A boy loses his virginity to his big-titted babysitter
When I was a young teenager, I was living with my parents in a huge mansion on the outskirts of a major city. My dad George, in his late fifties, was a corporate big shot and he looked the part. He was tall, wiry and muscular and still had all of his hairs, even when they had turned grey by now. Because of his age, people sometimes mistook him for my grandfather. Spending most of his life building his impressive career, he had married late. My mother Nastya was Russian and some twenty years younger than my father. I was old enough to be aware of the fact that people thought my mom was my dad’s ‘trophy wife’ and that she had only married him for his money, but, as far as I could tell, I always had the idea that there was genuine affection between them. Not that I could blame people for thinking of my mom as a ‘trophy wife’. She was a ‘trophy’ that no doubt any man would like to have. She was gorgeous with a tall, lean body that nevertheless sported huge natural F-size breasts and an amazing ass. Her long, raven black hairs surrounded a beautiful face with mesmerizing dark eyes, wonderfully chiselled cheekbones and luscious, full red lips.
When I was a little boy, mom had just been mom, but recently I had begun to notice that she was also a gorgeous female and I checked out her amazing body whenever I figured I could do so unnoticed. Since my parents really weren’t really very prude, I had even managed to get a couple of glimpses of my mom in partial or full state of undress, in the bathroom for instance. Being a horny young teenage boy, I of course jacked off all the time and the images that were burned in my mind of my nude mom had become a major masturbation inspiration for me. Not that I specifically fantasized about fucking my own mother: I just fantasized about fucking. Being a young teenager full of raging hormones, almost any woman would do if I would ever get the chance. Sometimes I even had lustful thoughts about our maid Simone, who was fifty or so and not very pretty.
One Saturday night, my parents were getting ready to go to some important dinner party. My dad was looking sharp as always in one of his hand-tailored business suits and my mom simply looked stunning. She wore a tight black dress that highlighted her huge bosom. The dress was also short enough to leave her beautiful long legs almost completely bare. In addition, she wore a silver necklace and several silver bracelets around her arms. I wondered if the people my dad associated with wouldn’t consider her to be a bit trashy looking, but on the other hand every male at the dinner party would most certainly be jealous of my dad. He certainly didn’t seem to mind my mom’s outfit, judging from the look that appeared on his face when she came down the stairs.
“We have a bit of a problem,” my mom told my dad, “Mrs. Newton just called. She’s go the flu and she can’t come.”
Mrs. Newton was my regular babysitter. I obviously felt I was way too old to have a babysitter, but my parents were adamant I was too young to be left home alone at night. Mrs. Newton was an ugly, old, unpleasant woman so I certainly didn’t mind she wouldn’t be able to make it tonight.
“Guess you’ll have to call Debby,” my dad said, with a weird smile on his face.
“Yeah, I figured,” mom said, “already called her. She can come, but since I called her at the last minute, she won’t be here until in about half an hour.”
“But we should leave now.”
“Then we’ll just have to fashionably late, darling,” my mother replied in her slightly lilting accent she still hadn’t gotten rid off completely.
My father sighed and called me. “Joey, get down here!”
I was in the next room, playing games on the computer, so it didn’t take long for me to do as my dad told. “Yeah, dad?” I said as I walked into the hall.
“Mrs. Newton has fallen ill, so she won’t be here tonight. Instead, another babysitter named Debby will come. She’s a lot younger than Mrs. Newton, so I want you to promise me you’ll behave and not give her a hard time.”
“I promise, dad,” said.
“All right then,” my dad said, looking at his expensive watch, “now we’ll just have to wait for Debby.”
My mother sat down and lighted a cigarette, but my dad kept pacing up and down the large hall. He hated waiting. I just went back to playing computer games until, twenty minutes later, the doorbell rang.
“Joey, get over here,” I heard my mom.
I walked back into the hall to see that Debby had arrived. She was indeed a lot younger than Mrs. Newton. I guessed she was twenty or so. She looked a bit plump and she wore a large pink dress that even I could see wasn’t very fashionable. The dress fell to her knees and under it she wore high black leather boots that really didn’t match the dress. What stood out most about her – literally – were her massive breasts. They were huge, about size H, much larger even than my mom’s. I couldn’t help noticing this at first glance, even when her dress wasn’t really tight or anything. She wore her shoulder length, reddish brown hairs tied back and even though she wore quite a lot of make-up, her face was still rather plain. About as plump and sturdy as her body, but in a cute way. She looked really nice and friendly as well.
“Joey, this is Debby,” my mom said while she gave me a kiss on the cheek, “be nice.”
