Tag: Reluctant

[M]y first MTF trans hookup that opened Pandora’s box.

After creeping for a long time I’ve decided to start sharing some of my sexual escapades. For my first few posts I’ve decided to reminisce on my early experiences with MtF trans women.

For as long as I can remember, I’ve had a kink for trans women. Something about a beautiful woman with a good cock has always interested me. This interest never took on more than the occasional porn search or jerk off session when feeling extra horny and the regular stuff wasn’t doing it.

Fast forward a few years in my early 30’s, I found out I was moving to Hawaii and I was being warned that Hawaii had a very large transgendered population. After arrivingI jumped on dating sites, message boards, kik etc. and noticed a larger open population of trans women oin most of the apps and dating sites. Before long, my horninesss and curiosity got the better of me and my porn searches became reality;I specifically started chatting with and searching for trans women. After a few weeks of chatting, trading random pics, and trying to make a connection I got a promising direct message; she saw that I had mentioned I was new in town and was looking to meet up, but had never been with a trans woman before. We talked about what I wanted to explore what I was open and comfortable with. Things progressed and we eventually traded pictures. Holy shit she was smoking hot. Thin, Hawaiian, tan with a perfect round ass and perky tits. I couldn’t believe it, I hit the jackpot. Our chats quickly turned dirty,e flirted and exchanged videos and pictures over the next few weeks. Read more »

My most adventurous few days [FM] [FM] (long)

Almost a year ago I wrote here about my first cheating experience:

[https://www.reddit.com/r/gonewildstories/comments/a0bqgp/my_first_indiscretion_fm_cheating/](https://www.reddit.com/r/gonewildstories/comments/a0bqgp/my_first_indiscretion_fm_cheating/)

The TL;DR is that then-37-year-old, petite, professional, married Asian Good Girl me hooked up with a grad student at a conference, and I was still feeling both excited and tremendously guilty about it. Quite a lot has changed in my life since then, and maybe I’ll write more about some of that later. But for now I want to reminisce about the wildest fling I had in my single days. It was also at a conference, but when I was myself a grad student, and part of what still gets me feeling frisky every time I attend one of these things, though after getting married I never acted on it. Until last year, of course. Read more »

Today in Missy’s search for a friend with benefits…

After chatting on kik for about a week, Missy finally meets Jeff, a tall, handsome, surfer, for coffee at a shop close to her place. He’s much more handsome than his pictures (they usually are). He’s tall and slender, definately a surfers physique, with blond shaggy hair that had a touch of grey.

They engage in the obligatory small talk and agree to walk back to her place to “do the deed.” As they walk the two blocks back to her condo Jeff tells Missy about when he used to live only a few blocks away; he moved a few years ago to be closer to the ocean. Missy gives her new friend the nickel tour of the condo, finally ending in the bedroom. They kiss for a few minutes and their hands begin to wander.

Missy feels the bulge in Jeff’s shorts and she eagerly unbuttons them, letting them drop to the floor. His cock is larger than she expected; long, girthy, uncut, and beautiful. She drops to her knees takes his hard cock between her lips, she just can’t help it. She LOVES to suck cock. Read more »

Discipline and Punishment [MF] [robot] [D/S] [bd] [Mdom] [bondage] [ScFi]

Amber Quinn was a bad girl. That was an inescapable fact.

She wasn’t bad in the sense that she’d snuck out at night as a teenager, smoked pot regularly, or pocketed an extra piece of candy from her grandmother’s pantry. She was bad in the most basic sense of the word.

Amber was selfish, egotistical, narcissistic, callous, and downright mean at times. She had little respect for rules, manners, and propriety. She was excessively vain, spending at least an hour every morning on her makeup. She was also exceedingly immodest, wearing only the trashiest outfits that showed off her sexy body, which was more attributed to her mother being a former model than her dedication to good physical health. One of her former teachers once told her that she had the beauty of an angel and the conscious of a demon.

That teacher might have only said that because Amber slept with her son to steal answers for an upcoming test, but that didn’t make it any less true. Being so self-absorbed and self-centered, Amber rarely passed up an opportunity to exploit her beauty and the desires of others to sleep with her. Read more »

[MF] Petite Latina gives me blue balls

This happened a couple years back. My family had a trip planned to Florida for months. We would be gone about a week. Leaving on a Sunday and coming back the next. Around this time I was fucking around with a female co-worker of mine. A hot Latina with small perky tits and a nice fat ass. She was a year older than me. Short and fit, we would work out together sometimes. Brown eyes and long black hair. A bit of an attitude, but she was completely submissive. We would always be making each other laugh, so she always had a cute smile on her face. She was a bit loco, but loved to fuck me. We kind of had an on and off again type of sexual relationship. We just wouldn’t be able to keep our hands(or mouths) off each other after a couple weeks of no sex.

About 4 hours before my flight, around midnight. She starts texting me talking dirty, saying she is gonna miss my dick for the week and that I can’t fuck any girls in Florida. Saying she wants to say goodbye before I leave. I am reluctant, not wanting to smell like sex when I meet my parents, but she eventually convinced me to pick her up about 30 minutes before I have to leave. I was just planning on hanging out and then dropping her off at her apartment, but she had other plans. Read more »

My Sister Lizzy [MF] [MM] [FF] [Oral] [Anal] [BDSM]

PART 8

Looking down I could see Lizzy’s pussy wide open and a ton of cum poured out as it began to shrink.
“Holy Christ, that was so good, I don’t think I could do this on a regular basis but “Holy fuck” that was intense.”

