For more or less, I’ve been going through a lot this last year. I’ve been struggling with depression and trying to learn to be okay on my own/not in a relationship. A girl I went to school with in another state moved to the same state as me for work, and I honestly love her. But, she is dating another guy we went to school with. I’m incredibly happy for both of them, as he has been wanting this for a long time and they deserve each other. The reason I’m writing this is because not feeling like I’m date-able/lovable has been putting me into positions where I make regrettable choices and risk other people’s relationships. AKA: My roommate.
Category: gonewildstories
My best friend let’s me check out her new boyfriend’s huge cock. [FFM]
A couple months ago I went to visit my best friend for the weekend who lives about three hours away. She just started dating a new guy who looks very hot and is really cute. She mentioned at some point that he had as really big cock and was great in bed. I said she was lucky to have found him.
I’ve been married for three years and went to visit them by myself while my husband stayed home. I got there on a Friday night after work and we talked for a little bit but ended up going to bed somewhat early as I had a migraine from the drive.
The next morning she and I were sitting in the den drinking coffee and talking. She mentioned how when they first got together she would be really sore after having sex for any period of time. I asked just how big he was and she said he was close to 10 inches. I said no way. She said yes it was and she’d prove it.
[MF] The Business professional’s view in the end [part 2.5] Long
This is a direct continuation of part 2. Plus, it spaces out the wild events from first night and the kinky hot events of the second night. However, It’s written that neither are required to enjoy this story.
Katie was texting me throughout the workday from how amazing last night was, mirror selfies from the hotel bathroom with and without clothes, to outright sexting. She was even begging me to ditch work to meet up early at one point. No, not distracting at all. Pffft! Who would be distracted by a hot woman wanting sex, in a hotel, that evening, with me? Why does my inner monologue sound an awful lot like a high-pitched Flynn Ryder, I don’t know! But I got through the day by some miracle without getting fired for permanent trouser tent. I made a pit-stop at my place to shower, pick up an extra change of clothes and grab my bedroom fun bag. The traffic was insane heading back to her Hotel but I trudged along knowing happy times were coming. Katie alerted me that she finished up another day of conference booth duties while I was over half way there. Soon, another pic of her naked body selfie looking sultry and tasty dinged on my phone. I was already annoyed at the slow traffic, hungry from skipping dinner and now horny to boot. No! not distracting at all.
How I came Out..lesbian [FF]
Since I was 12 years old, I knew I was not attracted to men. I was a lesbian through and through but society’s pressure meant I could never come out in the open.
Years went by, I dated a few men, just to seem normal, in the hopes, I’ll feel ‘normal’ but it never happened. Guys liked me, but I never felt anything for them.
Fast forward a few years and my family is pushing me to get married as I reach my 30s. I was just 22 lol
Anyway, I couldn’t do anything about it. I thought I should not fight it and maybe let them find a guy for me. They did, a handsome man, who was well-off and seemed like a catch, for a straight woman. Oh well, I married the man
However, from day one, things weren’t good. I remember the first time he kissed me and I felt gross and felt even worse when I felt his cock.
No matter what happens, I can never like the feeling.
Tying up my FWB [MF]
Backstory: I’d always wanted to try tying someone up and a submissive fwb called Anne confessed that it was one her fantasies too. So one night she invited me around so we could finally try it out.
About us: I’m 5’8 with blond hair, blue eyes and an average penis. Anne is a stunning 5’3 brunette with long, thick hair, B cups that perfectly fit my hands and cute bubble butt. We’re both fairly active we’re slim and toned too.
**Story: Anne greeted me wearing just a short, sexy robe that showed off her perfect figure. She led me into her bedroom and I set down my box of restraints next to her box of toys that she’d left out for me. I turned to find her stepping out her robe fully naked, giving me a shy smile. I pulled her close for deep kiss and then put her down onto the bed.
We started making out passionately, our hands wandering all over each other and she quickly got rid of my clothes. At this point we both wanted more and so I started off by cuffing her wrists together and then tying the cuffs to the top of the bed so her arms were kept stretched overhead. Anne licked her lips nervously as I then blindfolded her. Lastly, I attached some leg restraints (ankle cuffs with a rod to keep legs spread apart).
