Holly's Re-Discovery Pt. 04

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Pleasing Holly-Part 4.
3.3k words
3.02
4.6k
6

Part 4 of the 4 part series

Updated 06/11/2023
Created 03/30/2022
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I can't begin to explain this day. It has been absolutely amazing. My sexy, normally conservative wife has turned me into her personal sex toy. I've been made to do anything she has wanted. I've masturbated in front of her, for her enjoyment. Then licked my cum off her beautiful body, and with my full of my own cum, I licked her hot cunt and ass however she wanted me to. Although she was totally in control, and I was somewhat being humiliated, it was hot. I must admit, I loved every minute of it.

Holly is beautiful. I am truly the luckiest guy in the world. We have been married for over 20 years and are both in our mid-forties, but Holly still looks much younger. She has kept in great shape. She has piercing blue eyes, firm tits, a sexy ass, and her shaved pussy is perfect. I love licking her whenever and wherever she wants. However, on this day, she took complete control of me. I was only allowed to touch or lick her after I had cum for her, and she made me put on a show for her.

"You've done great today my slut," Holly said as I came down the stairs. "I told you earlier that you are going to have cum for me and please me five times. By my count we are going onto to number four. I am going up to change clothes, we are going out to do some quick shopping.

"This might be the best yet," Holly said with a devilish smile.

Holly came back down about 20 minutes later. Her hair and make-up were done and she had on a summer sundress. She looked so hot.

We got into the car and headed into town. I had no idea where we were going.

"Since you been such a good slut today, we are going to get a new sex toy. It is something I have always wanted," Holly stated after a few minutes of driving. "Do you like that idea?" she asked.

"Yes, definitely. What do you have in mind?" I asked.

"I was hoping you'd ask that. I am going to pick out a strap-on. Something that has a vibrating end that goes inside me, and then another end to use on you!" She said this very matter-of-factly. Like it was no big deal. "You remember those times that I would use a dildo on you. I could tell you liked it so much. You used to beg me to fuck you, moan so loud, and cum so hard. Well now I am going to have my own 'cock' to fuck you with, and I am going to get some enjoyment also. What do you think of that?"

At first I didn't know what to say. It was true that she had used dildos on me before, and I really did like it, but I didn't expect her to want a strap-on.

"I think it's great, if that is what you want," I replied.

"Oh yes, that is what I want. But is it what you want, do you want me to fuck you again? Make you my bitch, use your body, make you scream and cum all over? Tell me you want it, or you aren't going to get it. Beg for it!"

I honestly did want that, I was so turned on, my cock hard as a rock. "Yes, I want it. I want you to fuck me."

Holly continued to drive. "What do you want me to fuck you with? Tell me you want me to fuck you with my big cock."

I had no choice, and I did want it. "I want you to fuck me with your big cock."

"Good slut now take out your cock and stroke it while I drive," Holly replied.

I took out my hard cock and stroked it while Holly drove. It was about a 20 minute drive. Every time we passed a car, I try to cover myself, and Holly would just laugh.

The entire time, Holly kept encouraging me to stroke myself, but she kept telling me not to cum yet.

"Now when we get there, if you really want this, you need to ask the salesperson where their strap-ons are."

I nodded that I understood as I was stroking my cock. I realized this was part of the fun for Holly. She liked to humiliate me a little bit, nothing extreme, but still embarrassing.

When we arrived, we got out of the car and started walking toward the door. I had to tuck my raging hard-on in my waistband. Holly giggled and said "you're such a good slut for me. I love you."

"Anytime. I love you too," and smiled back.

When we walked in, we were welcomed by a petite 20s something female salesperson with several tattoos and piercings. "Hello. Welcome. Anything I can help you with?"

I didn't hesitate. "Yes, where are your strap-ons?" I asked clearly. Right when I asked, the salesperson looked from me, to Holly, and back again. She had a smirk on her face. It was clear that she knew what it would be for.

