Confessions From a Boarding School Pupil
Copyright© 2022 by Drax
Episode 44: The MILF Encounter: Back To Hospital
Pedo Sex Story: Episode 44: The MILF Encounter: Back To Hospital - Welcome to the “Confessions From Boarding School” series. The stories contained here-in will be detailing the sexual adventures and shenanigans I got up to and involved with while I was at and after I left boarding school.
Caution: This Pedo Sex Story contains strong sexual content, including Ma/ft mt/Fa Teenagers Blackmail Coercion Consensual Drunk/Drugged NonConsensual Pedophilia Rape Reluctant Romantic Teen Siren TransGender School Cheating Incest Daughter Uncle Niece Nephew Grand Parent Rough Spanking Harem Interracial Black Female White Male White Female Oriental Female Hispanic Female Indian Female Anal Sex Massage Oral Sex Tit-Fucking Voyeurism Babysitter Public Sex Small Breasts Teacher/Student Prostitution
After a few minutes of driving in silence, Maria turned to me and asked “Do you have a girlfriend?”. I smiled and replied “I thought I was dating your daughter, but I suspect I might have an older girlfriend very soon”. Maria smiled and replied “I think that is a distinct possibility”. I was suddenly nervous upon hearing her last words, this would not be the last time that I would be nervous as you will read about later on. As we turned a corner, Maria stole a glance at my crotch and the erection that was bulging in my pants. “I see that you’re all ready to go” Maria says, reaching down and giving my crotch a squeeze “I cant wait to see this and the rest of you in all your naked glory”.
I nodded and replied “And I cant wait to see you in your naked glory as well”. After a further 10 minutes of rather aggressive driving, we arrived at Maria’s house and parked in the garage. “Are you up for me sucking you again?” Maria asked, to which I replied “Where?”. She did not answer me but did smile as she leaned over and down towards my crotch. She got my cock out of my trousers and pants kissed the tip then took it into her mouth once again. “I might not last long” I told Maria “You did such a good fucking job last time”. I sat back and enjoyed the feeling of being blown off by Kristina’s mother. Despite having had a blowjob from her just a short time ago, I was still rock-hard as she sucked me off again.
I looked down at Maria as she worked on my cock and smiled; I was getting a blowjob from the mother of a hot young Ukrainian girl I’d fucked. And soon enough I would be fucking Maria. Kristina had been an absolutely spot-on, top-notch fucking amazing fuck, and so far, her mother’s oral skills were just as good as hers. I kept one hand on Maria’s head which I held gently while I put the other on her bum and squeezed it gently. I then slid my hands into her trousers, into her panties and squeezed her bare bum directly. I smiled down at Maria once more before I sat back closed my eyes and enjoyed the feeling of her sucking my cock. As I sat there being sucked off, I oddly enough found my mind wandering onto Brentford Court.
Specifically, I found myself thinking about the first time that I’d ever had sex. Losing my virginity to virginity Kara in the bathroom was not ideal, nor was it the place where I would’ve picked to have sex for the first time. But it was the place where it had happened and it was indeed a very fond memory of Kars that I had. Now before you all go saying that I’d lost my virginity to Li, let me reassure you that is NOT the case. I’d been blown off and tossed off by Li many times before I’d fucked Kara, but I’d never had sex with Li before I screwed Kara. If I’d had sex with Li before I fucked Kara I would still have fucked Kara. Mainly because Kara was such a great fuck.
And also because Li was stingy when it came to sex and when we finally did get to fuck, she was not very good if I was being honest. I was shaken out of my thoughts of Brentford Court when Maria stopped the blowjob and asked me “Having fun so far?”. I nodded and replied “Indeed I am; you’re so fucking good at this”. She sits up, kisses me passionately for a few seconds before breaking the kiss and returning to the blowjob. I slid my hand back down her trousers, back onto her bum and resumed squeezing and rubbing it gently. I closed my eyes as she worked on my cock, the feeling was so relaxing I could have fallen asleep. Plus rubbing and squeezing her bum also helped me feel relaxed.
Being sucked off in a car was something I enjoyed as there was something kinky and being blown off by a middle-aged woman in the front passenger seat of her car; even if the car was parked in the garage. For the next few minutes, I just sat back and enjoyed the feeling of Maria sucking on my 14 year old cock. “I’m almost there” I tell Maria, not wanting the blowjob to end “Oh god I’m almost there”. I grit my teeth as I try to hold off on cumming for as long as I can, but it is no good. “I’M CUMMING” I cry out, and a second later that is exactly what I did. “AHHH” I cried out in pleasure as my cock shot its load into Maria’s mouth. I sighed in pleasure as Maria clamped her mouth around the base of my cock.
“Wow” I say with a pleasured sigh as Maria sits up “That was fantastic”. She smiles and replies “Indeed it was; I could do that to you all day”. She gets a bottle of water from the glovebox and uses it to wash her mouth out, thereby getting rids of the cum I just put in it. “So, would you like a drink before we retire to bed?” Maria asked with a smile as we head from the garage and into the kitchen. “I’d love a coke” I reply. Maria goes to the fridge and gets two cans of “Jack & Coke” and hands one to me. “So, shall we retire to bed now?” Maria asks as we open our sodas and take a sip. “We can take the drinks to bed with us” I reply. “Now that is a good idea” Maria says “Let’s go”.
