[FF] [anal] The Best Bet I Ever Lost (part 1) (long)

Ok, so! My weekend. Wow. I’m just now not quite so sore.

First, I’ll post our descriptions again so you don’t have to dig to get a visual:

Me: Hi! 5’0″ (wife says I’m actually closer to 4’10’, but fuck that bitch and her lying tape measure! 5’0″!), 36D-30-40, hair midway down my back, still bright anime red. Gonna prolly go back to blonde when this fades. Brown eyes. 21 years old.

Wife (Jade): 6’0″, 40F-30-44, long jet black hair down almost to her butt, hazel eyes that sometimes just turn brown on me. Dunno why. Haven’t figured out the pattern. It’s freaky. 34 years old.

So, it all started Friday night, before the snow rolled in. We had all our supplies (food, candles, toilet paper, lube, you know, the essentials) and we were snuggled up by the laptop browsing on Adam & Eve for what our next extra $50 was gonna go to.

At some point, for no reason whatsoever, Jade tells me that when I use a vibrator in her ass, she usually orgasms from it.

I’m like “No fucking way. Not possible. It’s a mindgasm, not a real orgasm.”

So we bicker, and try to find websites, and it all comes back inconclusive. So we agree to crowdsource the answer in r/reallesbians; is this a thing or not?

We also made a bet. I was so confident that I was gonna be proven right that I said if the votes went against me as of 8am, Saturday, I would spend our snowed-in day letting her prove to me first hand that anal orgasms were possible, by whatever method she wanted to prove it. I might shoulda been more specific. Hindsight.

What I woulda got is totally irrelevant, cuz I lost like a bitch. Like a *bitch*. I think I had like three votes to her 432, or something crazy stupid. I was super shocked.

So I grumbled off to take a shower while she “thought about the best way to do this” with a troubling little gleam in her eye. She’s such a sore winner. And I was totally about to be a sore loser (<- that’s a pun! :D ).

When I got out, I threw on my comfy sweats and my Adventure Time tank top, and wandered out to the front room where Jade was sitting with the laptop. She’d changed into a tight black miniskirt and a red halter top.

(Historical note: It’s the same outfit she wore on our first ever date, and it was prolly the moment I fell totally in love with her, cuz up to that moment, I’d only seen her in sensible office clothes.)

Anyway, she’d been putting together a playlist, and she looks at me and gives me this really sexy, devillish grin I’ve never seen on her before. If I hadn’t been so grumpy still, I prolly woulda melted.

“Why are you wearing clothes?” she said. “Strip.”

I’m all like “Geeze, you won a bet, that doesn’t make you boss of the world!”

“You said ‘by whatever method I choose’. I choose bossy and dominant.”

I huffed. “That’s so totally not what I meant! I’m the Domme!”

She’s all like “That’s what you agreed to. Now ditch the clothes. But.. slowly,” and she grinned even bigger, and started the playlist.

Now normally, she’s got a couple of go-to music lists to accompany sexiness; Hozier, or Jethro Tull, or if she’s feeling high-energy, it’ll be Chili Peppers. That’s not what came out of the speakers. What came out of the speakers was the opening riff of Nine Inch Nails’ *Closer*.

I raised an eyebrow, and started to worry. But I hadn’t started stripping yet, cuz except for special occasions like the last story (where, if you’ll remember, it was hard for me to keep a straight face), I’m awful at being submissive. I’m kinda a brat. I kinda need to be tamed.

Jade crossed her legs and looked at me, and kinda quirked an eyebrow, like “Well?” Well. A bet’s a bet, even if I didn’t quite phrase it right. I sighed, and rolled my eyes, and pulled my top very not-slowly off over my head.

Jade stood up and walked around behind me. She put her hands on my hips and leaned over and whispered “Slowly.” It was a very commanding whisper. I’d never heard that tone of voice from her, and my grumpiness kinda leaked away a little bit. I started to wiggle out of my sweats, and she put her hands over mine and very gently controlled how fast I could take them off. I was starting to get a little short of breath, actually.