"Yes, we have several. They are right over here" as she led us to a wall with several different strap-ons in different sizes and colors. "Let me know if you need any help?"

Holly jumped in and asked. "Yes, do you have any that also go inside the wearer. Maybe something that vibrates?"

"Of course," The girl was very knowledgeable and pointed out several that had an end for the person wearing the strap-on to have pleasure also.

After looking for a few minutes, Holly picked out a clear strap-on that had a 5 inch vibrating end with remote settings that could be inserted into her, and a 7 inch cock that was used for thrusting. Holly smiled and looked very pleased with her new toy. I must admit, I was excited for what was in store for the rest of the night.

I bought the strap-on, and as we were leaving the saleslady told us to have a fun night with our new toy. Holly responded, "oh we will! He'll be my bitch tonight!"

I was definitely a little embarrassed, but also turned on. My cock was hard the whole time in the store.

As soon as we got into the car, Holly drove to an empty part of the parking lot and opened her new toy.

"I just can't wait. I have to know how it feels." Holly rubbed the toy in her hands and had an excited smile. She quickly reached under her sundress and pulled her panties off.

"I'm going to put this in me. Then I'll have a bigger cock than you." Holly giggled.

"You know what I think I'd like?"

"What?" I responded.

"I want blowjob. Yes, I want you to give me roadhead. I want you to suck my cock as we drive home. Just imagine, I'll be driving down the road, passing truckers looking down while your head is under my dress with a mouth full of my cock"

I didn't think my cock could get any harder, but with that comment, my cock twitched.

Holly spread her legs slightly and slowly she inserted the end of the strap-on into herself until it was all the way in. She grasped the cock end and began to stroke herself and moaning. Then she turned on the vibrations and her moans became louder, and she stroked the cock harder.

"Okay, I'm ready. Get over here and suck my cock." Holly giggled. "I've always wanted to say that."

I bent over so my mouth was just above her strap-on. She pushed my head down until my lips were on the tip.

"Open up and start sucking me!" she commanded.

I did exactly that. The cock slipped past my lips and into my mouth. I had never done anything like this before, so I didn't know exactly what to do, but I just went up and down with my lips putting pressure on the 5-inch end that was vibrating inside her.

"Oh, that is good. I am sure it will get even better as you get more practice. I bet you can go all the way down." Just then Holly thrust up into my mouth. It surprised me and I gagged slightly. This just caused her to laugh.

"Okay, I'm going to drive us home. Tell me what you are going to do as I drive."

I took my mouth off her cock for a moment and said, "I'm going to suck your dick."

Holly laughed, "Good!" Then she pushed my head back on her cock and flipped her sundress over my head and began to drive. I think it was a good thing that I couldn't see what was going on around me or how many cars we passed. My head was under her dress, with my mouth full of her strap on. Holly continued to drive as I sucked. I tried to take it deeper and push down harder, which she seemed to like.

"Oh, that is a good slut. Take my cock deep in your throat. Don't worry no one can see what you are doing with your head under my dress. Well not unless I do this." Just then she flipped her dress up so my whole face was visible. She just looked down and smiled with my mouth full her cock." Then she flipped her dress back down and continued to drive. She drove the rest of the way home moaning and encouraging me to suck her.

We pulled into the garage, and we hurried inside. Holly instantly stripped and told me to remove my clothes and to go upstairs and lay on my back on the bed. As I was hustling upstairs I heard, "Oh and start stroking that cock."

I got upstairs and did as I was told. I was naked and stroking myself hard, when I heard Holly coming up the stairs. She was naked with her strap-on cock hanging out in front of her. She was carrying a tray with shots of tequila on them.

"I think I am going to like having the biggest cock in the family. It feels so good in me, and this thing is huge," Holly said laughing as she put down the tray and stroked her cock a few times. "Since we aren't going anywhere for the rest of the day, I decided to bring tequila. I think we are both going to need them for what I am planning to do to you."