I shook Debby’s hand while my dad said, “see you tomorrow.”
My parents, already being late of course, hurried off and Debby closed the door behind them. She turned to me and said, “so, what do you want to do?”
The question took me by surprise. Mrs. Newton never cared about what I wanted to do, she just required me to be quiet, not bother her and go to bed on time. “I don’t know,” I said, “I didn’t make any plans.”
“I see,” Debby smiled, “well, now that we’re here together, wanna watch some TV?”
“Fine,” I said and we walked into the large living room, where the huge flat screen television was already on. It was almost never turned off, even when none of us were actually watching it.
Debby told me to sit down and asked me if I wanted something to drink or eat. I replied that I didn’t really need anything but a coke would be fine. She disappeared into the kitchen – leaving me wondering how she knew her way around the house, since I had never seen her before – before returning with a can of coke for me and a bottle of wine for herself. She poured herself a glass and dropped down on the couch next to me. “Is there anything good on?” she asked, nodding in the direction of the TV.
“Well, there’s this action flick coming on,” I said, “that I’d like to see, but it’s probably not really something for girls so if you wanna see something else . . .”
“That’s sweet of you,” Debby smiled, “but I can handle an action movie. If you want to see it, let’s watch it.”
The movie began and we watched in silence for a while, Debby sipping her wine and me drinking my coke. It was a cool movie, full of gun fights and car chases and explosions, but I didn’t really pay as much attention to it as I normally would have. The reason for this was that I couldn’t keep my eyes off Debby’s breasts. They were so big! They presented a sight that fascinated me like nothing ever had before, even when they were still modestly covered in clothing. Whenever I thought she wasn’t looking, I glued my eyes to these wonderful mounds of cloth-covered flesh.
When the movie was interrupted by a commercial break, Debby drained her glass and turned to me. “You’re looking at my boobs, aren’t you, Joey?”
I felt caught. So much for my trying to be discreet while staring at her breasts. “Yeah, er, well,” I stammered.
“I don’t mind,” she smiled, with a mischievous twinkle in her dark eyes, “all men look at them. I’m used to it. So I guess you like them?”
“Yes,” I said, “they’re very beautiful.”
“Thank you,” she smiled again, “would you like to get a better look at them?”
I nearly choked on my coke. What was she saying?
“Do you want to really see them?” she laughed, “without the clothes covering them?”
“Yeah!” I exclaimed, in spite of myself.
“All right then,” she said. She slowly pulled her dress down to her waist, exposing a massive white bra that barely contained her breasts and sported a cleavage that instantly gave me raging hard-on. Debby pulled her dress further down, revealing white panties and black stockings. She pulled the dress down over her boots, threw it aside and said, “you like what you see?”
I just nodded.
She smiled a naughty smile. “Now before I really let you see my boobs, you have to let me see your dick.” While speaking, she was cupping her mammoth breasts, pushing them together and occasionally sliding a hand in between her cleavage.
Mesmerized by the sight of this voluptuous young woman sitting next to me in nothing but her underwear and boots, touching herself, I really wasn’t able to respond to her question.
“Well,” she smiled, “are you going to show me your dick or not?”
Desperately trying to think clearly, I wondered what to do. I could scarcely believe this was actually happening, but nevertheless I did feel some inhibitions about exposing myself to this girl. Even when I hadn’t been raised a prude, showing your dick to your babysitter seemed somehow wrong. On the other hand, she was exposing herself to me so it wouldn’t be fair for me to keep my clothes on. In the end, the argument in my head was simply settled by my overwhelming desire to see her naked tits. Without speaking, I unbuttoned my pants and pulled them down. Then I pulled down my underwear and my dick, as hard as it had ever been by now, eagerly popped out and stood up straight. At five inches it wasn’t that big, but since I was rather small for my age it did appear large in relation to the rest of my body. The fact that there wasn’t that much hair on it yet helped too in that respect.
Debby looked at my dick and nodded approvingly, but didn’t say anything either. She just slowly slipped the bands of her bra down her shoulders before putting her hands behind her back and unfastening the device. Then she simply let the bra fall from her breasts, thus showing me her tits in all their glory. And glorious they were. In spite of the fact that Debby was still young, they sagged a little simply because of their sheer size. It was clear that they were completely natural though and they were beautifully shaped. The mere sight of her large areolae and huge nipples drove me mad with lust. She put her hands on her tits, pushed them together and offered them to me. “You can touch them,” she smiled.
Eagerly I put my hands on her breasts. The sensation of feeling the soft flesh of her giant tits against my own skin was incredible. I began squeezing them enthusiastically with my hands while licking and sucking her nipples, that were soon really hard. While fanatically playing with Debby’s huge rack, I felt like the happiest boy in the world.
