I [M] was the 21 year old help, she [F] was the 39 year old customer who ORDERED me into bed. I became her toy boy. Part 3 [MF]

In case you missed it –
Part 1 is [Here](https://www.reddit.com/r/gonewildstories/comments/leb06u/i_m_was_the_21_year_old_help_she_f_was_the_39/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)
Part 2 is [Here](https://www.reddit.com/r/gonewildstories/comments/lf2367/i_m_was_the_21_year_old_help_she_f_was_the_39/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

In this part (part 3), my time with Deb gets very uncomfortable. Then it gets better. Part 4 will round off the series.

I’ve never written about this experience before and it’s my first try writing anything sexual. Hope you like.

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I parked up and gave Deb’s arm a gentle rub to wake her. She opened her eyes slowly and turned to me with a sleepy but sexy smile. “Let’s go to bed” she said with a grin.

She was looking attractive despite/because of her drunken flirty state. The long curly blonde hair was now down around her shoulders (no longer in a scrunch) and she looked sexy in an untamed way.

When we got inside the house she threw her bag on the floor, kicked her shoes off and said she’d be back in a minute. I stood there, feeling like a stranger in someone else’s house, which I was. The front door opened into a hallway which led to an open plan living/kitchen area. That’s where she left me so I decided to pour us a couple of glasses of water.

I’d drunk mine before Deb strolled back in a few minutes later. She’d changed into her cute pyjamas that I’d seen earlier. There was no dressing gown now though. That meant her figure was more visible. She had quite a tight tank-top on which, without the dressing gown, revealed to me surprisingly large natural breasts, and nipples. They were a 32DD I later established.

I tried to give her the water I’d poured but after just one sip she shouted “Bed time!”. She smiled at me over her shoulder as she turned around and playfully said “Come on then, don’t just stand there!”.

I said sorry and started to walk over to the sofa which we’d agreed I could sleep on earlier. But before I had taken a couple of steps, she’d skipped across the room and grabbed my hand. My heart skipped a beat. “Not yet – come and lie down with me for a bit first”.

I was really starting to feel awkward again and knew the drink was doing her talking. I needed an exit strategy. She was looking fit though, I will give her that. Maybe it was her tight clothes, or maybe it was because we’d just socialised together properly for the first time that evening. Either way, her sassy mode meant I was definitely seeing her in a different light.

But right now, that light had an air of stubborn/fragile drunkenness. A state that put me on edge, as I was sober. I was exhausted and really just wanted to lie down, but instead told her I might make tracks and head home. I was obviously fine to drive so there really wasn’t need for me to kip there. I went to get my overnight bag whilst telling her I’d had such a good time etc. “No”. She said abruptly. “You’ve not had a good time and I’ve been a shit friend – abandoning you for most the night before making you drive me home”. She was being irrational but her mood had dramatically switched to a sad one. “I’m sorry” she said.

I mumbled some platitudes but she wasn’t having any of it. She wouldn’t let me speak and instead just rambled on about not wanting me to drive again, with it being so late and me surely being tired. She repeated what she said earlier about lying down with her for a bit. I probably should have just said yes at that point as I think she would have fallen asleep pretty quickly if I just lay next to her for a while.

But it felt weird and our friendship wasn’t there yet. I too can be stubborn when I am trying to do the right thing.

So I told her I’d give her a hug but I didn’t want to fall asleep by accident on her bed and I really liked the look of the sofa. But she looked even sadder and started to well up. “Pleeease” she said. It felt horrible but I dug in and said no. However I said I would stay over on the sofa as a compromise – the drive was something I really didn’t need right then.

Deb didn’t let up though and things got tense. I’d made my position clear to her but she seemed fixated on me going to lie down on her bed. At some point she also started saying I must share the bed with her that night. I don’t even think she gave a reason. I was genuinely starting to get pissed off because she wasn’t hearing my no. I couldn’t really have been much clearer even if I was trying to be a little diplomatic still. I wanted to avoid a full on melt-down.

Diplomacy wasn’t working though, so I decided to make a point by fetching the glass of water she hadn’t drunk. I put it in her hands and told het to drink up. That didn’t go down well. She told me she wasn’t fucking drunk – just lonely. There was then a very tiring half hour or so as the standoff continued – it really did go on, and on, and on.

Eventually, I decided I would just say goodnight and lie down on the sofa. I guess it’s true that actions speak louder than words because she basically stormed off to her room.

About 10 minutes might have passed while I struggled to make head or tail of what the fuck just happened – and more importantly what I was going to do in the morning. But Deb, as I found out again later, really doesn’t accept defeat. Just as I was closing my eyes, out of nowhere, she stormed in shouting my name and ordering me to go and lie down with her.

In those 10 minutes, Deb had properly festered and must have decided to up the determination and boss mode to maximum. I genuinely thought she might slap me as she came over to the sofa and yanked my arm to get me up. Fuck, I desperately needed to sleep and really couldn’t be doing with this shit. So I begrudgingly said OK for an easy life. She had won the argument and wasn’t worried about seeming smug about it. That pissed me off A LOT but I’d be by lying if I also didn’t find it a bit of a turn on. She’d broken my will-power and I’m not really sure anyone had done it to that extent before. My dick was twitching as she held my hand and led me to her bed.