This made me a little nervous but also excited. I continued to stroke my dick as Holly came over with two shots. "You're going to need two shots for every one of mine. Open up! But do not stop stroking your dick. I want to see that cum"

I opened my mouth as I continued to stroke my cock. "Salud! "Holly said as she poured the first shot into my mouth, and I swallowed. I continued to stroke as Holly climbed on the bed with the second shot. She straddled my chest so her strap-on cock was resting on my chin. I opened my mouth for the second shot, and Holly moved up slightly so the tip of her strap-on rested on my bottom lip, then she slowly poured the tequila into my mouth.

"This is such fun," Holly snickered as she reached over and downed her shot. "Ok, now it is time to make you cum. Let me tell you what is going to happen this time. You are going to stand up and stroke yourself into these shot glasses. Catch everything you can, because what you don't catch you will have to lick up. Then, you are going to get on your knees and suck my cock until I cum. If you do a good job, occasionally I will give you another shot, but of course it won't be tequila." Holly laughed. "Oh and remember my rule, no swallowing until I tell you. One last thing, this isn't going to be a nice slow blowjob, no it won't really be a blowjob at all. It's going to be a face fucking. Yes, I am going to use your mouth and throat for my pleasure, you'll gag just like those girls do in those porn movies you watch, but now you get to see how it feels."

I got to my feet and knew what was expected. Holly sat on the edge of the bed, and I started to stroke my cock in front of her. She just looked up at me and smiled as she played with the vibration settings on her new toy. Each time she changed the settings she moaned slightly. It was clear that she liked the control she had.

"Come on stroke your cock, hun! Are you going to cum for me? You going to fill these shot glasses aren't you?

"Yes!"

"Yes what, what are you going to do?

"I am going to cum in those shot glasses."

My cock was dripping and Holly grabbed two shot glasses and held them front of my cock. I continued to stroke my cock.

"Come on, cum for me baby. Cum so I can fuck your face!" Holly snickered.

That is all it took. My cock began to tremble, I was ready to explode, but since this was my fourth orgasm of the day, my cum did not erupt, but instead poured out of my cock and directly into the waiting shot glasses beneath.

"That is perfect, just how I was hoping," Holly said as my cum pooled into the two shot glasses. "Come on squeeze that cum out!" Holly commanded.

I stroked my cock hard a few more times until the last drop fell into the shot glass. In all it was almost two full shots of cum. I knew what was in store, but I wasn't at all repulsed. It was like Holly had trained me to be her slut. I just fell to my knees.

Holly looked down and laughed, "Wow, what a perfect slut. You just dropped to your knees. You ready to get your face fucked?"

Without waiting for a response Holly stood in front of me and started gently smacking me in the face with her strap on. "Open your mouth, see if you can catch it."

Holly continued moving her strap-on back and forth across my face smacking me firmer, but never letting me get the end in my mouth. Then she firmly grabbed my head and thrust her cock into my mouth. She pushed my head down on her cock, not giving me a chance to adjust, my eyes began to water and I gagged slightly. She just laughed and pulled out, only to do it again. Drool began to escape from my mouth clinging to her cock and my lips. Over and over she fucked my mouth. I could tell she loved the control.

"It's not so easy, is it?" She taunted as she fucked my mouth. "Okay this time you are going to swallow it all. Open your mouth and stick out your tongue slightly, relax your throat."

I did as I was told, and Holly pushed her strap-on into my mouth. She held the back of my head as she pushed down. I almost gagged, but relaxed my throat as she continued to push my head further down. I felt her cock go down my throat until my face was pressed against body.

"You did it! You are my slut, you just deep throated me!" Holly snickered as she held me for a few seconds. Then she let go of my head and I pulled back. My eyes were watering, and my drool was everywhere.

