Getting her into anal play and stretching her ass. [MF] Long, very detailed

Sorry it’s been a while everybody. I’ve been balancing work and applying for school which I officially got into. Tulane bound come January. Anyway, me and Brittany have made a lot of progress in the bedroom. She’s opened up and tried a lot in the 3ish months we’ve been at it. Enjoy.

Brittany is into the buttplug now. She still takes some warming up, but I genuinely enjoy all of that so win win. For maybe the last 3 weeks we’ve been testing the waters with ass play. So far her favorite is a tie between rimjob with her vibrator and finger in the ass while she’s bent over getting fucked. To quote her, “when you use your tongue, it’s like a really gentle massage in a spot I’ve never had a massage. Pretty much sensory overload” which is a pretty good way to put it. So this took place the weekend before Halloween. We had a party to go to Friday and Saturday. I teased her about the idea of wearing it out and she nervously wagered what she wins if she can manage it in until we get back home. So if she can’t do it, no clothes all Sunday for her. If she does, she has a week of on call oral sex for any reason at any time. Another win win.

On Friday night she wore it during sex and for a little while after. Kinda like a trial night. Saturday morning she wore it during sex again then took it out while she got ready. About 20 minutes before we leave, I asked if she was ready. She said “yeah, but you have to put it in” which meant I had to rim her ass. What an inconvenience to me. She’s leaning against the counter and I hike her dress up and slide her thong to the side. Her tiny little asshole waiting to be penetrated by this gold jewel plug. I jumped right into it. She got her ass licked like it was melting ice cream. I may have added to the sensation by fingering her pussy too. It was already wet so why not?

Once her body started moving to the tempo of my tongue, I began to press the end of the plug on her asshole. If I didn’t act now, we were probably just gonna end up staying home and finishing up which isn’t a bad thing, but she did do her makeup. She exhales as the thickest part stretches her open, then gets swallowed by her ass so only a little blue jewel is showing. On the drive there, she comments “not gonna lie… I’m really turned on right now. You know how I get when I drink. Im only gonna get worse.” Honestly I don’t know if that was a threat or her trying to tempt me into getting some miles in my backseat.

Now we’ve been at the party for about 2 hours and her body language is extremely suggestive. I’m at the bar talking with one of my friends and Brittany hugs me from behind with a little grab action. She had a few red bull and vodkas so she was hyper and tipsy. She pulls my down for a kiss and then gets between me and the bad with her ass pressed against me. Brittany leans back so her mouth is by my ear and says “so far I’m winning and I wanted you to know I’m enjoying it. Probably the alcohol, but yeah… feels good.” Since she grabbed on me, I reached down and squeezed her ass pushing on the plug essentially fucking her in public. Good thing it was loud or everyone would’ve heard her breathing like she was getting her ass fucked. She turned around all wide eyed with her trademark eyebrow raised and said “I probably deserved that, but who’s to say I didn’t like it? Maybe I’ll come back for more.” She walked off back to her friends and looked at me with this particular glare in her eyes that made me a little hard. Not gonna lie.

It’s about 3am when we head home. She’s pretty drunk. Still keeping it together, but noticeably drunk. I told her she could take it out, she won. “Maybe I don’t want it out? What if I want it in? What if I want… say, the bigger one?” Brittany reaches over and finds my dick. Slowly stroking me over my pants, she comments “I feel you growing. I like that I can touch you, but you have to wait to touch me.” She hikes her dries up to her stomach and slides her panties to the side. I’m completely hard now. “Mmmmm that’s better. (now she’s masturbating) I’ve been wet all night with this thing up my ass. You’re in trouble when we get home. OH! Somebody likes what he sees. Can I let him out? (Reaching up my shorts and feeling around) God that vein is huge.” I’m rushing through my neighborhood when I zip into my driveway. She crawls over the console and mounts me then starts grinding on my erection while kissing my neck. She smells so fucking good, I love it. “I’d be lying if I said I liked the butt plug at first, but it feels so good now that I’m used to it.” Now my pants have a little wet spot on them, and just as we were about to get to it in my front seat, her ass hit the horn twice in a row. We laughed it off and she jumped on my back since she wasn’t wearing shoes.

Once were inside I sit her on my counter top and slide her panties down her legs. They weren’t even dry. I could hear that jewel scraping on my counter as she leans back spreading her legs to pull me in for an obvious victory lick.

“This is the first of many that you’ll be giving this week. Hope you’re ready.”

Brittany grabs my hair with both hands and forces my face into her pussy which is glistening wet. I can feel the warmth between her thighs when my tongue connects. She lets out this sexy groan then inhaled through her teeth. Her body bends towards me and she braces herself up while I prod her sealed slit open with my tongue. I went at it hard trying to send her over the edge, but I could only hold off for so long. I stood up and drug her off the counter as her legs wrap around me. We kissed the whole way into our bedroom and I dropped her on her back. It was a little cold in my room so goosebumps scattered across her skin. Her nipples were probably hard under those little sticker things she had covering them. Brittany looks down between her legs then back at me with an eyebrow raised and I assume thinking, “well, it isn’t gonna lick itself.”

