[MFM] How my extremely shy girlfriend ended up spending an entire weekend getting fucked by my buddy and I –Part 1–Setup, and The Sex Shop

Disclaimer: I am not into humiliation or big alpha male men claiming my gf in front of my while I jerk off in the corner. I have no issue with people that enjoy that but this isn’t that sort of story.

Me and my buddy who is featured in this story go way back, and we have a very bro type relationship. This is reflected in the way we interact with each other. The texts we sent to each other are word for word. And when my gf texts him she isn’t some sort of sexting queen, and he is trying to respect boundaries.

I’m trying to keep the story as reflective of the truth as I can. The only reason I could go on with the things the story describes is precisely because we are so close, and because I trust him.

The dynamic is that of me breaking down barriers and bringing my friend into our sex life and having fun, not that of my friend seducing my gf and her being enthralled by his alphaness. If it sounds like something you’re on board with, read away.

Part two involves a pool and a weekend of nothing but sex but part 1 begins much slower.

Setup

I’ve never shared this story before but years have passed and to this day it’s the most sexually thrilling experience I’ve ever had so I want to share it, for both my pleasure and yours. It’s a long one so bare with me.

Let’s call me Roy, my friend Taylor, and my girlfriend Natalie.

Natalie and I were high-school sweethearts, we met at 15, lost our virginity to each other at 17, and stayed in a monogamous and fairly vanilla relationship for many years to come.

At the time of our story Nat is 23 years old. She is an extremely shy girl, although she looks stunning now, she definitely wasn’t the stereotypical attractive girl growing up. She never got much attention from guys, she always kept to herself, and she is the type to hang around with my friends and play video games rather than go out clubbing and partying. Nat doesn’t talk much, especially when it comes to sex related topics, as she grew up Christian.

She always liked the goth aesthetic, she is very into heavy metal music, and she tries to look the part, which somehow seems contradictory to her Christian upbringing and shy personality, but it is what it is.

Her skin is pale and she has long black hair. She is 5.4″ and very slightly chubby in that really hot kind of way. She is rocking a juicy pair of DD’s with the nicest nipples you could ever suck on. She has a banging round ass, and she always kept a nice landing strip on her pussy just the way I liked it.

The first years of our relationship I was overly protective, and kind of the jealous type but as we and our relationship matured, and I found my self trusting her completely, I encouraged her to start dressing more sexy. Nat went through a small makeover where I pampered her with little gifts, sexy heels, short summer dresses and thongs and g-strings enough to replace all her normal underwear. By the time we were 23 Nat had flowered into someone who although was still shy, and on the cute rather than sexy side, could turn a lot of heads, and I discovered for the first time that I have a kink for it. I liked the fact that people were lusting over her, and I could tell she liked it too, although we never talked about it.

On the rare occasion that we went to a bar, she would always dress up really nicely, and we would have the best fucks later when we went home. At this point this was the extend of it though, I didn’t know what a cuck was, and I wasn’t considering any sort of threesome, much less with a friend of mine. It was just a hot little thing the two of us enjoyed.

At home Nat opened up, and the shy reluctant exterior falls apart to reveal a very submissive girl, who might struggle to dirty talk or be open about her desires, but who was an absolute slut at heart. Nat wont tell you that she wants you to put a leash on her tie her to a bed and let a train of guys run over her, but she wants you to do it without asking, and once it’s done she will thank you and fall asleep with a smile. Of course I didn’t know this at the time, I had only ever seen glimpses of it, as I never wanted to push beyond her comfort zone. But the fact that no wasn’t really in Nat’s vocabulary would soon become apparent to me, and it would change our sex life for the better.

Part 1-The sex shop

Our story begins a couple of weeks before the day we went to the pool and ended up having a threesome. Nat, Taylor, and I were walking downtown. Nat was wearing a short, black summer dress that revealed a bit of cleavage, and a pair of sexy black heels. We had just finished having a coffee and were strolling about window shopping.

Out of all my friends Nat got along with Taylor the most, the three of us would regularly hang out together, as Taylor is very easy going and fun to have around, he could get her to talk and overcome her shyness much better than my other friends could. Over the years I noticed on numerous occasions that Taylor would take peaks at Nat when he thought nobody was looking, something that I enjoyed but we never talked about it, and there was never any sort of sexual conversation when the 3 of us were together.

