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The Weekend Changed Everything
By: baby jerbear
On my twenty fifth birthday, my friends took me out for a night on the town. After about the third bar, I was pretty much snookered; that's where I met her. She stood 5'10", a full 3 inches taller than I was, she had the most beautiful face I'd ever seen before that day and since. She had 36 C breasts, which are great for me, I don't like it when breast are too big and fall out of my hand, and the most fantastic legs I'd seen on this side of heaven. My friends and I had walked up to her and started talking. The next thing I know, it was 2 hours later, my friends had all gone (they were my ride), and the bar was about to close. I was obviously in no position to drive, and since we had gotten along so nicely, she had offered to let me crash at her place for the night. By that time, I had had way too much to drink and was not too coherent when she offered so I accepted.
The next morning I woke up in her guest bed. By the time I wiped the groggy out of my eyes and crawled out of bed, I realized that I was in nothing but my white undershirt, and a big, thick, noisy diaper.
As I came out of her guest room, I noticed that the diaper I was wearing was a little bit saggy. I had it in my mind that I was going to tell this woman off, "how dare she put me, a grown man in diapers," I thought to myself as I pulled my obviously wet and sagging diaper up. As I approached her kitchen table, I saw the sexiest woman I had ever laid my eyes on.
"How do you feel about having a bit of breakfast with me this morning," she asked in the sweetest voice that I had ever heard. As she asked me that question, I completely forgot about telling her off, and even forgot that I was wearing a big, thick, wet, soggy and noisy diaper. We had a pretty good conversation over oatmeal and cantaloupe, and got to know and learn about each other a little bit better. Had she not commented, "I am glad I put that diaper on you last night," I would not have even remembered that wearing one wasn't anything out of normal.
"Oh yeah," I continued calmly, "I wanted to ask you about that. How in the world did I get into this diaper? I mean come on, the last time I needed diapers at night I was five years old. Don't you think it's a bit much?"
"You mean you don't remember?"
"Remember what?" I replied.
"You came into my room in the middle of the night and told me you had to pee and that you didn't make it to the toilet exactly. I got up to see what you did, and sweetie, you peed all over my bathroom; everywhere except the toilet. I didn't want to take any chances. I have a pantry full of thick, adult size disposable baby diapers because my last boyfriend was actually a bed wetter and those are the only ones that never leaked." I was silent as she continued, "so since I have a bunch of them left over, I thought this situation required one. Look honey, I really like you. You have this innocent quality about you and I didn't want a problem like this to come between us in the future."
"Future? You really think we have a future together?" I replied eagerly. How could a woman this beautiful, and with such a sweet personality want to be with me? I thought to myself.
"Look," she said, "I'll tell you what, let me get that diaper off of you. If its completely dry, I'll apologize and under no circumstance will I put you in one ever again. BUT, if its wet or messy, or both, I'll clean you up, and anytime in the future we sleep in the same bed, or even the same house or apartment, you must let me diaper you in the evening before bed time regardless of whether you are sober or not." I was still stuck on when she said that we would be sleeping together in the future that I forgot I was in that wet and soggy diaper yet again and agreed.
"Okay," I said. She replied, "I want to hear you promise me, a man is only as goods his word."
"I promise," I replied snapping out of my haze. She took me by the hand and led me to get living room where she then sat me on the floor. I felt my diaper squish with the amount of liquid that was in it when she said, "now you just wait right here. I'm going to go get the wipes and changing mat." She came back to me with a bag and a mat, set it all up on the floor, laid me down on it and undid the fasteners on my diaper.
"Now here's the moment of truth," she said seductively as she lifted the front of the diaper from my crotch and laid it down.
"My my, look how wet you are," she said touching my nose with her index finger as if she was really talking to a baby getting a diaper change. I got all defensive and replied, "Come on, you don't have to talk to me like I'm a diaper dependent toddler. I'm a grown man you know." She replied as sweetly as she could placing her fingers on my mouth, "Shhhh sweetie. You don't have to get like that with me, I know your not a real baby. You just have to let me diaper you before we go to sleep together from now on."
