NSFW story — Page 434 of 11466 — collection of stories you shouldn't read at work

[FM] Drilling McDaddy (A Pegging Tale)

On a warm August night last year at my favorite inn on the north side of town, I gave my new FWB McDaddy a proper buggering for the first time.

McDaddy, just separated from his wife, had recently achieved silver fox status in my eyes due to some cosmetic improvements and was really starting to enrapture me. Yes, OK, he was still in a state of long-term unemployment. And yes, he was temporarily homeless too. But hey, at least he looked good, had weeknight availability and was adventurous too! I wasn’t in the market for a husband after all, just a fun fuckboy.

And fortunately for me this particular fuckboy was down for some pegging.

I was pretty amped because 1) I find pegging to be empowering AF and 2) I already owned a designer harness that I’d used on just one other person at that point.

My harness was shimmery and sliver and had a fur lined interior. I’d bought it at a sex shop in D.C. so whenever I wore it, I felt like a leader of the free world understandably. And I was especially excited to see how it would look with the hot pink dildo McDaddy had brought with him that trip. Read more »

[F] Realized my love of painal

For a few months in 2018 I was hooking up a guy I had met on Bumble. I’ve always been attracted to personality and vibe more than if the guy was “hot or not”, but he was very conventionally attractive. Tall, fit and a cute face, and later found out a big thick cock.

He would come over, we would chill for about 30 minutes and then hook up. He’d never been with anyone who was willing to try anal before, because of his size. I volunteered to give it a try. I’d only done it a few times before, and guys much smaller than him would struggle trying to squeeze in. So I figured it would be best to do some prep work before he even got there (which I’d never done before). In the shower, I started fingering my ass, and realized why it had always been such a struggle. It hurt my finger more than it hurt my ass lol.

I tried using just my fingers, but it was useless. So after the shower, I took my slimmest dildo, some lube and tried to make it work. The tip to the dildo was skinny, so putting it in initially wasn’t too hard. The hard part was actually getting it inside me. But I managed. It was so tight, I’d wondered if it had hurt partners in the past. Read more »

[MFF] Playtime at the Beach with my Girlfriend and Her Friend (Part II)

[Part I is here](https://www.reddit.com/r/gonewildstories/comments/10wvk55/mff_playtime_at_the_beach_with_my_girlfriend_and/)

So there we were, my girlfriend Lisa and I, with her little friend Gina sandwiched in between us in a big hotel room shower. The girls were naked from the waist up, just wearing bikini bottoms. I was still in my swim trunks, but they were getting uncomfortable from my cock trying to poke straight out and being impeded… mostly because I had just had my mouth all over Gina’s little tits as Lisa held them from behind.

The awkward, but delicious, tension we had been building all afternoon on the beach was now completely gone as we all knew what we wanted to happen. Gina had let us know how much she wanted to play with us and Lisa had told her how much she enjoyed watching me with her. I couldn’t believe this was happening for a second time… my girlfriend was letting me play with one of her friends and it made her incredibly horny to let me. Read more »

[F] At the mall, I “assisted” a virgin friend.

I have a male friend who is a virgin. I’ve known him almost my entire life. If you haven’t guessed from previous posts, I’m the polar opposite of him. I have an overactive sex drive and am naturally a sex positive individual.

I’ve always been a big jerk to him. Mostly because I know it turns him on, but I also know he won’t do anything about it. I honestly enjoy watching him become overly excited and sexually frustrated. I’ve previously used handjobs to help relieve his sexual tension. I’m a tease, but I’m not a blue balling asshole. That’s just a cruel thing to say.

We were sitting in the mall’s parking lot. I’d eaten a pot edible about 30 minutes before, so it was just getting started. We were just sitting there chatting when I noticed his gaze drifting to my chest and legs. It’s no surprise that when I go out, I dress quite promiscuously. I enjoy the attention.

I started teasing him by squirming in my seat. Lifting my dress, moving my hands around my thighs, flirty eye contact, and lip biting. Basically, all the signs one would exhibit when wanting to “fuck,” lol. Read more »

[M] I sat and watched a friend get their big clit hard for me.

