Being told to use a cucumber as a toy amoungst other sexual things. [F] 29 [M] 29

I woke up to a surprise on the counter of a couple notes on a cucumber saying;

‘You have to put this cucumber in your pussy and leave it in until I return. Video call me when you get up for your instuctions. You’re not allowed to cum.’

So I followed the instructions and videocalled him. He had me get up on the island on my hands and knees with my butt facing the camera while I inserted the cucumber. It was so big and solid. I was told that he was going to be sending me videos to watch, I’m not allowed to use my hands to touch the cucumber or my pussy in any way, and any Kik conversations had to be all live pictures and videos.

He started by having me put my plug in but, with the size of the cucumber it was really uncomfortable so he allowed me to remove it after a small amount of time and just use vibrating toys instead.

He moved on to instructing me to use my clamps while on the chat roulette site.
I got to see about 5 different loads on that alone?
All cumming for me.?
I was told to rub lotion all over my stomach and tits during and only use my feet to move or adjust the cucumber.

[M]y first [F]WB Made Me Cum in My Boxers, Pt. 3: How Many Pairs of Boxers Can She Ruin in One Day?

Once again, thank you all for your response to the previous stories of my quick, fun times with Haley. I’ve really enjoyed all of your comments, DMs/chats, and even awards (!!!). Sorry for the delay in posting these, I want to take my time writing them up! For those who have missed previous ones, you can find [Part One here](https://www.reddit.com/r/gonewildstories/comments/nh63ic/my_first_fwb_made_me_cum_in_my_boxers_which_led/) and [Part Two here](http://reddit.com/r/gonewildstories/comments/njidm7/my_first_fwb_made_me_cum_in_my_boxers_pt_2_video/).

Just to recap who I and Haley are, I’m Tyler. Currently 31, but an 18yo high school senior at this point. I was a late bloomer; a bit chubby until I grew into my height (6’2), and then became pretty tall and lanky. My cock is slightly above average size-wise (6.5 to 7″ if I’m really feeling it!), though I had no idea at the time that I was above average. I played baseball and was in decent shape, though the years of social awkwardness and not seeing myself as attractive had left me pretty unexperienced; I had kissed a girl, but never gotten past first base at this point. Until I started talking to Haley.

A Year of Kiss-Drunk Car Fucking (Part 2) [FM]

Part 1 is here:

[https://www.reddit.com/r/gonewildstories/comments/llcfvt/a_year_of_kissdrunk_car_fucking_part_1_fm/](https://www.reddit.com/r/gonewildstories/comments/llcfvt/a_year_of_kissdrunk_car_fucking_part_1_fm/)

*Note: This story takes place in 2019. Basically, the whole year. “Lani” is an alias.*

It’s almost her [F21] birthday and naturally I’m [M25] thinking about her again, so here’s the rest of the story so far with Lani. I described her in detail in the first part, but she’s a petite Filipina with the prettiest brown eyes and the most fuckable mouth. Imagine Honey Gold (google her) without the tattoos and you’re most of the way there. On the other hand, I’m a tall, white guy with Winter Soldier hair.

So, let’s keep going.

I thought about her every day. No one had ever made me orgasm like that before, let alone with just their mouth. We met up again months later at a mutual friend’s party. Lani wore tight black jeans that cupped her perfect little ass and a red floral print top with a collar that looked suspiciously like a choker. As everyone dove into their drinks, Lani and I caught up over a bottle of wine she snatched from the kitchen.

The Ultimate Butterface [MF]

This happened about five years ago. A girl from okcupid and I were meeting up at a coffee shop in the afternoon. I was stoked because she was very pretty and we had a lot in common. I got there on time, ordered a coffee, and waited. When a very homely girl came up to me and said she was so-and-so, I was obviously confused and disappointed.

This girl was like a 3. She had a very large nose, (I actually have thing for hook noses, but hers was tragically large) a severe underbite, no chin, thin lips, and her eyes were very asymmetrical. She was also hiding her figure under a big baggy hoodie, probably because it was unattractive too.

She was quick to admit that the pics were fake, but said the profile info was real. The pics were her friend, given with permission to catfish (her words). She told me I could leave right then, that she’d understand, but if I stayed she’d make it worth my time as long as the conversation was decent and I was okay with “banging an uggo.”

Family Movie Night [Mom][Son][Sisters][inc]

“This must be the third or fourth sex scene.” I thought to myself as the couple on screen began to undress.

My mom had suggested watching a movie together as a bonding opportunity having me and my twin sisters all back in the house for summer break.

I was starting to feel a bit uncomfortable by the film she chose though. The scenes barely even passed for an R rating and the whole thing played more like a porno than a movie. I was sitting on the couch next to her as my sisters sat on the floor.

They were both dressed in tiny night shorts that complimented their athletic forms quite nicely. Both had gotten into college on volleyball scholarships and were somewhat of a local legend for both their sporting talent and striking beauty.

