[Part 1](https://www.reddit.com/r/gonewildstories/comments/9tp8oi/my_roommate_and_i_gradually_went_from_drinking/)
**Part 2**
Tag: Anal
Circumnavigation, pt.1 (NSFW, mf, romance, oral, autobiographical)
Circumnavigation, risking it all
Prologue
Note: This series is autobiographic, the events are true as I can get ‘em to memory, but it’s been 22 years and a few details may have run together. It’s long and takes a while to pick up steam, hopefully not too boring ^_^
In 1996 I was active duty Navy and assigned to my first ship, a guided missile frigate home-ported in Mississippi. I was 23 years old, happily married, full of myself and from what I could tell, at the start of a successful career.
I had already completed one deployment to the Middle-East and had the obligatory “Sailor experience” under my belt of wandering from bar-to-bar, sampling food from cafes and street vendors, shopping in bazaars and boutiques in Barcelona, Haifa, Hurghada, Massawa, Djibouti, Manamah, Dubai, Muscat and Marseilles.
Through all of that I maintained my marital vows and thought myself all the better for it. I had been tempted, tested and tried numerous times and escaped with my virtue unscathed. I wore my fidelity like a crown and secretly judged my shipmates who failed the test. *Sigh* The higher the pedestal, the farther the fall.
Tee (NSFW, crossdresser, CD, mm, oral, anal)
“Tee” is very special to me. Our relationship started after my first deployment to Afghanistan and my first experience with a trans person. I suppose I had a whole new world opened up to me sexually, one where the sex wasn’t defined by gender roles, but rather the connection and passion alone. The “equipment” used was meaningless!
Aria was unavailable due to incompatible schedules and I had duty at the base again. The base was in the next town over from where my family and I resided, so I was confident that my extracurricular activities were safe from being discovered (I was right about this too, which allowed me many more experiences than I’ve been able to have since).
Once again I placed an ad, but this time specifically seeking a transsexual. I stated that I had my first experience and wanted more. Tee answered my ad, but stated up front that she was a full-time crossdresser. No hormone therapy and no intentions of physically changing genders. She had a prosperous beauty salon business and lived, dressed and existed as a woman.
Aria (NSFW, first time, trans, tg, autobiographical)
It all started when I had returned from my first deployment to Afghanistan.
Nothing bad had happened to me or anyone I knew while I was there, but knowing you could be blown up or shot dead without warning, at any moment had an effect on me, I didn’t realize it until I got home.
Basically, the little voice in my head that told me I shouldn’t do things to allow myself to have fun because of some moral abstract had turned off. I guess the thought was, I could have died at any moment, and there were a lot of things I had denied myself… I guess I no longer wanted to deny myself!
I was 38 years old and married with children. Life at home and life in the bedroom was very “vanilla.” Nothing to complain about, but nothing to write about either.
I had duty at the barracks on base, basically a senior person needed to be present to keep an eye on things in case something happened. They gave you a room to stay in overnight, and the next day it was someone else’s turn.
A country summer, Part 6 ~END~ (NSFW, golden showers, anal, mf, tg, mm, incest, transgender, gay, MILF, GILF)
An insistent tapping on my shoulder dragged me out of a sound sleep. I came to the awareness that I was literally stuck to Grandma! That and I had also drooled on her in my sleep, which was sort of funny.
“Honey, honey, wake up.” Grandma called. “Honey, I gotta pee, and I’m not going like that on this bed!”
Oh, shit, it was painfully funny as we peeled ourselves apart. My cum covered face had adhered to her chest, my cock was glued to her thigh! Fuck! That hurt! And I’ll be damned if it wasn’t the funniest thing that’s happened to me in a long time!
I followed her downstairs to the bathroom, trying to massage feeling back into the arm that had been pinned under her. She left the door open and I followed her in. she rolled her eyes at me as I sat cross-legged on the floor before her as she sat on the toilet, but she indulged me by spreading her legs wide, offering me an unimpeded view of her evacuation. There was no effort, no strain this time, a strong, solid jet burst forth, fine flecks separating from the main stream as it plunged melodiously into the commode.
A country summer, Part 5 (NSFW, golden showers, anal, mf, tg, mm, incest, transgender, gay, MILF, GILF)
*
After freshening up, I found her in her bedroom, the door slightly ajar.