"I know," I replied, "I remember." As she wiped my penis with with baby wipes, it started to grow. Now on a side note, I've never been a huge man down there. Average I'd say. At my maximum hard on, I get about 5 1/4 inches. I know this because I've measured. Back to the story now. My hard on was growing as she softly wiped and stroked my dick with the baby wipe in her hand.
"What a cute wee wee you have there. It's not that big, but it's not terribly small either." By this time my five inches were raging as hard as it could when I said, "I know I'm not the biggest man down stairs, but trust me I'm not the smallest. You don't have to make fun of me."
"Oh I'm not making fun," she continued seductively, "I just think it looks really cute, that's all. I'll tell you what, if I continue stroking you off until you cum, will you promise to let me get off and cum?" She asked.
"I was feeling so much pleasure I said, "Oh yeah I promise!"
"Remember a man is only as good as his word." I thought this was a weird thing to say, but since I was happy I didn't think too much into it and replied, "I know girly, I promise you'll get off." In the back of my mind I was scared seeing as how it had been about 5 years since I had had sex with a something other than my thoughts and my hand. Five years since I had sex with a woman, how can I deliver on my promise in she thinks my dick is cute? Will I find the clittoris? I quickly suppressed these fears as all my cum spewed into the baby wipe in her hand. It only took her about 3 minutes to get my cum out. At that moment she asked me if I was ready to live up to my promise. I said, "Of course I am, I just need to get hard again." I didn't think too much of it when she replied devilishly sounding, "oh you just let me worry about that sweetie." She then directed me to my knees and said, "Now open your mouth and close your eyes and you will get a BIG surprise!" I quickly obeyed. The next thing I knew she had her hands on the back of my head and I felt something big glide into my mouth. I opened my eyes to find a huge dick, almost double the size of mine, going in and out of my mouth. I knew then and there what the undertones in her voice earlier meant. She was an extremely passable tranny with a REAL monster cock attached to her. Five minutes later she still hadn't cum, but she did take her cock out of my mouth and ordered me to go into her room, to her nightstand and grab her a condom. I said, "one, I had no idea you had a cock. Two, that thing is HUGE, twice the size of mine I think."
"I know," she replied, "9 1/2 inched baby." I started to continue, "and three..." but she cut me off "come on baby you promised me! And besides, more cock means it takes me longer to drain all my cum out! Now please, I have a condom in my nightstand next to my bed, please get it. I'll tell you what, if I have more than one condom in there I'll let you retain some of your manhood and fuck me baby." Again getting lost in her beauty, I obeyed and went to the nightstand. As I opened it up my newest fear became a reality, only one condom there.
"Here you go sexy," I said as I handed it to her. She unwrapped it, slid it on, bent me over the arm of her couch, and pounded me so hard for the next 5 to 10 minutes. It was by this time that she then pulled me up from being bent over the couch. We started making out as she took me to her room, laid me on her bed with my legs in the air and preceded to pound my virgin ass for another 5 minutes or so. This whole time I was getting my brains fucked out of me, I had not once touched my own wee wee. It was about this time I saw cum fly out of my penis and onto my stomach. Once this happened, she flipped me over doggy style and fucked me silly for another 5 or ten minutes until she finally blew her load. She had a lot of cum in her, and she blew it all into my now stretched ass, which in turn was starting to run down my leg. I then just collapsed on the bed as she walked off into her bathroom. I heard her start the shower. She then walked out of the bathroom towards me, collapsed on the bed, and said, "come on sweetie, we need to get cleaned up." She then pulled me up and led me to the shower. As we both got in we started making out and rubbing each other all over. I could tell we were both getting hard ons again as she said "turn around for me." the next thing I know, I'm being pushed against the wall and being fucked by her yet again, except this time, bare back. She fucked me good and hard another 15 straight minutes or so when she finally pulled out. By the time she did pull out, my cock had already managed to leak more gewy cum. She then washed her dick off with a little soap, rinsed it and proclaimed, "Please put my dick in you mouth and finish me off!"I sucked her off for another five minutes until she blew more cum right into my mouth. After I had swallowed all of her cum, under her direction, we preceded to clean each other off really good. I wanted to make sure that her boobies got nice and clean so I even starting to suck on them after we rinsed the soap off of us.