"I am so proud of you, you deserve a reward. Open your slut mouth" Holly laughed as she grabbed a shot glass full of cum. She held her strap-on just above my open mouth and poured the shot full of cum into my mouth. "One shot down, one to go. No swallowing, yet" Then she returned to fucking my mouth with long strokes, each time going all the way down my throat.

"You've got this figured out. Now stick out your tongue for me." When I stuck out my tongue, she started smacking my tongue with the strap-on. Each time a mix of salvia and cum stuck to her cock and then returned to my outstretched tongue.

"This is fucking hot, I love the control. Time to really fuck that slut mouth of yours. Lie on the bed, on your back. "

I got on my back on the bed. I expected Holly to straddle my chest, but instead she stood at the foot of the bed, just beyond my head.

"Slide back until your head is just off the bed. I am going to fuck your mouth until I cum, and it's going to be deep down your slut throat."

I did as I was told, and slid back. My head tilted back as it was just off the bed. I looked up to see Holly's cock coming forward and I instinctively opened wide. She pushed her strap-on past my lips and kept going. I could feel it pass my gag reflex and straight down my throat. She began fucking my mouth like I was her personal slut. My eyes were watering, but my cock got instantly hard. This is something Holly noticed.

"Oh, look who likes to have his throat fucked. Your cock is hard again. You are even more of cheap slut than I thought you were. Stroke your dick as I fuck your mouth."

I grabbed my cock and started to stroke it, the whole time Holly was thrusting in an out of my mouth. I'd gag slightly, my eyes watering, but Holly just kept fucking my mouth. She was moaning and calling me her filthy bitch slut. Then she slid up so that her ass was directly over my mouth.

"Lick it, lick my ass, slut." She bounced up and down on my tongue as her strap-on bounced up and down and smacked my neck. I could hear her adjusting the vibrations to full power, and her moans became louder. "Yes, lick my ass, make me cum. I am going to cum." Holly yelled as she pushed down harder on my face. Just as she was about to explode she raised herself up and stroked her cock just over my mouth. As she exploded in orgasm, she poured the last shot glass of cum, right on the tip of her strap-on and into my waiting mouth. Then she pushed her cock deep into my mouth and down my throat once more, holding it deep in me. Finally, she pulled out and looked down at me with a devilish smile.

"Good slut, stop stroking yourself. I want that final load saved for the finale. Open your mouth wide, let me see what a slut I made you."

I opened my mouth wide open. I am sure my face was smeared in a mix of salvia and cum.

"You are a filthy slut. Gargle it! How does it feel to be used like one of those whores in those movies you watch? I think you liked it. Tell me you liked it!"

I tried to tell her that I loved it, but it was just a garbled mess with my mouth open and full of cum.

Holly laughed, "you can swallow, you were a good bitch!"

I swallowed and told her how much I loved being used by her, and how much I loved her. We both lay down on the bed and cuddled. She told me that she loved me tremendously and loved that I trusted her to act out on our fantasies together. There was no where I'd rather be than with her.

Holly smiled and chuckled slightly.

"What?" I asked.

"Well, that was four, you still have one to go, but I'll give you a few hours to recover, but you best be cleaned, showered, and ready by 11 sharp. Oh and that plug should be deep in your ass!"

I knew what was is going to happen! I'd definitely be ready.

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4 Comments
26thNC26thNCalmost 2 years ago

Worse with every chapter of this non LW story.

iammweaseliammweaselalmost 2 years ago

So how soon until you go all cuck on this?

If two people enjoy this, good on ya, but generally these go straight to cucksville on the bullet train. So either you'll be watching her being fucked while you diddle yourself with a butt plug or you both will be enjoying a man soon.

I'll leave this right here so I can reference back to it shortly for everyone.

AnonymousAnonymousalmost 2 years ago

Simply awful

WhackdoodleWhackdoodlealmost 2 years ago

Wring category: Gay male has it’s own place and LW isn’t it.

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