On this particular day Taylor was doing a poor job of hiding his glances towards Nat’s tits, and I was getting pretty aroused, so when we passed outside a sex shop I grabbed the opportunity to make something good out of our day. I stopped in front of the sex shop and the 2 of them gave me a weird look, so I said ” Let’s go have a look, it’ll be fun”

I could tell Nat immediately panicked, but to Taylor I might as well have just announced that he won the lottery, so he gave a casual “why not” shrug and moved towards the shop. Nat just flushed and stood there, so I gave her some playful tugs, and pulled her in with us. I didn’t really have any expectations going in, I just wanted to make Nat as turned on as possible to prepare for the coming night, but this would turn out to be the event that changed everything.

Walking in we were greeted by a staff member, but the shop was otherwise empty of customers. None of us had ever been to a sex shop before, so we were all kind of awkward, and tried to be quite. I held Nat’s hand and the 3 of us started browsing the wares. We did the “awkward laughing at the weird looking sex toys” dance, while pretending we’re not completely turned on by this whole thing. Taylor gave us some space, probably hiding a boner and avoiding the awkwardness, and Nat kept by my side flushed completely red the whole time, while I explained to her what the different toys were used for.

She was giving me the “I can’t believe you got us into this” look for the first 20 minutes refusing to speak a word. I was trying to get her to relax and open up a bit, and was asking her if she found anything she liked, something that she wanted to try etc. and finally after a while she pointed towards the butt plug section. I was ecstatic — a breakthrough. We walked over and she seemed really interested. I explained what they’re used for and had her pick one out. She picked a really small one, the typical steel butt plug with the purple gem heart on the back and I teased her a bit ” Are you sure you’ll be happy with such a small plug?” She nodded but I picked up the slightly larger one too, telling her it’s in case she changes her mind later, and finally she gave me a smile.

We started making our way towards Taylor who was still pretending to be casual, and she went stiff again, I had to push it to the next level. I showed him the plugs and Nat squeezed my arm but I didn’t care ” Hey man look what Nat picked out ” I winked at him, and he picked up on what I was trying to do. His face lit up and he took the bigger of the 2 plugs examining it and giving Nat a sly smile. ” Nice, ever used one of these before Nat?” . My dick was diamonds at this point. The question was asked directly to her, she couldn’t avoid it, and for the first time in the 8 years they’ve known each other they are having a conversation about sex. Taylor was asking my loving girlfriend, if she’s ever had a plug up her ass. This was going perfectly.

Nat did her best to give a casual no, but I could tell the same thoughts were going through her mind. I just pictured the juices that must be flowing down her leg and kept on going. ” So Taylor did you find anything that you think Nat would enjoy?”

“Well, nothing like that, but I was going over the lingerie and I think she’d probably find something she likes there”

Perfect, with Taylors help this was going much more smoothly now. He diverted her attention towards the lingerie isle and bid her to follow him. She let go of my hand reluctantly and followed. She looked at a few items and I asked her if she found one she really likes, to which she replied ” Not really, you pick one”. I wanted her to open up and be the one to pick and thankfully Taylor pushed her too ” Come on there must be one that you liked”. She hesitated and picked one off the rack, obviously trying to pick the one that looked the least slutty, but I encouraged her telling her it’s a good choice so I added it with the plugs.

I said I’ll tell you what, because you’ve been a good girl I’ll buy you more than one. You picked one you like, I’ll pick one I like, and then Taylor will pick one he likes too, does that sound fair? To my surprise she looked at Taylor and smiled nodding.

I picked a red see-through set, that came with a red g-string, and Taylor being an absolute hero picked the sluttiest thing he could possibly find, a black lace dress, with cut-outs for the breasts to go through. He picked some black stockings, underwear, and garter belt to go along with it. When he showed his choice to Nat, and she looked at the girl in the picture, she turned to me and I could tell she was about ready to burst right there and then.