"You know sweetie, that's how I know you really are a baby." How's that?" I replied.
"Because your sucking my breasts like one right now." I didn't respond to that one but instead just continued to suck her beautiful boobies. After we dried each other off really well, she led me to the living room to where her diaper bag and changing may still lay on the floor.
"I better get you in a clean, fresh diaper now shouldn't I," she said rather rhetorically. I replied, "it's the middle of the day, I thought you only were going to diaper me at night?"
"Baby after sex like that I know we are both tired and need a bit of a nap. And besides, after the fucking I gave you, your going to need to be in diapers for a few days seeing as how stretched out your asshole is now. Trust me baby, you won't be able to hold anything in when nature calls even of you tried. At least not long enough to make the toilet." I decided to trust her with that, as I didn't want to poop myself in any big boy underwear. So the rest of the weekend I spent at her house in diapers and constantly getting fucked by her big, tasty cock over and over and over. Sunday night had finally come, and with the weekend finally over, she walked me to the door and said, "you, my precious, are a much better cock sucker than anyone that has ever given me head."
"Wow," I replied, "yours is the first one I've ever sucked."
"I find that extremely hard to believe sweetie! You're such a natural. You have no gag reflex for my 9 1/2 inches." I protested, "I promise you, I've never had a cock like yours." She giggled as she said, "and with me you never have to worry about performing with your cock ever again."
"No," I said quickly, realizing how my last statement sounded.
"I meant I've never sucked a cock or been ravaged by one ever before."
"Okay honey. Whatever you say. All I said was that you are such a natural cock sucker."
"Oh ok," i said. Well I had fun even though I was on the receiving end the whole time." I replied as I walked out the door and across the hall of her flat to the elevator.
"I'll call ya lover!" She exclaimed.
"Promise?!" I replied. She smiled and blew me a kiss as the elevator door opened and then closed with me inside. I returned to my flat and asked myself whether or not I wanted to shower that night or wait until the following morning. As I walked into my room and started taking my clothes off, I remembered that she had changed my diaper about half an hour sooner. And since I was still dry, I decided that I was just going to go to sleep and shower in the morning. So I went to bed in just my undershirt and my diaper.
So to update you guys about today, it's now 3 years later, we are married and I couldn't be any happier. For the past 2 years I've been kept in diapers 24/7. Good thing too. Now I really need them. Since she has kept me in diapers so long, and because she can really stretch my ass out, I have totally become diaper dependent. On another note, I haven't put my penis into anything since it had been in a baby wipe in her hand that first fateful fuck that night that changed my life. So as a result it appears to have shrunk a little bit. But it doesn't really bother me any though, since I get the most amazing orgasms when she pounds my tooshie now. Turns out, she is a big executive at an accounting firm and I am now her secretary. I get 3 chances for a diaper change at work usually. Discretely of course on my morning and afternoon break as well as the last 15 or so minutes of my lunch hour. Of course it stinks when she's in all day meetings. I have to suck it up those days. I get in trouble if I change my own diapers. My favorite lunch breaks are the days she likes to feed me her cum for lunch. Once i swallow all her cum, she makes me get her hard again, she pulls my pants down to my ankles, my diapers down to me knees, bends me over her desk and fucks me silly. Once she cums in my ass she pulls my diapers up real quick so none of it drips anywhere and then pulls my pants up. The rest of those days I don't get my diaper changed until we get home, so I have to sit the rest of my day with her wet, sticky cum full in my diaper; and trust me when I tell you she has a lot of cum. I know she loves me so when she then slaps my diapered bottom through my slacks as hard as she can and says, "now get back to work my girly little slut."
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