This is a long final instalment but I hope you enjoy.
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I needed, rather than wanted, to remove Deb’s tonsils from my cock when my legs started to buckle. She was giving me my first deepthroat and face fuck. At that point we were both still wide-eyed and in a state of shock. I remember thinking - WTF do I do now?
I was physically paralysed from being sucked deep down a MILF’s throat, pretty much without warning. Out of necessity, rather than any well-thought out manoeuvre, I told Deb to take me to a bedroom. On her knees, she unlatched herself from me. Looked up at me with a somewhat messy face and paused. That moment maybe felt like 20 seconds - it was probably only two seconds. Deb then said “Are you sure?”.
I remember, for maybe the second time that morning (and perhaps the last time ever with Deb), me having a moment of hesitation. A sort of “Holy shit” and “This is fucking crazy” type hesitation.
It was a defining moments in my life - like the moment when I asked her if she wanted me to be her toy boy, about 5 minutes before. I felt past the point of no return. “Yes” was obviously my response. But as into it as I was, going to her bedroom to have sex honestly felt like a sequence that had to happen rather than a “I MUST fuck you now” type feeling. That developed later, in an extreme way.
Into the bedroom we went, with me taking the lead and us mutually encouraging each other. The pace slowed as we had all the time we wanted. I helped Deb take off her clothes and finally got a feel of her breasts - the same beauties I had noticed the night before. 30DDs and I though surprisingly perky/firm for a 39 year old mom. Responsive nipples for sure.
I teased her with my kisses and recall she seemed nervous, much more than me at this point. A little stiff, like my cock, but her beautiful eyes were wide open like her senses were on hyperdrive. She lay down on her back, with me on top, caressing her (having also removed all my own clothes). I moved from kissing her lips, to her breasts and then her belly button and back again. I remember spreading her legs and finding an unruly bush which I had forgotten to anticipate. Deb’s comments about being overdue a wax on the drive back to hers the night before made sense all of a sudden.
I had found what I was after though and it was very, very wet. I needed to tasting her and so used my tongue on her pussy and clit for several minutes. I was easing myself into things and no longer felt paralysed. If anyone was paralysed now, it was Deb.
I went back up to her tits and stayed there a while, momentarily contemplating my life choices. Contemplation swiftly over, I remembered I had a condom in my wallet and said I should get it. Deb said I didn't need one but I told her it was for the best and got it anyway. I put the dom on whilst we both nervously laughed at what we were doing.
Deb had a fit body - probably better than I expected. Great tits, a reasonably firm tummy and a fantastic pussy. Long toned legs. Physically, her signs of aging were subtle, even though she was pretty much old enough to be my mom.
With Deb reclined on her back, I penetrated her in missionary - again, starting slowly. My god she was wet. But her 39 yr old vagina felt fantastic, despite the condom. She later told me her tightness down there might have had something to do with her requesting the surgeon put an extra stitch in after a tear from childbirth!
As we went through the gears, I felt like Deb was rustier in the sack than I was. I would be lying if I said otherwise. But I was lost in her. I needed to be deep inside her and we seemed to fit like a glove. Her thighs and whole vulva area seemed to envelop me in a way that no other woman’s had.
We soon got into our stride and my own experience and skills were not letting me down. Although I was 18 years her junior, and only 21, I had been fortunate to have had plenty of sex. The benefit of previously having a long term sexual partner (the ex GF) who I had been able to regularly hone my skills with - up until a few months before.
I am a pleaser. One of those guys who gets off from his partner getting off and won’t cum before they do. So I pursued her orgasm with determination and focus. Fortunately my age and fitness meant stamina was on my side but Deb felt so dam good. I don’t recall switching positions but I did mix up the pace a couple of times. I think I might even have withdrawn temporarily to pleasure her clit with my tongue some more and make sure she knew I was going to really satisfy her. Maybe I wanted to prove myself after talking the good talk. Maybe she was taking me for a test-drive.
The scenario was extremely arousing. There I was, switching between being tongue or balls deep in a true MILF who seemed game for my sexual advances. She’d reassured me in the hallway with her mouth, so now it was my turn to pleasure her.
I eventually found the sweet spot and got her close to an orgasm. Her thrusting, moans and facial expressions did their thing for me too. Shortly after she climaxed, I exploded into the dom. It was fantastic. I have no memory of how long it was that we had sex for. It could have been 10 minutes or an hour! I remember feeling exhausted but alert, if that makes sense.