” Do you like Taylors choice baby?” I asked. And she nodded “Yes it’s a bit much but it looks sexy”

I turned to Taylor ” Do you see a toy that could go along with this? ” I could tell he was hoping I would ask the question because without hesitation he went and brought a black bondage set, along with a collar and gag. He handed them off to me and turned to Nat for the first time not trying to hide his stare, he fixated on her boobs, and told her ” I think you’ll look really good if you’re tied up wearing that set I picked for you”

Words cannot express how exhilarating that moment was, and Nat managed to get out a “thank you”, while she was visibly struggling with how horny she was, before we started heading for the counter. I picked up some questionable blue pills off the counter too, paid for everything and we headed out.

Once outside it was time to get home, the 2 of us had an hour drive ahead of us, while Taylor lived nearby. The thought of a threesome wasn’t in my mind yet at this point, I got what I wanted, an incredibly hot experience, and I was rushing to get home and spend my night enjoying every inch of Nat’s body. Taylor, being a bro wanted to get out of our hair so I can do just that. Just before we said our goodbyes he asked her which one she’d be wearing tonight and being a faithful girlfriend she lied and told him she’d be wearing the one I picked, still naively thinking that it might bother me if she said shed wear the one Taylor picked. He gave a smile and winked, ” Well have fun then you two, this was great” and we headed for the car.

Once, in the car it was pretty dark and we immediately start making out. I put my hand under her dress and I had never felt her pussy so wet, her panties were soaked. I start fingering her and she starts moaning but some people were making their way towards us so we had to cut it short. I start the car and get to driving. I took one of the pills as I knew I wasn’t gonna last more than a minute once we got home and I wanted the night to be long. Through the whole drive we couldn’t keep our hands off each other, and now that Taylor wasn’t here she was opening up, becoming the slut only I get to experience in bed.

“Did you have fun today my little slut”

“Yes, what was that? What came over you?”

” I’ve been enjoying the attention you get for a while now and I just thought I’d start acting on it”

“What do you mean?”

“I mean Taylor. Did you see how turned on he was by you? I bet he’s already home jerking off. He couldn’t keep his eyes off your tits”

“No way, it’s not like that. Wait so you like it when he is looking at my tits?

“What do you think? Only you get to enjoy men lusting over you?”

“I don’t enjoy it… it’s just flattering that’s all”

“Oh please, you were practically dripping on the floor in there. You don’t have to deny it I’m serious, I don’t mind at all. In fact I like it. You’re wearing what Taylor picked tonight. I know that’s what you really wanted to wear”

She smiled at that and didn’t say anything.

“So now that you know that I don’t mind you can be honest. Do you like the thought of him jerking off thinking about you”

She hesitated before answering yes.

“Say it”

“I love that Taylor is jerking off thinking about me”

I rewarded her honesty with a little rub on her pussy.

“Good. You can be open with me. I promise I wont get mad over something like this”

She nodded and we spend the rest of the ride fondling each other and talking about what we would do once we got home.

By the time we got home I could feel the effects of the pill. It gave me a slight headache but I was about ready to cum as soon as we entered the door. She made to go get dressed in Taylors outfit but I grabbed her and told her to make me cum before she goes. She dropped her dress and bra on the floor revealing her perfect breasts, and after sucking my dick for exactly 5 seconds I took it out of her mouth and came all over her tits. I hadn’t cum this hard in a very long time and she gave me a playful smile.

“Good girl. Go get ready like a good little slut. And don’t wipe the cum off your tits, it looks good on you.”

She went in the bedroom and started dressing up for me while I sat on the couch and saw I had a text from Taylor.

“Man that was so hot, never in a million years did I think I was gonna be asking Nat if she’s had a plug in her ass, or what kind of lingerie she likes. I hope I didn’t overstep and boundaries”

“I know that was amazing. No you did great man, she got super turned on, we just walked through the door I already came on her tits and we’re prepping for round two. She’s dressing up with what you picked for her as we speak. I can tell you like her, I’m completely fine with it. I know she doesn’t look like it but she can be really slutty and submissive. She told me she liked the thought that you would go home and jerk off for her.”