“Knock-knock,” I said, rapping lightly on the door frame.
“Enter,” was the quiet reply.
She was sitting up in bed, above the covers with a large pillow behind her back and another under her knees, her legs bent over the pillow and stretched out before her. The skirt of the nightie was bunched up at her hips exposing her legs and I made a show of trying to look up the skirt, but her thighs were together and there was nothing to see but her cuddly belly roll.
“Ooo, you’re a cheeky little devil!” she feigned offense, but didn’t move a muscle to cover either her legs nor her fat nipples, obviously outlined beneath the opaque satin of the thin garment.
She pulled off her reading glasses and set her book beside her and gave me a thorough once-over, top to bottom and back again. I did my best to flex my abs and thighs, then raising my arms in my best “Austrian Oak” imitation.
“Turn around love,” she said, humming to herself. “Mmm-hmm, oh so nice. Back up please.”
4 A country summer, Part 4 (NSFW, golden showers, anal, mf, tg, mm, incest, transgender, gay, MILF, GILF)
*
The next morning I wandered downstairs to find the house empty and a note on the kitchen counter explaining that my grandparents had to take a friend to Pendleton and would be gone until late that night. I was on my own for breakfast and dinner, lunch would be out at the state park with the other side of my family.
“Not a bad thing,” I thought. “Maybe some time to cool down was a good idea.” Thinking about recent interactions with Grandma.
I got dressed for the park in a tank top, swim trunks and sandals then grabbed an old pair of creek-shoes from the laundry room. Creek shoes were just old worn out tennis shoes you wore in the creek with no socks. Getting soaked and drying out made them stiff and good for nothing else, but protected your feet when wading and swimming in the creek. I had left a pair here a summer or two ago when visiting with my family.
Going to the limit with an anal toy 28[M]
I learned early on that I had a thing for anal play when I was young and accidentally slipped a soapy finger up my own ass in the shower. I was shocked that it happened and more shocked that I enjoyed the way it felt. I was even more surprised, years later, at how much I enjoyed it when a friend I’d been experimenting with asked me if he could fuck me. After a disastrous first try, we did it again and I couldn’t believe how much I loved it (no details on that here, as we were in high school–hee hee).
So a few years ago, I decided to indulge my own love of anal penetration privately and set out to buy a butt plug to play with on my own. Admittedly, I got greedy with my first purchase and bought one that was way too big. At it’s base, it was probably six inches wide. The first time I lubed it up and started to slide it inside me, I could tell I’d been overly ambitious.
Revenge
**Revenge**
Disclaimer: Please note that I am german and just want to write down my phantasies, whereas the English used ith the story might not be 100% accurate. Also please keep in mind that this is largely a sexual story. Reader discretion is adviced!
With that being said: Please, sit back and enjoy the story :)
When life gave me lemons, I fucked it in the ass! Because that’s what you’re supposed to do!
And trust me, life really loves to give you lemons.
Let me give you an example: Imagine you see a beautiful young girl. Blonde, wavy hair slightly over shoulder length, maybe 1.70m tall, slim figure but really nice curves, and a face of an angel, small lips, pointed nose, plucked eyelashes, blue eyes and every smile is sweet like honey, with her small dimple on each side of her cheek.
How could this girl, no sorry, this angel be of any harm to you?
Well, allow me to introduce Aennie Klain, the nastiest and sharp-tonguedest girl I’ve ever met.
I don’t know why, but for some reason Aennie loves to expose people, especially the losers and weak ones.
First time anal with a long time girlfriend [MF]
During my final year in college, I met and began dating Jackie. She and I hit it off immediately. We were into the same bands and movies, and shared a similar sense of humor. It also helped that she was adorable. She was 5’4″ 120 lbs. Dark shoulder length hair and hazel eyes. She had some curves too. Only a 34B up top, but her ass was PHAT! I grabbed at it every chance I could, and she would tease me relentlessly with it too.
Once we graduated college, we found jobs in the same area and got an apartment together. Most mornings and weekends were spent lounging around where she would be in a t-shirt and a thong, wiggling her ass around trying to get me riled up. Most times it worked for sure. I was always 100% honest about my desire to fuck her in the ass, but she would always say “I’m sorry, baby. No.”