Maria takes me by the hand and leads me upstairs. And as we go, I steal a few glances at Maria’s ass. “Enjoying the view?” Maria asked, to which I replied “It is a fine view, so yes I am”. We got to her bedroom and as I downed the last of my Jack & Coke, she pushed me up against the door and kissed me passionately. I was caught off guard for a moment but soon got into the kiss. I placed my hands on her slim waist and held her gently as we kissed. We kissed like that for a few moments before Maria broke the kiss and downed the last of her Jack & Coke. “That was good” She said, tossing the can into the waste basket “Now we can go to bed”. I nodded and replied “Never argue with a lady”.
We both got undressed, and I was in my pajamas, I was naked before Maria was. “Now that is a sight to behold” Maria was, admiring my naked form. “You like?” I asked, to which Maria replied “Hell yes I do”. She stared at my cock for a few moments then resumed getting undressed. She was soon also naked and put her hands on her hips and asked “And I take it you like what you see?”. I nodded and replied “I thought your daughter was hot, but you are total perfection”. She stepped up to me, placed my hands on her hips and wrapped her arms around me and just hugged me gently. I actually liked naked hugging and held Maria gently. We just stood like that for a few minutes, naked and hugging.
I slid my hands off her hips and slid them onto her bum, which I squeezed gently. “That’s nice” Maria sighed “This is just what I need”. I smile and reply “I’m glad you like it”. I was glad that Maria enjoyed naked cuddling as much as I did. We stayed like this for a further few minutes before Maria broke the hug and said “Let’s get in bed”. We moved over to the bed and got under the covers, Maria cuddled up next to me and draped her right leg over mine as she gently stroked my dick. “So, what do you want to do now?” I asked. “Can we just cuddle?” Maria asked, to which I replied “Whatever you want to do is just fine with me”. And so for the next few minutes, we just lay there in total silence, wrapped in each others arms.
I enjoyed naked cuddling, and if this is what Maria wanted to do then that is what we would do. As we lay there naked and in total silence, it occurred to me that this was my first appointment outside of the hospital and that it was going better than I thought it would. If all my appointments outside the hospital went this well then I could foresee a great many more in my future. Laying there naked just cuddling a woman was something that I didn’t do often enough and that I would have to see if I could do it more often. Maria stopped stroking my cock and kissed my cheek and asked me “You do not mind being with a woman my age?”. I shook my head and replied, “Beauty does not know age limits”.
I know what I had just said sounded incredibly fucking corny, but it was the truth. “I can see why Kristina likes you so much” She says “You always know just what to say”. I had gotten used to women of a certain age that I saw asking me if I was OK being with them. “Let’s forget about Kristina” I tell her “This is supposed to be about you and me, not her”. While I enjoyed sleeping with Christina and thought she was genuinely very fucking hot, this time was supposed to be about me and Maria. And I know telling Maria that also sounded corny, as well as it being the truth it was also the right thing to say to keep her happy. “There you go again, saying just the right thing” Maria says, kissing me gently.
She kisses me after she says to me “How you don’t have a girlfriend yet is beyond me”. The reason I did not have a girlfriend yet was very simple and that was my job at the hospital; that and I’d not yet met anyone that was worth giving up my job for. “If I had a girlfriend, then I could not do my job at the hospital” I told Maria “No woman wants a guy whose job it is to sleep with other women”. This was similar to what I’d told that fitness-obsessed paramedic Christi when I’d been with her. In truth, I honestly did not want a girlfriend yet as I was enjoying my job to much, but that did not mean I was opposed to finding a girlfriend. After loosing Ariadne, I’d sworn off a girlfriend as I was now enjoying my job to much to find one.
“Your job helps women who want sex but don’t have the time to find a partner” Maria tells me “I think that is so good of you”. I had not thought of it like that; I was simply doing it because I liked sex and the women that I porked tended to be good looking. “Helping the women is easy when you are so hot” I reply. “There you go again, saying the right thing” Maria says with a smile. “It’s the truth as well as the right thing to say” I tell her. She smiles lovingly at me then leans in and kisses me passionately as I gently rub her bum. “Would you like me to rub your back?” Maria asked, breaking the kiss. Now I have to admit that this was the first time I’d been asked this by anyone.
“Are you sure you don’t mean you want ME to rub YOUR back?” I asked. “No, I meant what I said” Maria said with a smile “Now, turn over”. I did as I was told and rolled over onto my front. Maria reached over and got some body lotion from the drawer. She knelt just below my back and put some of the lotion on me. “That’s cold” I said, to which she replied with “You’ll soon not notice it”. She tossed the lotion aside then began to rub my back, and it felt so good. “You just lay there and let me rub you” Maria says “It’s nice to be able to do this to someone”. I smiled and reply “It feels good...”. What I had just said was indeed the truth as it felt fantastic having a massage, even better that it was a naked massage.
As I lay there with Maria massaging my back and shoulders, I could not stop my mind as it began to drift. Even though it had been explained to me by Angeli and Christi, I could not help but think about why women liked me so much. Girls my own age I could understand, but older women was a different thing. If they found me attractive enough to want to take me to bed would that note make them pedophiles and me a victim of abuse? The legal answer is “yes” but the real and proper answer is “HELL NO”. I am a willing and enthusiastic participant in this and anyone who says that I am a “Victim of abuse” is talking out of their fucking asses. I am shaken out of my thoughts by Maria.
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