As Lizzy rested, Tom managed to stand and stretch, his cock still hard as nails stood proud.
Dave and I were in awe of having watched Tom loose his virginity to the girl we loved.
What was even more amazing was that moments later Lizzy was ready again.
How did we know?
Lizzy spread her legs and asked if Dave and I would fuck her front and back.
That is a request that she didn’t have to ask twice.
Dave laid down on his back, while Lizzy mounted him. As she bent over I lubed up her ass and began the process of working my way past her little ring.
As Dave and I began to create a rhythm, Tom was closely watching the action, his face just inches from the point of our coupling. Read more »

The Massage [OC] [Massage] [MF]

Your friend Wen is training to be a part time masseuse. One day she asks if you’d be willing to let her practice on you. You pretend to be reluctant but you actually feel a surge of excitement in the pit of your stomach. You’ve always liked Wen, but you’ve never gone further than a kiss on the cheek. Now she’s going to rub her hands all over your body!

You feel a flutter of nerves as you press the doorbell. It’s like a first date! Wen answers the door and welcomes you in. She seems genuinely happy to see you and grateful that you could help out.

As usual, she’s made no effort to look nice. Her black hair is falling loosely and she has just enough makeup to enhance her natural good looks. Today she is wearing a black tee with a plunging neckline and no outward signs of a bra underneath. Her short skirt really shows off her petite figure.

She leads you into the spare bedroom. Walking behind her, you notice that her legs look amazing in high heels and you catch the sweet scent of her perfume. Read more »

[MMF] A Welcumed Stranger

I have really awakened sexually lately. I have been battling mental health issues since I was a teenager, and finally got myself feeling happy. An unexpected/wonderful side effect of this? … an almost INSATIABLE sexual appetite I never knew I had.

I have never been reserved about sex, but ever since I started feeling better – it’s made me feel wild and exited in a way that I never expected from myself.

Its just fun.I am having a fucking blast messing around – plain and simple. So much fun that it’s really become at the focal point of my life lately. I split my free-time either out on the town flirting with strangers, or Tinder trying to pic which of the 100+ sexual puns is worth responding too.

I’m doing this with one goal in mind. I want to explore some boundaries and see how far this wild feeling takes me. I’m gonna see how enjoy this new slutty me as see how far we can go with it. Read more »

Fun For All [MMMMF cuck reluc voy Mdom oral]

*A Redditor asked me to write this story about his wife. This is all fiction as far as I’m concerned.*

—

It was Friday night and Nikke was at home waiting for Ric. He never usually came this late from work, but after 12 years of marriage she could let things slide. They were a happy couple, and while Ric wanted more than Nikke was willing to provide, everything worked itself out in the end. Instead of pacing back-and-forth, worrying about her husband, she’d go about her normal routine. Her favorite show was on tonight and she hated missing an episode.

Nikke went into the kitchen and poured herself a glass of red wine. There was also beer for Ric and his friends, in case they wanted a few pints. But Nikke preferred something sweet she could slowly sip in, just getting drunk wasn’t her thing. In fact there was a lot that wasn’t “her thing.”

She came back from the kitchen and heard the doorbell. Thinking it was Ric she walked quickly to the door and opened it. He wasn’t there, instead it was his friends: Tomas, Matthew, Jason, and Ralph. Oh, right, tonight they were supposed to come over for their usual “Guy’s Night Out,” except Ric wasn’t home yet. “Come in, come in!” said Nikke as she brought them inside. “Ric isn’t here, but have a seat, I’ll make something for you.” Read more »

I invited my best friend to loose his virginity in a threesome with my gf and me [MFM]

On a school trip
>Me and my best friend share a room
>My gf comes over (we were all in the same class)
>I’m horny af so I start start kissing her, touching her etc.
>Shes reluctant because my buddy is in the same room but I convince her he doesnt mind and that it will be hot with an audience
>Things are getting hotter and hotter and I’m so horny I ask my friend without thinking if he wants to help me out.
>Hes super enthusiastic but my gf is unsure. Luckily shes horny enough so she agrees after some convincing
>We start having a threesome, he loses his virginity, we both get our dick sucked and we both bang her
>I have to cum so i release the pressure on her face (yes she was kinky)
>He continues to fuck her doggy while I sit down in a chair
>Slowly starting to feel jealous when the horniness leaves me and I realize my best buddy is fucking my gf.
>Try to get hard again so I can join again so i start jerking off.
>Suddenly the door bursts in and 7 classmates storm in. They have been watching through the lock and start laughing and joking, giving my best friend a high five and teasing me and my gf
>Shes basically sitting with my friend on his bed half crying. We all start to put our clothes on and throw the classmates out from the room.
>We talk about what happened for some time until my friend asks if he can continue because he hasnt cum
>I angrily say sure but my gf doesnt want to because shes not in the mood. She just gives him an handjob and then she leaves
>Next day everyone knows what happened
>Back home the whole school gets to know, my gf breaks up with me and changes school
>Since then Ive been known as the kid who let his best friend loose his virginity to his gf.