a "but I still love you sweetie."
When I went to grab my boxers she stopped me. "Wait, I got something that will look really cute on you." She went to her dresser and rumaged through her intimates. Finally, she pulled out a well worn pair of Disney Princess panties. "Here, I have not worn these in a while. Put them on."
Looking back you would think that I would have refused, or protested, or anything. But the way she had compared me to herself had left me feeling like a little girl. So I took them and slid them on. They were white with pink trim, and had a picture of Cindrella on the front. The panties were a bit tight and pressed against what little manhood I had. To my surprise the panties made me look like I had a cameltoe and the bit of cum left on my penis began to soak through.
Jennifer smiled and said 'see we match.' She threw my boxers away and I went home that way. For the next few days I wore the panties she had given me all the time. Living with my mom I of course could not wash them so I hide them in my room.
Over the next few months I continued to sneak over to Jennifer's. She added to my panty collection. When we "had sex" she did not take off her panties. She said it was a waste of time since I could not get inside her. So I would hump her while she wore her panties till I came.
As this continued it became harder and harder for me to hide my panties from my mom. I had ten pairs. To make matters worse Jennifer had made me shave what little hair I had from the neck down. I was out playing with my friends on a Saturday afternoon when I heard my mom calling from the porch. It was getting late, sometime after 6, so I was not surprised she was calling. As I walked in we made small chat for a few moments till she told me to wash my hands before dinner. As I was walking she said, almost as an afterthought, 'Oh and grab that basket of laundry by the table. I washed some of your clothes.'
I walked over and grabbed the basket. I did not give it a thought was my panties were what I thought was well hiding in my room. When I got to my room I grabbed the shirts that were on top and started to put them away. To my horror, nine pairs of panties were neatly folded beneath them (I was wearing the tenth, it had been sometime since I had worn anything else). I heard my mother from my doorway, 'care to explain?'
I was in shock. I began to lie and say they were Jennifer's but my mom cut me off. 'Are you wearing a pair now' she asked, her voice neutral which scared me more than if she had yelled. I simply nodded. 'Well let me see.' Again she said it very calmly, but her look made he dare not argue. I removed my pants. She looked at my shaved legs. My T-Shirt hung low enough to hide most of the panty but the crouch was visible. 'And you shirt.'
I did as she commanded. She could now see that I was wearing a pair of pink panties with the word "Princess" printed across the front in white lettering (Jennifer had only giving me girlie girl panties). Again the panties were tight and they made it look like I had a clit. 'Well you certainly look like a princess'.
She pressed me for an explaination and exposed as I was I broke down and told her the entire story. She only nodded and once I was done, allowed me to put my shirt on and come to dinner. For the rest of the night I walked around the house in only a T-Shirt and panties.
The next day my mom left for the day. She did her grocery shopping, hair appointments, ect. on Sundays. Jennifer and I had already arranged to have her take a bus to a bus stop just a few blocks from my house for some fun. I meet her there and we embraced. Despite the her dressing me in panties, we were still boyfriend and girlfriend.
When we were half way home a break appeared in the conversation and I began to tail her of my misfortune the night before.
'My mom found my panties.' I said this while looking at the road ahead of me. It was still a bit embrassing to talk to her about my panties, though she always made sure we did. She looked at me half shocked and with a bit of a smile of her face. 'What?! She found them? What happened?' I replied still looking at the ground, 'she washed them and put them in my laundry basket. She even made me take my pants and shirt off.'
'She saw you in your panties' she exclaimed. 'Keep your voice down,' I replied, though noone was on the street. 'I had to go the whole night in nothing but my T-Shirt and panties.' 'Which ones were you wearing?' she asked, her smile and excitement were clear on her face. I could tell that she was getting aroused at this so I began to feel encouraged to share.
'The pink ones with Princess on the front. She said I looked like a Princess and said I clearly had a vagina.' I lied a bit to excite her more. I was hoping if she got excited enough she might take her panties off. A few times in the last month she had done just that. She pulled my panties down to my ankles, laid me down in missionary posistion (the girls part) and simulated ******* me. While I never slipped in her warmth excited me greatly.
I could see from her face that she was very excited at what had happened. As we reached my front door, I leaned to her ear and whispered, 'my pussy is sopping wet.' At this she grabbed my ass and pushed me inside.
We went to my room and she tossed her bag on the bed. 'Lay down and take off your pants.' I did so, and she quickly reached over and removed my panties. I laid there hard (as much as I could) eargly awaiting what would come next.
She reached in her bag and said, ' I got something to tell you but I want it to be perfect so close your eyes.' I did so, my heart racing with anticapation. But to my surprise I felt something strange brush against my privates. 'You can open your eyes,' she said. i did, and the smile quickly faded from my face. In her hand she held one of her sister's Pampers.