After I had been slobbering over her huge chest for a while Debby pushed me away. “Now let me play with you,” she smiled and bent over my crotch. Without hesitation she engulfed my rock-hard cock with her mouth.
I couldn’t believe what was happening to me! The sensation of her hot mouth around my swollen dick, while her huge tits were resting on my legs, was better than anything I had ever experienced before! She apparently very well knew what she was doing as she easily sucked my entire cock into her mouth. She flicked her tongue over the head and scraped the length of my dick with her teeth. The sensations this gave me were so amazing, that I started to come before I realized it. Debby kept forcefully sucking my dick though, not showing any intention of letting go. I came and unloaded an excessive amount of semen in my babysitter’s mouth. She tried to swallow it all. The utter quantity of sperm that was gushing from my balls was so large, though, that she couldn’t gulp it all down and excess semen began dripping from her mouth, something that made for a really horny sight.
When I was done ejaculating Debby let my recoiling prick slide out of her mouth and gave me a broad smile, while my sperm was still dripping from her lips and chin. She sank down on the couch again, licking my semen from her lips. “So that was your first blow job, I assume?” she asked.
“Yeah,” I said, still panting, “it was amazing.”
“I enjoyed it too,” she replied, “I love the feeling of a throbbing cock in my mouth, not to mention the taste of sperm. That was just the beginning, tough” she grinned, “I have much more in store for you.”
She got up and pulled down her panties. After stepping out of them, she sat down on the couch again and spread her legs. “I guess you want to explore my pussy too,” she invited me.
I crouched down between her legs and Debby put her hands on my head, pushing my face against her cunt. I had never seen a pussy up close before, so I found this extremely fascinating. Her cunt was completely shaven and her beautiful pussy lips were glistening with moisture. Carefully I pulled the lips apart with my fingers and I put a finger in her hole. Slowly I moved my finger a little, licking her lips and clit at the same time. Debby began softly sighing and panting, giving me the impression I was doing pretty well. Gaining confidence, I stuck a few additional fingers into her hole and began finger-fucking her, while increasing the speed with which my tongue was caressing her clit. It wasn’t long before her soft moaning turned to loud gasping and when she began to spasm I realized she was having an orgasm.
When her breathing had calmed down again, I sank back on the couch next to her. Debby put an arm around me and kissed me on the mouth. “That was very nice,” she smiled, “now get rid of your clothes. It’s time you learn to fuck.”
I took off my shoes and quickly removed my pants and underwear that had been hanging down on my ankles all the while. Next I rid myself of my shirt and got up, standing in front of Debby fully naked and full of anticipation. My cock was fully erect again by now and sticking out proudly.
Debby lay down on the couch on her back, spread her legs and put them up in the air. “Let’s do it the traditional way the first time,” she laughed, “you do know what to do, right?”
“Yes, of course,” I said, with more confidence than I actually felt. I’d had sex education in school and like any teenage boy I had small, secret collection of porn magazines so I had a fairly good idea of what to do. Still, this was no a masturbatory fantasy, this was real! I still had a hard time realizing that.
Deciding not to think any longer but to simply act, I climbed on Debby and positioned my stiff prick between her legs. She took hold of my cock and swiftly guided it into her wet hole. Having been a virgin, the sensation of my throbbing cock being engulfed by the hot wetness of her hole was beyond words.
My hands resting on Debby’s legs, I cautiously began to thrust. The feeling was great, especially since I was looking at her massaging her enormous tits, her head thrown back, eyes closed, moaning softly. She apparently enjoyed this a great deal too.
In my youthful and inexperienced enthusiasm it was hard for me to control myself and soon I began to thrust faster and faster, causing Debby’s tits to wildly swing back and forth. She began panting louder and louder while I was fucking her like a madman. “Yes,” she groaned, “fuck me! Fuck me harder! Yes! Fuck my cunt!”
The foul language she uttered aroused me even more than I already was – I had never before heard a woman say such words – and soon I felt I wouldn’t be able to hold back my orgasm much longer. Debby felt this too. “Hold on,” she groaned, “don’t come just yet.” I instantly slowed down considerably and felt my imminent orgasm fading away.
”Take it out,” Debby moaned, “and fuck my boobs.”
I was more than happy to comply. I let my prick slide out of Debby’s pussy and climbed on her belly, straddling her. I put my stiff cock between these two awesome mounds of flesh and began to move my cock back and forth at a fast pace. Debby pressed her tits tightly against my rod and soon her massive tits were covered with my pre-cum. The feeling of my rock-hard member sliding to and fro between her moist boobs was wonderful.