She did win after all so it was a fair assumption. Still fully clothed and harder than steel, I went back to licking. Her legs wrapped around my body and she pulled me in like she was trying to suffocate me the best way possible. A few minutes go by and I feel her tensing up. Before I could get any further she says “take off your clothes” in a very demanding tone. Once I’m naked, I pulled her dress up and over her body and peeled her little stickers on her nipples and they harden up immediately. My tongue makes circles around one while my hand grips her ass and side and in one quick motion, I made entry, slowly pushing until there was none left to give her. Her eyes closed and her lungs filled as I began pumping her pussy. We were face to face and all I could think about was how good she smelled and felt.

She giggled and looked through me with those bright green eyes biting her lower lip as I began to thrust harder. We started out slow and sensual, keeping the romantic mood alive but like two 28 year olds, that turned into fucking when the butt plug became the center of my attention. I grabbed her silver hair and pulled her head back like I was a vampire and I bit into her neck while pumping her soaking wet hole. Her legs are up and wrapped around my waist and my free hand begins to push and pull on the plug. Essentially she’s being double penetrated because I’m breaking the seal and stretching her asshole then letting it be swallowed back inside. She didn’t flinch, not even once. After about a minute of that, she tells me “get the bigger one. I wanna try it.” I said it’s a lot bigger than the small one. We can wait and keep practicing. She said back “no, I know you like it and I love that you were so patient with me. Get it. I can handle it. Really, I want it.” Fuck I love this girl.

I climb off and I’m standing next to my bed digging in my nightstand, and the angel she is starts stroking my cock. Her soft hands are teasing me. Gently dragging her fingertips up and down the shaft. I show her the next size up just so she understands that it’s significantly larger. She smiles then throws that platinum hair over her shoulder and rolls into her side with her ass facing me. Looking back at me she says “I want you to do it.” Want me to do what? “(Sighs) you know what I want.” Say it. “(Raising her eyebrow grinning) I want you to put it in my ass.” I wanted to hear her say it. I spread her ass with one hand and slowly pulled the one she was wearing out. And I mean slow. Her tight ass bends towards me as the girth stretches her hole open revealing more of the steel inside her. Once it broke through, I placed it on her hip like a trophy. It had been in there for about 6 hours. Now for the boss battle. Instead of jumping right to it and ramming it in there, I decided to show her a little attention and rim her empty asshole. She has this sexy kinda laugh/moan combo that is a huge indicator that she’s nice and eager. One finger in her pussy and my tongue piercing her ass had her body contorting and fidgeting in pleasure. And out of nowhere her hand grips my shoulder and she says very declaratively, “do it. I want you back inside of me.”

I pushed her so she’s laying face down keeping my finger inside her and applied some lube to her ass. One last time I showed it to her and without hesitation, she took it into her mouth and sucked it while looking me in the eyes. Fuck. After she finished sucking it, she licked in a circular motion up to where my fingers were gripping it. Again, fuck.

Moment of truth, the tip is pressed against her, stretching her open wider and wider until we get to the thickest part before it narrows down to the stem. She has a handful of the sheets and her eyes are wide open. Her toes curled and all I can hear is the sound lube makes and her sexy groans. I leaned down and kissed her asscheek and gave the final push. “OH MY GOD! Wow… ok, that’s… that’s a lot bigger baby. (Deep breaths) oh my god. Let me get used to it before you continue.” I told her to move around a little so we don’t find out too late that it hurts which I asked numerous times. Brittany took it. Props to her because she’s not a big girl. Quite a difference when it involves entering your, until this point, virgin asshole.

She rolled over on her back and smiled nervously saying “yeah, it’s big. Like really big. It kinda hurts, but at the same time feels good. I’m into it but be easy with me alright. This is still new territory for me.” I wasn’t gonna hurt her. Well, I went down on her for a little bit to help take her mind off of the small weight up her ass and she responded quickly. It might’ve taken 90 seconds and I felt those legs start to twitch. She likes to get up on her elbows and watch when she cums. Couldn’t manage it this time. Apparently there was a lot of build up? Jokes aside, it was a powerful orgasm. Normally she moans or huffs and puffs some barely distinguishable words. Not this time. She tensed up and her whole body hardened like stone. Her pussy began leaking and her asshole was pushing and pulling the plug back and forth like a piston. It was hitting my chin. Her abs matched the plug flexing again and again. Then, in a shocking turn of events, as her orgasm continued, she fucking pushed it out! This fairly large plug was orgasmed out of her super tight asshole. I wanted to stop and make sure I felt what I thought I felt, but she just kept going. Tiffany was like that, a drunk orgasm machine that would go on as long as you didn’t stop. Her legs wrapped around my neck trying to force me to stop. I’m way stronger than her. No dice. I pinned them back 90 degrees so she was spread open from every angle. She tried pushing me away with her hands. Strike out again. I didn’t relent at all. Her body quivered and bent until I couldn’t fight her off anymore. She boxed my ears with her thighs which kinda hurt.