I went to see my sister and her wife the other day. While I was there a friend of theirs turned up who was transitioning from female to male. Although he wore men’s clothes and had a mans short haircut he still looked very feminine even with patches of 5 o’clock shadow around his chin.

He had been on hormone therapy for some time as is due a mastectomy in a few weeks but seemed extreme due to him being quite flat chested anyway. He is hoping for his genital reconstruction soon after.

It was interesting to hear how he made the decision and all the things he has had to go through to get this far. I was fascinated with how his body had changed due to the hormones. He said his voice had deepened but it was still quite light to me. There was the obvious increase in hair growth on his face but he explained it was now thicker on his arms and legs. No chest hair though. He said the most noticeable change was his clitoris. He said his was already quite big but now he could play with it like a little dick. Read more »

After the hot tub

“Come on Kitten,” Daddy says as he steps out of the hot tub, grabs a towel, and holds his hand out to assist me.

I watch the steam escaping from my skin as I raise my body from the protective heat and I am fully exposed to the chilling winter night air.

Daddy wraps my wet, naked body in a towel and guides me inside.

Once dry, he leads me to the bedroom and lays me down. I turn my head and watch as he grabs my favorite feather and sits down on the bed next to me.

My full body is already relaxed from the hot tub, and now, with the soft and caressing sensation of the feather against my skin, I am surrounded by pleasure.

I feel my pleasure rise again as I feel Daddy’s hands on my legs, gripping firmer and firmer as he moves his hands higher and higher…

When I lived at home I would fuck my neighbor any chance I got [MF]

He was a sexy older man in his 40s, and I used to be friends with and hook up with his son. I liked to take advantage of their pool, and that’s how things got started. I noticed him checking me out in my bikini, and I liked his attention. I started to wear smaller bikinis just for him, and eventually I would just sun bathe topless. He came outside one day while I was topless and made a comment about my tits. I started teasing my own nipples while he watched, and I took a risk and reached for his cock. When he didn’t stop me I gave him a blowjob. I even let him cum on my tits. After that we would fuck every chance we got. It went on for a long time until I eventually moved out.

How I lost my virginity to a girl who caught me masturbating in the woods. Chapter 10. Crystal and I get a weekend alone. [M/F 18]

After Crystal made us dinner, we ate in front of the fire, on top of a coffee table, while watching a movie on the TV.

“I am bummed your parents come back tomorrow. I like living with you, Crystal.”

“Don’t talk about it…I don’t want to think about you going home.”

“Well, at least they get back late in the day.”

“I am going to see if they will let us have a sleepover sometime.”

“That would be awesome.”

“They know we are having sex, so I don’t see what the big deal is.”

“Your dad is not pleased that we are having sex.”

“Well, he is going to have to get over it, because I plan to continue that activity with you…” and she leaned over to kiss me.

We cleaned up the dishes and snuggled up on the couch under a blanket, watching the movie. Crystal started leaning on my shoulder, then she moved her head into my lap and then I heard her adorable little snoring. I looked down and she was sound asleep. I think the adrenaline had worn off from her saving me from the icy pond, plus all of that physical exertion, and she was out. I was feeling very tired too, but I did not want to wake her. So, I turned off the TV and carried her upstairs. Read more »

All About Her Part 8 [M18-F41] [Cuckolding]

I must admit I was surprised at her even considering anal play since that had been a non starter for me. Mags could tell something was up, lifted her head and looked at me. She was an expert at reading me. My body had involuntarily reacted and she could feel the tension as she rested on me. “I can stop right here if you are uncomfortable with what I’m sharing with you. You wanted to know everything and I’m willing to describe everything we physically do for each others pleasure, but if it’ too much….” I cut her off. “You know I’ve always been understanding of your needs, it’s just that I thought the rules of penetration that apply to me would apply to everyone you sleep with. In all our time together you have never allowed me to….” Mags sat up and placed a finger over my lips. “You didn’t give me a chance to finish what I was going to say. Shall I continue?” She smiled. I took her hand in mine, returned her smile. “In for a penny. In for a pound. Sorry. Please continue.” Mags’ head returned to my lap as she picked up where she left off. Read more »