Part of that was nervousness. Confession: my ass is sacred. Before this point, the place the sun doesn’t shine was completely virginal. I mean, sure, in the past a girl might have put the tip of her pinky in, during other stuff, but it wasn’t really anything I can specifically recall. So yeah, I was kinda nervous. My exit-only policy was about to fly out the window.

So anyway, I stepped out of my sweats, and turned around and just stood there, trying to keep an annoyed look on my face, while she looked at me. Like, *really* looked at me, like she was drinking me with her eyes. She did that for a good little while, until it started to be uncomfortable. I think I might have been blushing. Then she came to me, wrapped her arms around me, and kissed me like she was completely in control. I was all like *’Where the hell did this come from?’*, and I wasn’t in the mood to be sweet, so I kinda resisted the kiss a little at first, just to be bratty. I was still sulky.

Then she yanked my hair, and pulled my head back, and kissed me more roughly. I was shocked. I didn’t think she had a dominant bone in her body until the stuff that happened in the last story on New Years, and even then I figured it was just a small bone in her wrist somewhere maybe. But there she was, pulling my hair (hard!) and forcing her tongue past my lips (hot!) and I felt myself getting super wet.

Jade broke the kiss, and looked me up and down again, and said “You’re beautiful. I love you. You’re going to enjoy this, I promise.”

I still wasn’t sold on the whole ‘Jade gets to Domme today’ thing, so I was all like “Well, we’ll see,” with major grump in my voice. I thought she’d get mad, or sad, or something, but she just laughed and said “Yes, you will. Get on your knees and bend over the ottoman.”

I lollygagged a little, but ultimately did as I was told, and she came up behind me. I didn’t know what I expected, but I know for 100% sure I was totally not expecting her to slap my ass with her hand, so I jumped way more than really necessary. I was about to go “OW! Hey!” but just as I opened my mouth, she spanked me again! So all that came out was “EEP!”

She spanked my ass a few more times, until it felt hot, and I was back to being annoyed again. I was all like “What the hell was that all about??” Jade came around in front of me and looked me in the eyes with this sincere, loving smile.

“I hypothesize that it will help to get blood flowing to the area first. It’s all for science.”

I gave her side eye. It… kind of?… made sense.

“Stay there,” she said, and she went into the bedroom, and came out with the box of toys. My old collection got ruined, so everything we’re using now fits in a smallish box that my stand mixer came in. She set it down on the floor in front of me and took out the bottle of lube (Good Clean Love – HIGHLY recommended!) and the little narrow vibrator. It’s a pretty standard model, not very wide, about four or five inches long, nothing fancy.

Volbeat’s “Seal the Deal” was playing by now, and I’m not sure I was digging her new playlist, and I was starting to get really nervous. It kinda dawned on me, as she started putting lube around my asshole, that this was really going to happen. She was totally going to go through with it. I was about to lose my ass cherry over some stupid bet that was prolly rigged somehow anyway.

She musta noticed that I was kinda freaking out a little, cuz she stopped and leaned over me. I felt the fabric of her top rubbing against my back, and she whispered into my ear. “I love you baby. It’s ok. I won’t hurt you. If you’re scared, I’ve got all day. We can work up to it.”

I noticed she didn’t say “It’s ok, we can call it off if you want.” But I wasn’t about to be the pussy who’s all like “I take it back! I welsh! I renege! I’m a frightened little sissy with a precious, gold-leaf-plated asshole!”, so I said “No, I’m fine. Bring it on,” with, like, what I will choose to believe was a lot of gusto and bravery. I am a brave toaster.

She nibbled on my ear, and I heard the vibrator start to hum. “Relax,” she said, and then she touched the tip of the vibrator to the inside of my crack. Not gonna lie; I started getting really wet at that moment, even though I kinda flinched a little.

