The Eye of the Beholder – Chapter 1 [MF][Masturbation]

**If you’re not into reading a long story and just want to get straight to the action then this might not be for you. **

Chapter 1

Jay walked down the street in the darkening sunset with all the approachability of a brick wall. He was staring out the ground, his dirty blonde hair long enough to hang in front of his face. Combined with the headphones blaring music into his ears his appearance practically screamed “Leave me alone!”. Aside from his unapproachability Jay was anything but extraordinary, he was just shorter than average, 24 and was slim without seeming skeletal: a perfectly average looking young man to the casual observer. Personally, Jay liked it that way, not sticking out was a relief where someone can get on with their own business and not be stared at, nor interrupted. He stared at the reflective black screen of his phone and looked at the slightly distorted reflection of himself, frowning. He had never had a particularly chiseled face and puberty hadn’t rectified it for him, he had a button nose, mouth with lips that were slightly too large, rosy cheeks and long lashes that covered a pair of blue-grey eyes. Overall, a young-looking face that couldn’t grow a proper beard, definitely not the appearance of the masculine hunk he had been hoping for when he was younger. Nevertheless, he wasn’t unattractive however his insecurities and unapproachability contributed to a social isolation that was almost entirely self-imposed. That said, Jay enjoyed his own company and amused himself watching the spontaneity of others online, daydreaming of imitating their creations himself.

Getting frisky with my gf while her sister sleeps next to us [MF]

This just happened over the weekend, and I’m still mildly in shock.

So, a bit of context: my (M22) gf (F21) and her family where taking a trip to the beach over the weekend and invited me along. There where only two rooms, a master bedroom which my inlaws shared, an a room with two bunk beds in which we sleept. The arrangement, at least to the eyes of her parents, was that my gf would sleep on the top bunk, I would sleep underneath, and my gf’s sister (F18) would sleep on the bottom bunk next to ours. My sister in law is very chill about us, so my gf told her she would sneak down to my bunk during the night, which she agreed with no issues whatsoever.

Now a small description of them: my gf is absolutely stunning: brownish-blond hair, hazle eyes, slim figure, small breasts, petite waist, huge ass, and slim legs. She is 5’2, barely 100lbs, and super kinky. My gf’s sister is pretty much her clone, except she is a bit taller (5’4), with a smaller ass and less waist line.

Now back to the story.

Picnic was a lot better than expected with wife and sister-in-law [mff]

**TLDR: Wife wanks me off while her sister watches and masturbates too.**

**Boring prologue**

The wife and I decided to make the most of the exceptional hot Easter weather and have a picnic over the park. While we were getting ready to go, her sister Kate phoned and before long was invited to join us.

I would have much preferred to spend the day fucking Kate but now she is loved up with a fella, the wife insists she is out of bounds. See my previous posts for my sexploits with her. Anyway, we were soon over the park walking to a quieter spot away from too many kids and large families. Luckily families tend to stay close to the carpark because of the amount of shit they have to have with them and also access to the toilets.

The night train [Public] [First time]

Sophie was nervous. She’d never been on an overnight train across the country before, or even traveled this far by herself. She’d assured her protective parents that she’d be fine heading up to her cousin’s house alone a week before the rest of the family joined them. She wore comfortable clothes for her journey, tracksuit pants and a loose t-shirt. No bra and a thong that was a gift from a girlfriend she could hardly feel, she was essentially in her pajamas, with the addition of some thick socks and cozy trainers. Her auburn her was in a high ponytail, and she’d opted not to wear any of her subtle jewellery, under her mother’s guidance.

Watch out for the quiet ones: My Tryst With a Married MILF [MF]

“Sorry, your reddit content is a little bit too much for me:)”

I had invited someone who had posted on my local r4r page to check my Reddit content out and judge if I fit her criteria to meet up and have good ol’ fashioned sex. Alas, ’twasn’t to be. To cheer myself up, I was reminded of “*Some days you’re the pigeon, some days the statue*”. Today, I was decidedly a statue.

A few days later, however, I see an orange envelope. A message from her!! She said she tried and liked the coffee shop I had alluded to in my earlier message as a meet-up spot.

“*Her post is wildly popular, why did she choose to write back again to me? Must investigate!*” ran my internal monologue. Not wasting any time, I offered to buy her my favorite drink from said shop. She didn’t say no.

