Avery here again to share more experiences Matt and I have shared together, while he was my platoon leader, and since I’ve gotten out. Yes we’re still together, yes he knows I write here. Please keep negative comments about our “inappropriate relationship” to yourself….I’m not in anymore, he’s dating a civilian girl now (me). I’m always open to feedback about my writing! I want you, the reader, to enjoy as much as possible!
Just a bit of a refresher since it’s been awhile…I’m on the petite side of life, slim, with an olive complexion, dark brown hair, fairly perky if tiny B Cup breasts, and small, dark brown nipples and I shave everywhere (:
About a week or so after the military ball that Matt teased me with a thumb pressed against my butthole, and I hinted that I wouldn’t be opposed to exploring more, we were over at his house after a long week at work, just watching tv in some comfy clothes. Him in some Ranger Panties and a tshirt, me in one of his sweatshirts, a sports bra, and some dark green cotton panties….like I said, comfy not pure sex goddess.
Matt and I are talking and he brings up that I had mentioned I wasn’t opposed to trying more things with my butt. Slightly nervous but not entirely opposed, I said “I wouldn’t mind a little more than the other night “. He asked if I would consider trying something now, down here on the couch, and again I said I wasn’t opposed, still nervous as hell, but at the same time, feeling the beginnings of arousal deep in my core at trying something new.
Matt runs upstairs and returns with a bottle of lube we keep upstairs in the nightstand and motions for me to lay across his lap. I oblige, pulling my panties down, keeping his sweatshirt on for warmth, and laying face down across his lap with my toned, firm butt facing up, completely exposed to him.
I spread my legs slightly as I feel his fingers work their way between my legs, my arousal growing as attention to my clit increases. Soon I feel pressure against my other hole as a thumb presses against my entrance. I moan gently, and then there is a sharp intake of breath as a drop of cold lube lands squarely on my butthole, causing me to squeak and pucker slightly.
Sion I feel that glob of lube being slowly massaged into my butthole, as I begin to relax, and the first inch of a finger begins to slip inside this new found entry. I grind my pubic bone against Matt’s leg as he soon has an entire thumb worked into my butt, with copious amounts of lube, leaving me feeling fuller than I’ve ever felt.
After a few minutes of fingering my hole, I can feel Matt’s rock hard arousal beneath me and I cautiously ask if he would like to try to fit it in. He pulls the finger out of my butt, which closes back up, but not all the way, as I feel a residual stretch from all the play of the last few minutes.
I kneel on the floor, leaning forward and resting myself on the seat of the couch, while my lubed butt is completely exposed for Matt. He adds a ton of lube to himself, and reapplies some to my hole, before lining up his head against my entrance. I feel myself slowly start to relax, as I mentally release each muscle of my sphincter as he slips deeper into me little by little.
A lot of lube and a lot of patience later, Matt is all the way inside my butt and I can barely move from the sensation of being so incredibly full. Matt asks if he can try to move, and I cautiously oblige, pressing my palm to his thigh to give myself some signal to him to ease up.
He begins to rock in and out of me, excruciatingly slowly as I adjust to the sensation of a cock moving in and out of my butt. Gradually, I relax into it and motion for him to increase the pace a little as I reach between my legs to rub my clit, as his firm hands grasp my waist to pull himself ever deeper into me.
As my pleasure from my masturbation builds, I relax even more, urging Matt to increase his pace until he is unequivocally fucking my butt. No other word for it. It is primal and fully about individual pleasure as I rub myself close to climax and he pushes himself into me, completely using my tight hole for his pleasure.
Within a minute or so it seems, I feel him swell even more inside me, before releasing a huge load of cum, deep inside my butt. This helps me find my own release in our shared moment of passion. With a few more thrusts, Matt has emptied himself in my butt and I am utterly spent in my own release. I feel like such a slut. I’ve tried this forbidden pleasure and although the act itself doesn’t “get me off” per se, the aspect of mutual masturbation using my clit and butthole to achieve individual release is both wildly erotic and slightly invigorating.
My confidence is through the roof as Matt pulls out of me, and the largest load of cum I’ve ever felt begins to leak out of my butt and run down my leg. I am absolutely “that girl” to my man and it’s an amazing feeling. Matt kisses me like I’m the only girl he ever wants or needs, before leading me upstairs to shower and clean off.
While anal sex isn’t a go-to thing for us (lots of time, prep, and mess), it isn’t something I’m opposed to, and is something I’m inclined to bring out for special occasions where I really want to switch it up. My one bit of advice…go slow, and when in doubt, add more lube!
Again, I’m always open to constructive feedback! I really hope you enjoyed!
♡Avery
Source: reddit.com/r/gonewildstories/comments/ogvk3v/myf_first_experience_with_analwith_my_platoon
All of your story’s are amazing. Good job.