“For real??? This is surreal man, yeah I do like her she is super hot but I know how much you care for her, plus we’re dudes so it’s hard to talk about that sort of stuff. Well have fun man don’t be wasting time talking to me go give her a good pounding”

“Wait I have an idea. I’ll try to get her to send you a picture with the things you picked for her. Maybe sext you a bit too. Talk in a bit”

“No way you can get her to do that man. We’re talking about Nat here. If you pull this off you’re a fucking legend”

“Have faith buddy”

With the new plan in mind, and a surprisingly effective pill in my system I sat there rock hard waiting for Nat to come out of the room. A few minutes later the door opens revealing Natalie, dressed in the sluttiest thing I’ve ever seen her in, tits bursting out covered in cum, collar and leash around her neck in her sexy high heels, ready to spend a night getting fucked.

I extend my hand and she walks towards me and I make her sit on my lap and start making out with her caressing her tits and pinching her nipples.

“You look like a proper slut now baby, I’m so proud of you. Did you get the plug in?”

“No I was hoping you can get it in for me”

I grabbed the leash and led her to the bedroom where she went down on all fours on the bed and spread her asshole for me like she’d been taught. I put some lube on the smaller one and with a little effort got it in her tight ass, before switching it out for the bigger one. Once she was ready I pulled my dick out and sat on the bed in front of her and without saying anything she starts obediently sucking my dick.

“Do you know what we’re going to do now baby?”

“You’re going to fuck me”

“No. We are going to send some pictures to our friend Taylor. After all he picked the outfit he should get to enjoy it too don’t you think?

She froze.

“Are you serious? No, no one else has ever seen me naked no way.”

“You said you want him to masturbate and cum for you. Well you have to help the guy out don’t you think? It’s you who turned him on in the first place, it’s your duty as a good little slut to help him finish”

Honestly any other night this wouldn’t have worked but things were different today, I saw the slightest hint of consideration in her eyes and I pressed on. I grabbed her leash and I made her stand up, then slid a finger in her dripping wet pussy, and kissed her. She gave into the kiss and put her arms around me before pulling off.

“You’re crazy, you really want someone else to see me like this?”

“Right now there’s nothing else in this world that would make me happier. Are you gonna be a good slut and make Daddy and his friend happy?”

I saw lust in her eyes, she opened her mouth to kiss me and grabbed my dick but I pulled her leash away from me. “Stand by the wall we need to give him a good shot”

To my absolute joy she turned and stood by the wall. I grabbed her phone and she was awkward but tried her best to give a sexy pose. I took a few pictures and then to my surprise she went to the bed took a doggy style pose.

“I know you like it when I do this.”

I took a bunch more pictures from different angles and had her spread her asshole to show the plug as well. Then I sat next to her and gave her a kiss.

“Good girl, I know how much you want this you don’t need to pretend you don’t.” She shook her head. I gave her her phone. “Go on, send them to him”

She panicked again “What me? No way you send them, it’s so weird to just send him a picture out of the blue”

I hadn’t told her I already talked to him about it and I didn’t want to tell her. I wanted to see her do it.

“Don’t send it out of the blue. Start a conversation, talk about today, and ask him if he wants a picture”

There was some back and forth but she eventually fired up messenger and sent a simple hey, to which she got an immediate response. I sat next to her and started rubbing her clit, not telling her what she should say, I just watched it evolve, neither of them seemed to want to push it at first but it got there eventually.

“Hey, what’s up?”

“Umm… not much I was just thinking that today was fun. I really like the dress you picked for me”

“Oh yeah it was super fun haha. Well I’m glad you liked it. I know Roy really seemed to like it, I thought you two lovebirds would be busy right about now what’s up?”

“Yeah he did. I know I said I’d wear the other one but I wore this instead. It fits really nicely. We…got a bit busy in the car and I just thought I’d text you see if it wasn’t too weird back there.”

“Not weird at all that was great. I mean I get what you mean this is far beyond anything we’ve ever talked about but I’m happy it went down to be honest.”

“Good…me too”

“What’s up Nat is there something you wanna say?”

“Yeah I just don’t know how to say it”

“Only one way to say it lol. Is Roy with you?”

“Yeah…”

“Are you “getting busy” right now Nat?”

“Yeah…”

“Oh…That’s pretty hot. Well he’s clearly ok with whatever it is you wanna say so go ahead”

“I just wanted to ask you if maybe you wanna see me wearing the things you picked out for me…”

“As in if I had 3 wishes type of scenario?”