Leading up to our meeting, I sussed out that she

– is one hot MILF who is breastfeeding

-would love to be deep-throated

-loves the idea of sex in a public place

“*This is too good to be true. If she turns out to be an organ harvester, it would still have been worth it*”

Lesson One

“We are going to go slow”, he said, in that unmistakably masculine voice that just made her catch her breath every time he spoke. “I don’t want to break you on our first night together.” *NO! BREAK ME!* She heard his words, even understood them, but she knew what she could take. And what she wanted. And what she wanted was to be his. Completely. Totally. She wanted to be every fantasy, dream, lustful idea, and dirty thought he had ever had. She was more than prepared to take him to his limits, and maybe even push beyond.

“The first rule I have is that you will wear, or not wear, anything I tell you by the time play begins.” He said. He was seated on his sofa, fully dressed from his day in the office. She had just brought him his preferred bourbon on the rocks, and was now kneeling at his feet, back straight, paying rapt attention to every word he was saying. “The second rule I have is that when you have earned your collar, you must wear it at all times, when at home. If you are very good, I will get you a collar to wear out.” He sipped his bourbon, and watched her. She was slowly trying to grind against the floor, and he could tell she was beginning to get antsy for more IMMEDIATE attention.

A new fetish of mine to explore

I’ve been in a dead bedroom for almost 6 months now with my boyfriend of two years. It’s exhausting, I’ve tried everything from begging, giving him space, losing weight and doing my usual routine that I once had that filled me with confidence. At this point I had given up, I couldn’t even convince him to let me give him a blowjob before bed anymore.

Through doing the things I used to do, I ended up dressing differently and being more active on sites like Reddit, flaunting what I knew others would crave and wouldn’t take for granted. As I did this, I had posted a few nudes on r/gonewild. I had my fair share of messages I clearly ignored, but one in particular stood out to me. He was very handsome and could sweet talk like a gentleman yet the way he worded the things he wanted to do to me sent chills through my body.

Out of town massage – (mf)

My was is very sexual. She loves to fuck and we have an awesome sex life. However, she has a conservative, church-wife like, exterior. I have brought up sharing her before and she immediately dismisses it. She is a stay at home mom who seems to be pretty straight laced. However, I knew what she was really like back in college.

So I thought I would see if the closet slut was still in there and kind of tested it out. I gave her a relaxing shopping trip for her birthday like 5 hours away and told her to have a fun relaxing weekend away from the business of the house and kids.

I set up an in room massage for her at her hotel. Told her I used the soothe app but really found a guy online and told him what I was thinking. Had him play it off as a legit massage but to see if it went anywhere more than that.

My first time with a woman was also my first threesome [FMF]

Scroll down to the bolded text for the steamy stuff, but there is a good amount of sexual tension-y exposition leading up to it, if you want the full story. ;)

I met the love of my life, Daniel, when I was 18, and we fell hard. I knew I wanted to spend my life with him. But it wasn’t until after we got together that I began to think…maybe I was bisexual.

I remember I would have insanely sexual dreams about girls in my classes, I’d wake up with my panties absolutely soaked. I used to think that you’d meet a person you were attracted to and if it was the opposite sex it meant you were straight, and if it was the same sex it meant you were gay. I began to realize that sexuality doesn’t work that way, and I was somewhere in the middle.

I began to panic that I’d never get to experience what it was like with a woman. Daniel and I talked a lot about it, I needed to know if I actually was actually sexually attracted to women, or if it was just a fantasy. I said I wanted to do this with him and we’d figure it out together.

The picnic blanket [MF] [Outdoor]

I watch as you settle onto the picnic blanket. As was your habit, when you have the chance, on a nice sunny day, you find a comfortable spot and strip down to your undies and get some sun. I always loved those moments, seeing you feel free and relaxed. Plus I love seeing your naked body: the curve of your hips, your smooth skin, the way your breasts sit when you lie on your back, the milky white parts that barely get to see the sun. Plus I know that the chance to be that naked in private but our in the open air tends to get you feeling amorous.

Being cursed with skin that only has two settings: fair or burnt, I don’t enjoy the exercise of sunbaking very much, but do like to encourage you and enjoy the opportunity to watch you. But on this day, after sitting and watching you, and feeling myself become aroused just at the sight of you, and then my thoughts of you, I decide to at least come and keep you company for a bit.