Deb’s smugness was obvious. At least as much as her ulterior motive. She wasn’t happy with me lying on the bed fully clothed. She wanted me naked – boxers off and all. And under the sheets. For fucks sake. I wanted sleep and no drama. But I was also a 21 year old male who had just been bossed by someone old enough to be his mum. I realised at this point that I could easily find it in me to fuck her, if she continued to chip at me.

I had to pick my battles and my strategy was to get her lying down ASAP with her eyes closed. So my compromise was that I would get under the sheet but I would be keeping my t-shirt and boxers on. She would keep her PJs on. We wouldn’t cuddle/touch. It took about five minutes of horse-trading before she agreed that was acceptable to her. I lay very still – on my back – a good distance away from her in the bed. It felt so wrong. But it was cozy. After a minute I started to drift off.

Just as I was falling asleep, I felt her hand on my chest. Then the hand slid down to my groin. My cock quickly hardened underneath my boxers and I felt her acknowledge it with a squeeze. It felt like a truce handshake but involving my cock. I didn’t respond as I had no more energy. We both just lay there in silence. I probably fell asleep 30 seconds later.

I woke up a couple of hours later. The room was lighter and I could see Deb was still fast asleep on her side, facing away from me. I had morning wood. I felt like I’d done as much as I possibly could the night before to be respectful. But I felt taken advantage of a little, even if that seemed a weird thing to feel as 21 year old single guy. I started to panic a bit so decided to sneak out of her room and leave.

I quietly gathered my shit up and went to the kitchen. I drank some water then wrote Deb a note, using a notepad next to her phone. “Hope you’re ok. We should talk. I’ll be back at 3pm. X”

It was 7am – I’d maybe got 2 hours sleep but felt like I needed 20. I figured I’d go straight to bed at home and get a few more hours kip before driving back to clear up things with Deb.

5 hours later, I was feeling more human. I’d had 4 or 5 more hours kip before waking about Midday. I lay in bed and played everything from the day before over in my head. I masturbated and then repeated thinking about everything again. Post-wank clarity is definitely a thing.

I came up with a plan and decided on how to execute it when I went back to Deb’s. I jerked off again in the shower and then got dressed in my work clothes. I had some breakfast for lunch and then gave my parents a heavily edited summary of what a great night I’d had but how I just couldn’t get comfy on Deb’s sofa.

I set off out again and arrived at 3pm, on the dot, back at Deb’s place. I was sweating and my heart-rate was well up, despite the air-con in my truck. I decided I should stick to my script, whatever happened. I was going to take a huge gamble but my intuition told me it would be worth it. If I was wrong, I’d be in a world of pain. My dad would need a new P.A. and I could forget getting paid for the work I’d done in Deb’s basement.

I knock on the door and Deb quickly opened it. We said hi – both looking sheepish – and I gave her a warm hug. I then looked her in the eyes and said “I think you need a toy boy. I can be that if you want?”. “I’m being serious”.

Deb looked at me in shock. Her mouth opened but no words came out. I smirked at her and braced myself. Holy fuck, what had I just done?!

About 10 seconds later (it felt like minutes) Deb leaned towards me and gave me a kiss on the lips. There was no tongue but it was good. 5 seconds later and without saying a word, she grabbed my crotch. I was about to reach for her breasts but before I could she’d dropped to her knees in front of me.

I stood there like a statue, in silence and in shock of myself and what was going on. Deb undid my belt and pulled down my jeans and boxers without saying a word. My heart-rate was through the roof and I was paralysed. If I’d wanted to speak or stop her, I wouldn’t have been able to.

Deb held my cock in her hands. It was only at half-mast which I put down to the nervous excitement, terror and masturbating twice less than two hours earlier. I was genuinely terrified and excited in equal measure. Scaroused maybe. She started kissing it and it quickly grew to it’s full 7 inches. It had been too big for my ex GF to deepthroat, but not Deb.

After a few licks she took it in her mouth and got it nice and wet. I was even more paralysed. She took a breath and so did I. She looked up at me to make eye contact then took me right to the hilt in one gulp. Fuck. Jackpot.

This carried on for a couple of minutes and at some point I must have made a move to take my trousers and shoes off. We were still in the middle of the entrance hall. Deb helped me keep my balance as I untangled my feet, before going back to my cock. She looked up at me again and smiled. She asked if I was ok. I giggled and said great.

I told her I don’t usually orgasm from blow jobs. This was true and it had nothing to do with Deb’s skills. Deb, as we learned earlier, was a determined bitch when she wanted to be. She told me to hold her head and move it how I liked. Shiiit. I’d never had a girl, let alone a MILF say that to me before. It was intimidating but I did as was told.

Deb took my whole length again. Up and down, only a small hint of a gag reflex. I cautiously held the sides of her head with both hands and moved her head to my pace. Deb occasionally looked me in the eyes and eventually my legs started to buckle. This wasn’t her first rodeo and I was getting a demonstration of how age and experience would suit me well. She seemed determined to prove the point.

My god it was great.

To be continued…

Source: reddit.com/r/gonewildstories/comments/lfexlo/i_m_was_the_21_year_old_help_she_f_was_the_39