“No…I could sent you a picture”

“Oh wow. Id be lying if I said I didn’t Nat. Do you want me to see you wearing those things?”

“Well this is really embarrassing, but yeah I think I do. Roy said… you’d be thinking about me, so I should help you out”

“Roy knows me well. Yeah I think you’re really hot to be honest, I couldn’t get today out of my mind. I’m glad you texted. I would love to see a picture of you wearing those.”

“I took some pictures for you but I suck at posing, I think they’re terrible”

“I’m sure they’re great.”

“Is there a type of picture you like? Like something specific you want to see. Maybe I can take a different one…”

“Well to get the awkwardness out of the air, I’m just gonna say it, If I could pick I would love to see your boobs, it’s why I got you a dress with cut-outs for them, I couldn’t stop staring at them all day today”

“Haha, yeah I noticed, well here it comes I guess, this is happening”

She sent a picture, face, tits cum and everything. I could practically feel Taylors excitement and at this point me and Nat were steaming. She was stroking my dick and I was rubbing her clit.

“Good girl. You can do better. Get a little dirtier with him. Treat him like you treat me. Taylor has now seen you in your sluttiest, there’s no pretending you’re not a slut anymore. Go all out baby.”

This got a very nice reaction out of her and I could tell all her walls were beginning to come down.

Taylors response comes, “WOW”

“some blushing emojis”

“This is beyond expectations Nat, I can see Roy already had some fun with those tits”

“Yeah…I’m good at making him cum. He calls me his little slut”

“Nat the little slut. I like it.”

“He said I should treat you the same…I should be your little slut too, so I hope my picture helps you cum”

“I’m already working on it. Did you say you had more pictures for me? I can’t get enough Nat I would love to see more”

“Yeah this one is a bit sluttier so maybe it will help, it’s my favorite position”

She sent the one where she is on all fours

“This is the hottest thing I’ve ever seen Nat good God. You look amazing. I never thought you’d be this kinky.”

“I’m not really kinky…I just like to please I guess”

“Well you’ve pleased me.”

“Did you cum yet?”

“Working on it. I think If I can get on more I’ll be ready to go. Do you want me to cum?”

“Yes…please cum for me. Any picture you have in mind?”

“Yeah, I’d like to see you with a dick in your mouth so I can imagine what it would look like if you ever sucked my dick”

I could tell this really hit the right spot for her, she closed her thighs around my hand and squeezed moaning loudly.

“Come on my little slut do what you do best, and I’ll send him a video of you sucking my dick”

She didn’t even hesitate to the idea she got on sucking and I took a 2-3 minute video of her sucking my dick and sent it to him.

She got back on her phone and waited for his reaction and when he didn’t answer for a couple of minutes obviously trying to clean up the jizz, she sent a message.

“So??? Did you cum?”

“Nat I came so hard I needed a minute to recover. God that was amazing. I’ll be using these for a loooong time. Thank you”

“I’m glad to hear that. No need to thank a slut doing her job”

At this point I sent him a text from mine, “Enjoy man but I’m gonna take her off you now I can’t hold out any longer.”

“LEGEND. Enough said”

“Haha good night bro”

Part one is over for the most part. After this we had an incredible night. The pill lasted a good 4 hours, and at no point of those 4 hours was I not rock hard. We fucked a lot. We talked some more she was so excited about the whole thing. By the end of the night I had jizzed on her tits a good 3 times more. I spend an hour eating her out while telling her to think about everything that happened today, her pussy was the juiciest it’s ever been, and she slept bathed in cum that night, wearing the attire that Taylor picked for her.

It’s hard to understate how arousing this was. It might seem a bit vanilla for you all but unless you know Nat then it’s really hard to explain how unlikely this whole set of circumstances was. If you told me that morning that this is how my day would go I would have laughed in your face. Nobody thinks Nat could ever to something like this. But that’s precisely why it’s so hot to me. A perfect embodiment of the closet slut.

I’ve never written a story like this before, or anything for that mater. This has taken a lot more time to write than I thought it would so I’ll have to make part 2 tomorrow. Part two involves a pool, and a weekend of nothing but sex for me Nat and Taylor.

Source: reddit.com/r/gonewildstories/comments/o8pdbi/mfm_how_my_extremely_shy_girlfriend_ended_up