'A diaper!?!' I exclaimed. 'What is that for?' I asked this but already knew the answer. My protest was feeble and she did not answer me. She grabbed my legs and lifted them in the air. She then slid the Pamper underneath my bottom. She looked at me and with a voice that was filled with sexual pleasure she said, 'suck your thumb.'
I did so. I was becoming accustomed to taking her commands by now. She folded the Pamper between my legs and pressed it against my lower stomach. She took the tapes and fastened each side. She had to streach the diaper, but it fit and held without a single rip or tear.
She smiled and said, 'there, now I can tell you.' She stood up on my bed above me and began to unbutton her jeans. From this vantage point I noticed for the first time a slight wet spot on the crotch of her jeans. She pulled them off and tossed them to the floor. Her panties were soaked in blood and cum.
Still sucking my thumb I felt my penis deflate. She laid on the bed and told me she had ****** my friend Jerimiah that morning. She said she rode him, screaming the entire time. She described how she had begged him to **** her, to not use a condom and fill her with cum. As she described ever moment to me. I began to feel like a little girl and tugged on her shirt. She slipped her nipple in my mouth and finished her story, describing how she had moaned and cried out his name.
I never got to sleep with Jennifer that day. After a few hours I walked her to the bus stop, still wearing my diaper under my jeans. She had brought two more diapers with her along with a half used box of Pampers baby wipes, a bottle, half a can of formula and a pacifer and left them in my panty drawer, which was now the top drawer in my dresser. As we waited for the bus Jennifer whispered in my ear, 'Wet yourself.'
I was still feeling like a baby so I tried. I did not really have to use the bathroom so I strained to push my bladder. I finally did, but to my dismay I messed myself too. 'Good girl,' she whispered, not knowing I had messed myself too. She sat on the bus stop bench and pulled me beside her. 'I love you so much' she said, laying her head on my shoulder.
It did not take but a moment for her to detect to smell, the sitting was causing the smell to fill the air. She lifted her head and looked at me. 'You messed your diaper didn't you.' I nodded, embrassed at this point. She kissed me deeply then told me to go home and change. 'I love you," she called as I began to walk away.
I hurried home, the feeling in my diaper becoming almost unbearable. When I turned onto my street I was horrified to see my mom's car in the driveway. She was home early, and I did not want her to see my condition.
I quickly opend the door and made a beeline for my room. My mom's voice from the kitchen halted my escape. 'Honey,' she said as she walked out into the living room and looked down the hall at me. 'I bought you some things. Come take a look.'
I began to slowly make my way into the kitchen, dreading what was to come, hoping beyond hope I could grab whatever she bought and escape to my room. When I walked into the kitchen I stopped dead in my tracks. On the kitchen table was 3 packs of assorted panties, several dresses, a few skirts, a few tops, pink socks, girl's snickers and dress shoes and even a couple of little girl styled sleeping outfits.
'I know that I can't take you to the store and let you try them on because that kind of humilation could destroy your life. It's your choice how you go in public, but I wanted to get you some things you could wear around the house whenever you wanted. Here, stripe out of those clothes and try them on to see if they...' She stopped mid sentence and the foul odor from my diaper struck her like a brick wall.
'Did you mess yourself?' she asked. I paniced and blurted out the first thing that came to mind. 'I need a diaper change mommy.'
She was shocked at this. She walked over to me and unbuttoned my jeans, and in a single motion pulled them down. I stepped out of them and stood there. My T-Shirt hung down just far enough to cover half of my diaper. She lifted the back of my shirt and placed her hand on my bottom. She then touched the crouch of my diaper and said, 'your wet and messy. But we don't have any diapers sweetie.'
I looked up at her, 'Jennifer brought over three. They are in my panty drawer.' She took me by the hand and walked me into the living room. She pulled off my shirt and laid me on the floor. 'I will be right back sweetie.'
She disappeared and I could hear her enter my room. A few minutes later she returned with the wipes, pacifier, bottle, formula and a spare diaper. She laid the items next to me and slipped the pacifer in my mouth. 'There baby,now lets get you into a clean diaper.' She removed my dirty diaper and with the wipes cleaned my bottom and privates. She took the fresh diaper and slid in under my bottom, quickly fasten the tapes to secure it on me. She disappeared into the kitchen and I heard her begin to prepare a bottom. The microwave turned on for a few moments then my mom returned with a bottle of formula and one of the pink jammies.
'Here you go sweet girl,' she said as she slipped the jammies over my head. Again she took my hand and lead me into my room. After tucking me in she put the bottle in my mouth. The formula tasted strange and I had to force myself to drink. 'Now you take a nap and I will be in here in a bit to check on you.'
Comfy in my diaper I fell asleep, drinking formula and wearing pink jammies.