She kept talking, low and soft, into my ear, as she rubbed the vibrator around my lubed-up nether regions. “The way I see it…” rub rub “is that I plan to show you lots of ways that anal stimulation can bring you to orgasm today. But we need to start with a baseline. You should see how it feels without any other stimulation, just by itself.”

“Isn’t you domming me kinda another stimulation?” I asked. I’m a brat. “Haven’t you kinda already tainted your experiment?”

I felt her kinda shrug on top of me. “Heisenberg Uncertainty Principle. It’s a real bitch.”

Then she slowly pushed the tip of the vibrator into my ass. I kinda thought she’d stop with just the tip, and let me warm up a little more, but instead she used a soft, steady pressure and slid it right in. I expected it to hurt, but she’d used a ton of lube, and it was mostly just… really filling. Uncomfortable, I kinda clenched up a little, and wanted to raise myself off of the ottoman, but she was on top of me pinning me down and I couldn’t go that way. So I just groaned as she slid the vibrator in as far as it would go, and then she let it stay there for a bit.

It never stopped being quite so uncomfortable, but it also started to feel kinda good. Then it started to feel pretty good.

“Uhh… uhhh…” was about all I could say.

She nibbled on my ear again, and pulled the vibrator most of the way out. “I love you baby,” she whispered, and then slowly slid it back in.

I felt like I must have been soaking the ottoman, I was so wet. She did the same thing about five or six more times, saying “I love you” every time it was all the way in. I wanted to say “I love you” back, but I kept gasping and kind of mewling and it was a little hard to get a full breath. I was so wet, and so turned on, that I could smell myself. I was also kinda sure I could smell her too; and that’s when I realized this was turning her on as much as it was me!

She started going a little faster, but still gentle, and I lost it. Fuck me, but I actually felt an orgasm coming on. I held back, cuz I still didn’t wanna be proven wrong, but goddamn. She went a little faster, and then I was moaning for real, and pushing my ass back against her as much as I could, and I felt my thighs getting wet either from excess lube or from my pussy juice, I couldn’t tell.

Then, as she was pulling it out, with like just a tiny bit still inside, she stopped. I whimpered.

“Beg me,” she whispered. That bitch! I just kind of whimpered again, and tried to move my ass to get that thing back in me, but it didn’t work.

“Beg me.”

Fiiiiiine! “Please, put it back in me,” I groaned.

“Tell me you love it.”

“I love it! Please put it back!”

“Call me ‘goddess’,” she said. Seriously? Uurg! Ok, ok!!

“Please, goddess, put it back in me! I love it!”

“Tell me you want me to fuck your ass.”

“Please goddess, fuck my ass!” I was so frustrated, I think I more growled that than anything else.

Jade giggled. “I love you baby,” and then she pushed it back in.

I fucking came. HARD. Vocally. I heard her giggle again, and she started going really fast, and goddamnit, I fucking came AGAIN.

She kept going, and I was just wild. It was the weirdest awesome feeling. It wasn’t the same as when I cum from her licking my clit while I’m riding her face, or when she uses her fingers on me, and I dunno if I’d say it was ‘better’, but it was really good and just different.

Finally, she stopped fucking my ass, and left it in there vibrating, and kissed my neck. “I love you baby. I told you so.”

“I love you. Fine, you fucking told me so.”

“You know, I’ve got all day. You’re going to be an ass whore by midnight.”

“You’re totally pushing it,” I said. She pulled the vibrator out of me with a wet kinda popping noise, and I whimpered again. I felt empty. I didn’t expect that.

“I hope so. I’m going to be pushing you all day.”

So yeah, we did a whole hell of a lot more that day, but this is super long already and I’m fucking wet again. If I try to keep going, I’m just gonna explode. So stay tuned for Part 2.

Source: reddit.com/r/gonewildstories/comments/5na9a2/ff_anal_the_best_bet_i_ever_lost_part_1_long