It wasn’t late and no-one was drunk. There was no dark room or reason to close our eyes and not talk to each other. We couldn’t hide, or blame alcohol for what we’d just done. I lay their smiling. Still a little nervous but much less than I had for perhaps the last 12 hours or more. I think we were both processing it all during a few minutes of pillow-talk.
So we eventually got dressed and had a proper chat. We agreed it had been great and we fancied each other. We were single adults who weren't hurting anyone. It left the door open to us becoming lovers just like I hoped. We didn't make any hard or fast promises but we didn’t need to.
Obviously I pointed out that I had a couple more days of work to finish the tiling job in the basement. It was a genuine reason to go back the next day - after-all, I still hadn’t been paid. Deb said she would be free the next day so we should have a good night sleep and chat more then. It think it was implicit that more than chatting and work would be on the cards.
So I went home and had a much needed full night’s sleep. I went back the next day to continue the tiling. I had an erection the whole journey there. When I got there I felt a little unsure how to greet Deb. I went in for a brief embrace and kiss, which to my relief was welcomed by Deb with a sexy smile and squeeze of me ass. Clearly we were both still on the same page.
I did a morning’s work and by lunch Deb had cooked up a plan for me to stay over with her that night. She persuaded me (I didn’t need much persuasion) to call home and tell my parents that I’d been invited out to another party again and would be staying round Deb’s.
It think it was hard to concentrate on my work that afternoon, whilst also thinking about the evening and night with Deb. I’m not sure what time I clocked off, but what I am sure about is how I spent that evening/night. Oral sex and intercourse, and lots of it. I’m not sure how many times we orgasmed but I do remember us exploring each others bodies and minds much more thoroughly (and comfortably) than the day before. It was no holds barred.
We were turning what could have been a one-night stand into a committed MILF/toy boy relationship. At every stage when we highlighted a potential consequence of our actions, we had a reason it should not be an issue. There were no casualties - just upsides. Over the rest of that day and the next, we became more and more comfortable with each other. Mentally and physically - we just clicked. I now wonder if pheromones had something to do with how we felt.
We gradually set expectations for our relationship but only in line with what our sexual desires. We didn’t kid ourselves about it having a long-term future and so that enabled us to live in the moment. It is an understatement to say I was enjoying it.
Deb found more work for me at her/her mom’s place the next week. There were suddenly more parties/social engagements too that I told my parents I was getting invited to. All friends of Deb’s and therefore it made sense for me to stay over at hers. Eventually it would become obvious we were in a relationship of sorts and we would tell everyone but that didn’t happen for a while. When it did, it was fine. Only her mother and one of my older friends openly expressed reservations. Everyone else - my parents, her dad, her friends, my friends etc accepted it.
At some point we spoke about contraception - Deb brought it up. We both agreed a condom took something away from our pleasure and we agreed that we didn’t need one for contraception or STI reasons. She was on the pill. We had both had limited numbers of sexual partners and no record of STIs. I didn’t take much persuading to go bare. Her pussy was just beautiful - inside and out.
Our sexual appetite for each other became insatiable. There was nothing stopping it. Within a few days of first sleeping together, we couldn’t keep our hands to ourselves. My cock was like a magnet to her at all times. She was only too happy to take it at all times. She occasionally fed me and I occasionally did some work.
The rest of the time we just fucked and fucked and fucked, and fucked again. We took it in turns putting in the physical effort (it never felt like effort) but our stamina and fitness kept us going for hours each day. We were fortunate not to have many commitments that summer. Deb’s son was with his father for much of the holiday and I had no significant commitments to take me away from her for any length of time.
It sounds like a fantasy - it basically was. Just a fantasy I could actually live out. I was getting unlimited, guilt free/strings free, sex from a hot MILF who really knew what she was doing in the sack. She was getting satisfied by a hot young male who reminded her she was attractive and more than capable of turning him on. I wouldn’t be being truthful unless I confessed to her teaching me a thing or two - particularly how to make her orgasm repeatedly from intercourse.
I remember us getting a little sore eventually but the natural lubrication and “fit” was fantastic. Any soreness never seemed to be bad enough, or last long enough, for us to stop our trajectory. Whenever Deb tired physically (usually before me, despite being surprisingly fit), she simply let me do the work - usually in missionary, spoons or a variation of those positions. Occasionally doggy/prone with her fingering herself.