Watching & Hearing My College Crush Claimed By Her Black Fuck Buddy [MF][Cuckold]
A lot of people wonder how the whole cuckold fetish starts for men and for me it probably all started at the end of high school/early college when I lost one of my first crushes/loves to a black lover. I adored Sarah so much and we were amazing friends and unfortunately I always wanted more but was deep in friendzone with her. We hung out all the time, chatted online/text and we had a flirty tension with each other. She wasn’t a 10 hot, but she was your typical cute suburban white girl with nice tits, skinny body and GAP fashion sense.
White Couch Sex: A True Horror Story [M][F]
Quick backstory: sometimes with sex if the d is too long and hits my cervix. I bleed. Just a thing that happens but still gonna get it checked out.
I’d seen this guy a couple of times, we decided to get away to his cottage for the weekend. It is worthy of mention that his dads live there and he fully refers to it as the “big gay cottage.”
Sure enough we roll up and this thing is immaculate. Home decor, paintings and prints, and everything is white. I’m talking white walls white floors white couches white beds. Everything has been mostly detailed white. I gave no thought other than to the problem of the white bedsheets and to be fair, I did mention to him that it could be a problem even though In the past he’d never made me bleed. The bed was creaky anyways so we decided not to disturb “the dads” in the night and just try to avoid it altogether.
Role Play to Reality – Round 2 [FM]
Part One
https://old.reddit.com/r/gonewildstories/comments/bn6hh4/role_play_to_reality_fm_long/
I woke up to an empty bed. The lights were off in the bedroom and I looked out to the living room to see Tim on the couch in a robe looking at his phone. He looked up, smiled, and greeted me. He then told me that I had been asleep for about an hour. I got out of bed and went to the bathroom peed and wiped myself with a warm face cloth. I walked out the living room and checked my phone in my purse. No messages, calls, or emails. I slid it back into my purse and walked over to the couch. Tim offered me a robe and I declined as I snuggled up next to him on the couch. He told me that he was getting caught up on emails. I jokingly asked how many pictures he took of me when I was asleep. He showed me his camera roll and I told him I was offended that there was not even one. He laughed as I leaned in to kiss him. We kissed for a while, then I slide my hand in his robe and began gently rubbing his hardening cock. I untied and opened his robe and began kissing his chest working my way down. I started licking his shaft and could taste the remnants of our sex. I was getting turned on. I began sucking his cock and Tim fondled my breasts. His hand then slid down and he began playing with my pussy and I spread my legs to give him more access. I was immediately getting turned on and began moaning with his cock in my mouth. I came up for air panting and then went back to devouring his cock. He placed his hand on my head and I moaned as his hips gently thrusted his cock deeper into my mouth. His finger was probing my pussy and it was dripping wet. I finally separated and climbed on top of him and slip him inside of me. I began working him slowly inside of me as he sucked on my breasts. His hands were grabbing my ass and would occasionally come up and kiss me.
[F]ollowing my primal instincts with my bf’s roommate [M]
Ok, first just for some background info, I’ve been with my boyfriend for more than 3 years now and we actually have a very stable and developing relationship that we both feel completely secure in. I don’t even believe in soulmates, but feel like he is my soulmate if that concept existed. I love him more than anything in this world and would never do anything to hurt him (PLEASE keep this in mind). I repeat, I would NEVER do anything to hurt him. So with that said, I also have to mention that part of our development and growth in our relationship has been working on ourselves. Ever since we both went to a meditation retreat last year, we made an agreement to never give up on our self development, and in turn this would lead to not give up on our relationship. It basically relates to the old as time concept of “If you can’t love yourself, how the hell are you going to love anyone else?”. And speaking of love, our idea of love has been transforming ever since that retreat and our daily practice of meditation.
Laura and the quick thank you fuck. [MF]
Laura. I’d asked her out twice over the year or so I’d known her and I’d been politely rejected both times. She was out of my league, the kind of girl who could literally have anyone she wanted. Five foot fiveish, long brown hair, lithe. Big brown eyes and an Irish accent and an ass that everyone in any room stared at as she walked away.
One weekend I’m leaving the bar debating what to eat and what I’m going to jerk off to at home when I saw her, some drunken older guy with his hand on her arm, her expression one of worry.
Being the nice guy I was trying to be I walked over and hugged her, all like “there you are Laura, I’ve been looking everywhere for you”. The creep looked confused for a moment, said something sweary, looked her over one last time and stumbled away. Good deed accomplished, time for spring rolls and a wank.
“How can I ever repay you” she asked with a smile.
Sodomy. That’s what I wanted to say. I didn’t. “Easy. Go out with me sometime.” Was what I did say. She shook her head.