Once I stopped, she was breathing like she was fighting for her life. I had to let her collect herself and I began kissing her inner thighs and pelvis up to her rock solid nipples. She continued to convulse for a few seconds while I was rubbing her body. Her eyes were wide and she was staring up at me in shock. “It hurt a little when it came out. I was trying to get you to stop because it felt like I was about to pee! Don’t laugh! You would’ve had to clean it up.” So I wasn’t about to subject her to more pain even if she could tolerate it. We had some sweet sensual moments and then once we got all the cute stuff out of the way, I rolled her on top of me facing away, reverse cowgirl. She has this habit of teasing me because she knows exactly what I like to see. Brittany lowers herself onto the tip and eases herself about a third of the way down then comes up and slides it between her asscheeks. I could’ve taken control but I liked to watch her cut loose and be the temptress she secretly is. Her fingertips drag all over my legs and stomach until she finds herself and begins massaging her shining pussy.

I was sliding against her skin colored asshole pushing with my hand to apply pressure. Once she decided it was time, she really turned up the theatrics. Brittany has one hand gripping her pale head of hair and the other is clenching her asscheek pulling it apart. Then, she raises up slowly to the head of my cock, then comes crashing down full force so there’s that wet slapping noise. “Mmmmm fuck baby. Touch me.” My hands find their way onto her hips gripping her hard body. She grabs my hands and moves them down to her ass looking back at me and blows a kiss. Yeah, that was sexy.

She starts to moan while sliding up and down my shaft. I wanted to cum so bad and at the same time, I didn’t want to stop. I could stare at this for an eternity. Once again Brittany surprises me by moving my hand down to her asshole pressing my fingertips against it. To sweeten her offer, she drops down onto her elbows so her tiny skin colored asshole it looking straight at me waiting to be entered. I circled it applying pressure and eased off. I wasn’t sure if she was hurting at all and just wanted the extra sensation, but she confirmed her wishes when she exhaled through her teeth eagerly “go ahead baby, put your fingers in my ass…” Lube was still coating her hole, I slid in with ease. She moaned as I slid all the way into her, knuckle deep. “Mmmmm god that’s amazing! Mmmmm what did you do to me… I’ve never been so turned on in my life.” She sits up and reached back to lock my wrist in place. Once she got in her rhythm Brittany began to ride my finger instead of my cock. Her pussy was just an added sensation for me. I could feel it. I didn’t know how soon, but I was on the verge of cumming.

After telling her I was close, she gets off and turns around so shes facing me. Her cute perky tits shake as she drops her weight onto me again and again. She was reading my facial expressions like a book and knew I was almost there so to help me cum, Brittany reaches down and grips my cock at the base stroking with her hand while still fucking me. Girls got serious management skills. “Cum for me. I want you to cum.” I was close but I kept holding back. I wanted to keep going. It’s been a damn good night and she’s come such a long way since we reconnected. Brittany leans down so her lips are pressed against mine breathing against me. My hands squeeze her hips and she whispers against my skin “cum inside me… I want you to cum in me. Mmmmm do it for me baby, cum for me…” She grabs my face with one hand and rubs my lips with her thumb. The other hand scratches down my shoulder and chest.

It hit me. Hard. I felt that light as a feather feeling starting at my head all the way down my body to my toes. I reached up and pulled her into me, her scent filled my lungs and I blew the fuck up. Her ghost hair dangling down on my shoulder smelled so fucking good. All I can say is it was powerful. My body locked up and I shot so much cum inside of her that she groaned in this lusty satisfaction. “That’s it baby, cum inside me. Oh my god that feels so fucking good. Mmmhmmm, all of it baby. Fuck I can feel it shooting.” I have no idea how much it was, but I had to have shot a half gallon into her. My heart was beating so hard I could hear it. “It’s leaking out of my pussy” which is the first time I’ve ever heard her say pussy. Drunk Brittany is dirty. Once I regained cognitive thought, she got off and cum dripped right out of her. A lot of it.

Tonight was full of surprises because what she did next raised the bar. She moved down and sucked my cum covered dick. The noises she made alone had me maintaining an erection. I love those wet blowjob sounds of her lips, tongue, and throat sliding up and down my cock. At this point she was just keeping the tempo. I was done. It began to soften up and her bright green eyes connect with mine when she takes the whole thing down gagging herself for a second then coming up for air and kissing up my body. We have a moment of kissing and caressing when she sits up on top of me and wiggles her hips and giggles. I grabbed a towel and babywipes while she plugged up and prevented any more cum from leaking out.

We rinsed off and got back into our clean bed and fall asleep. This whole story takes place in less than 20 minutes once we got home. The next morning I wake up first and go do my morning routine. She slept for about three more hours and when she did wake up she called me back into my room. Her head was throbbing. I got down next to her and began rubbing her naked body. In her cute little morning voice she said “my butt hurts. I think you were right about it being too much.” All in all, want a bad day despite her being sore and dehydrated. She made me go down on her twice that day. Once when she woke up and again before bed which resulted in sex. I never thought my tongue could get sore but fuck, she was ringing the bell two and three times a day. This girl is something else.

Source: reddit.com/r/gonewildstories/comments/9xs9en/getting_her_into_anal_play_and_stretching_her_ass

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