Her appetite to have me inside her grew and grew like an addict. I was giving her at least three, but sometimes four, five and maybe even six orgasms when we had sex, before I came once. Sometimes, after my first jizz, I would stay inside her until I got hard again a few minutes later. She would only need to writhe slightly and we would both be at it again, her getting turned on and me giving her another orgasm or three before I came again. I must have averaged 3 or 4 orgasms a day (I was 21!) and her 8+ easily.
A couple of positions seemed to work magic for us both. One was with her lying on her back and me being on top (or standing, if she was on a high enough surface like a table / desk) with her feet over my shoulders. This allowed me to penetrate fully and hit her G spot. I could also grind my pelvis against her clit. Occasionally her legs slipped off my shoulders and I would pin them back and further apart with my arms or hands, spreading her wide. That was great too - she was flexible and I could really control her body and orgasms in that position.
I enjoyed teasing and got turned on edging her (and myself in the process). Sometimes, before I penetrated her properly, I would move my cock around the general area - maybe put the tip in, then pull slowly out. Then slowly back in but going ever so slightly deeper. A few times like that - not even half in, then very slowly all the way out. I’d then sometimes go down on her for a while but wouldn’t let her climax. I would go back to penetrating her a little or use my fingers and I’d have her shaking and thrusting for me. A grown MILF desperate for my cock. It was fucking brilliant.
So this all lasted about a year - after the summer we had to work around her childcare commitments and I also needed to do more work but it only made us want each other more. She moved out of her mum’s place at some point and that was great because her mother wasn’t particularly friendly or accepting (not just about Deb and me). My parents were fine with Deb staying round our house too - even if that was a little strange given that she continued to work part time for my dad.
As the days and weeks went by there were many special moments. Some of these could be separate stories in their own right but I’ll leave you with a sample to think about...
-The time Deb actively encouraged me to pursue girls nearer my own age (like her friend’s daughter) and yet was clear with me that it wouldn’t get in the way of our physical relationship. A complete “Hall Pass”.
-The time we drove somewhere together for the first time in daylight and she insisted on giving me a blow job all the way back to hers whilst I was driving. She told me I could ask her to suck my cock whenever I wanted it and she would oblige. That made driving more interesting from then on.
-The time I told Deb about my shower/wet hair fantasy and the next day she surprised me by joining me in the shower and without saying a word, started to deepthroat me. One of the few times I let myself cum down her throat.
-The time we were driving somewhere again and Deb was wearing a dress. She took her knickers off, put her feet wide apart on the dash (without caring who could see) and encouraged me to finger fuck her until she came. It was a busy highway with lots of oncoming traffic.
-The time she picked me up from my place but couldn’t drive more than 1/2 mile before abruptly pulling off the main road into a small cutting/track. She told me to fuck her on the hood of the car. I did as was told. It was daytime and there was occasional traffic passing by within 10 metres (behind a very thin/weak hedge) of the main road.
-The time I requested Deb try squat riding me and she really went for jt to please me. But in the process she came and squirted (but didn’t realise and we both thought the other had peed on/in each other at first). Neither of us knew what squirting was back then but we sort of figured it out eventually because it seemed to only happen when she rode me in certain positions and it didn't smell/look like piss.
-The time we went away for the weekend and at some point actually fucked ourselves to sleep at the same time somehow.
-The countless times she woke up early in the mornings but couldn’t just let me sleep so would grind her ass against me or wake me with a blow job so that she could get me to fuck her and give her more orgasms.
-The times we went hiking in the mountains and decided we just needed to fuck in the open air on the trail. Nearly got caught a couple of times.
-The time she drove me out to a special place to her in a violent thunderstorm and ordered me to fuck her as hard and fast as I could in the rain.
-The time she got her (also very hot) mom friend round hers at the same time as me and plied us all with alcohol before attempting to initiate a threesome. The other woman was up for it but I didn’t have the memo beforehand and wasn’t mentally prepared, so it didn’t happen. But I really enjoy knowing it was mine for the taking.
-The time she wanted to make me cum just one more time than I actually seemed physically able to (having orgasmed two or three times already that session). She demanded I hold her hair/head with one hand and masturbate into her wide open mouth with the other hand. She wanted it so bad and would always swallow, so it was rude not to.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/lslwcv/i_m_was_the_21_year_old_toy_boy_she_f_was_the_39/
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