As their older brother I never really gave much thought to that before, however the steamy imagery on screen was going to my head and I found my eyes wandering to them as much as the TV.

I gave mom a glance to see if she was getting nervous by what we were watching but her face showed little expression at all. However I did notice a certain shifting when the actor pushed himself inside the woman on screen.

I followed her Tumblr we became friends and she ended up fucking me over and over [MF]

I have met a lot of random people online — and many of those people have become friends in real life. I am a big fan of actual human connection and learning about new people — probably one of the big reasons that I identify as polyamorous. Amongst the people I have met I made a few interesting friends on Tumblr years ago — back when it was new, and interesting, and strange, and still very porn-y. I have had the chance to meet three of those friends over the years. One was scheduled and planned and we had lunch one afternoon and a really good conversation. The only thing that was awkward was that I called him by his screen name and not his real name because… I forgot his real name.

One wandered into a bar that I was working at one summer and looked really familiar to me. Likewise, I looked very familiar to him. He connected the dots first and asked me if I was on Tubmlr when I brought him a beer — I was shocked, but said yes — and he told me he had been following me for years. Awesome.

[M] Me and Housekeeper [F] Chapter 1

To begin, my name in this story is Ron. I live opposite countries with my parents, so, one Christmas season i decided to surprise them and go home unannounced. My siblings helped with the surprise and it was successful. Upon arriving at our house i immediately noticed this pretty house helper. We’ll call her Karen. It was not uncommon for our house to have house helpers since they help take care of my grandparents and ease the workload around the house. There were 2 house helpers, a late 40’s woman and Karen. Karen was light skinned, petite, and has a cute look on her. I honestly thought she was older than me but i was wrong.

The first time i interacted with her, it was all shyness and awkwardness since i am the son of the people she work for. Now, i’m used to doing chores around the house and her being a helper thought it was her duty to clean up after me. But i was not raised that way. So one morning after i ate breakfast, i was preparing to bring my dish to the sink to wash, when she goes to me wanting to take my dish so she can wash it on her own. We touched hands and i saw her blush. This is the first indication that she likes me.

I [M] fooled with housekeeper [F] in Xmas ’18

Firstly, all names in this story will be changed to protect all parties involved. Secondly, all acts done was consensual.

To begin, my name in this story is Ron. I live opposite countries with my parents, so, one Christmas season i decided to surprise them and go home unannounced. My siblings helped with the surprise and it was successful. Upon arriving at our house i immediately noticed this pretty house helper. We’ll call her Karen. It was not uncommon for our house to have house helpers since they help take care of my grandparents and ease the workload around the house. There were 2 house helpers, a late 40’s woman and karen. Karen was light skinned, petite, and has a cute look on her. I honestly thought she was older than me but i was wrong. The first time i interacted with her, it was all shyness and awkwardness since i am the son of the people she work for. Now, i’m used to doing chores around the house and her being a helper thought it was her duty to clean up after me. But i was not raised that way. So one morning after i ate breakfast, i was preparing to bring my dish to the sink to wash, when she goes to me wanting to take my dish so she can wash it on her own. We touched hands and i saw her blush. This is the first indication that she likes me.

My first proper blowjob!![FM]

So my last post was about how my first time went with my cousin. Nearly three weeks have passed since then and I and the cuz have fucked four times since, the latest fuck being this Sunday. The other two times, besides the first time, were not so eventful. We had basic condom protected sex both times, similar to the one described in the first post, but without any blood, and me not swallowing his cum both those times.

Me and the cuz have gotten more friendly since the hymen breaking session, even in front of my parents. But we didn’t try anything new until the Sunday yesterday.

The basic plan was the same, of course. I would go for my morning jog, skip over to his house, have sex and return. While my periods had started on Saturday, but I was insanely horny to fuck. At the same time, I didn’t want anything near my cooch. So we decided this time it will be a blowjob only.

[MF] The college boy and the mature mom (very long)

[Repost from my previous account. I’m going to put up a few of my previous posts to give context to some recent experiences.]

Should probably start with a little explanation. As I was growing up I was tall and gawky with glasses and an overbite. Then I was an athlete throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but still understand the perception of not being considered attractive.

This isn’t the first experience I had or necessarily the hottest (though I think it’s pretty hot), but the easiest to write–my first experience with an older woman, which really got me into enjoying older women. I really am into the build-up and noticing details and emotions and hope you are too.

I was a junior in college, fall semester, still living on campus. On Tuesdays my best friend and I had a large open swath of time just after 11am, so we’d usually do something together–go shoot ball, grab lunch, go to a bookstore, lift, etc. For some reason on this cloudy, early October blah Tuesday we decided to go off campus and treat ourselves to that fine restaurant chain known as Chilis. We’re seated at a table next to three women in their late 40’s, early 50’s. My friend and I order our drinks and start looking through the menu.