“You like that, don’t you?” she smiled up at me.
“Yeah, it’s great!” I replied, continuing my eager tit-fucking.
After I had been going at it for a while Debby grabbed my dick. She sucked on it for a bit, slapped it against her tits, stroked it a few times and then put it back between her giant boobs. I resumed my tit-fucking for a while until she grabbed my stiff cock again, sucking it again and then stroking it once more. She stroke my dick faster and faster, gasping, “give it to me! Give me your sperm!”
I didn’t really need any encouragement at this point, already being on the verge of orgasm again. Grunting I came, while Debby aimed my prick at her face and boobs. I erupted and discharged thick blobs of my young semen on her tits, neck and face. Debby never let go of my dick and when I was done ejaculating, she brought it to her mouth again and completely licked it clean.
I sank back on the couch, completely fulfilled, while Debby was rubbing my semen all over her breasts. “That was fun, wasn’t it?” she smiled at me. “Amazing,” was all I could say.
Debby sat next to me and put an arm around me. She pulled me against her and I rested my face on her massive boobs. I felt my own semen on her tits against my cheek, but that didn’t bother me. I actually found the feeling arousing.
“Tired?” she asked. I nodded. “Don’t worry,” she smiled, “a young boy like you will be ready to go again in no time.”
Since Debby mentioned time, I glanced at the clock on the wall. It was past eleven by now. Mrs. Newton always made sure I was in bed by ten. “Shouldn’t I be going to bed?” I asked. “What if my parents come home now?”
Debby laughed. “Don’t be silly,” she said, “your parents are at a dinner party, they won’t be home until two or three. Besides, there’s still a lot more to explore. You haven’t fucked my ass yet, for example.”
That last sentence almost gave me an instant erection again and it did make my dick twitch. Debby couldn’t help laughing. “What did I say?” She gave my cock a little squeeze. “You’ll be ready again before you know it. However, going to bed may not be a bad idea. A bed is more comfortable than this couch. Let’s go up to your room.”
I got up, but Debby told me to wait a moment. She took off her boots and stockings and when she was fully nude like I was, she got up too. I took her up the stairs to my room. Though larger than an average teenage boy’s room, it looked very much like that nevertheless, with a lot of junk lying around and posters of racing cars and assorted babes on the walls. I put on the lights and sat down on my single bed, eagerly awaiting what Debby had in store for me.
She looked around my room and then joined me on my bed. She put her arms around me and kissed me on the mouth. While our tongues were playing with each other and we were exchanging saliva, she put a hand on my stiffening cock and started stroking it. I put my hands on her breasts again, feeling and kneading those delightful orbs of flesh.
Obviously, it didn’t take long for my cock to become really hard again. However, we just kept on kissing and fondling each other for what seemed like really long time. Between stroking my prick, Debby caressed my balls and I divided my attention between her tits and her pussy, sliding one or two fingers in every now and then and rubbing her clit.
When our mouths had finally let go of each other, Debby said, “now I want you to fuck my ass.”
She sat down on my bed on her hands and knees. I sat down on my knees behind her and glanced at her butt hole. It seemed really tight to me. “Are you sure this is all right?” I asked naively. “Of course,” she smiled at me, “just spit on my ass a few times and it will go just fine. Your dick is surely lubricated enough already.”
She sure was right about that, my prick was dripping with pre-cum. I simply did as she told me. I spit on her ass a couple of times and rubbed my saliva in her butt hole with my fingers until it felt as wet as her cunt.
I put my hands on her buttocks, pushed my stiff prick against her sphincter and carefully tried to push it in. To my surprise, my cock slid in with ease, even though her ass did feel wonderfully tight. I began fucking Debby’s butt hole with long, slow thrusts. After every push I let my stiff rod slide almost completely out of her ass, only to push it back in all the way to my balls with the next. I assumed Debby enjoyed this because she started to sigh and moan rather loudly, screaming obscenities in between. “Yeah, fuck my ass! Fuck it harder!”
I started to thrust faster and faster, increasing my pace until Debby let out a few loud shrieks and I felt her muscles contort, leading me to conclude she was climaxing. At the same time, I was approaching a wonderful orgasm myself. I couldn’t hold back anymore and grunting loudly I shot the last sperm from my balls deep into Debby’s bowels.
When I was done ejaculating, I fell down on my bed. Debby lay down next to me and embraced me. We lay together like that for a while, our sweaty bodies against each other, savouring the moment, until suddenly I heard sounds downstairs. I looked at my alarm clock and saw that it was almost two in the morning. My parents had come home!