Category: gonewildstories

[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 »

[F] STUPID SLUT CLUB

I’m always early, which is maybe a terrible thing, but most of the time I’m on time and everyone else is running late. He[M]40 and I used to work together, so our friendship is relaxed. We’ve played D&D together before, and I know his wife 38[F]. She usually attends our sessions (playing sessions, don’t get dirty yet), and if we tell folks to arrive at 7 o’clock, most arrive by 7:30.

Exceptionally, lol.

As a result, I would arrive on time, assist with setup, lay out coasters and glasses, and clean up after myself because, as I mentioned, we are friends and I am comfortable with their home. He was engaged and later married, so I didn’t act on my suspicions of tension or attraction when we were direct employees. Never straying from the rules and always acting professionally.

Several months ago, I arrived promptly, helped set up as usual, and made a joke about how there wasn’t much to do as we waited for everyone else. As I pulled coasters out of their kitchen, I heard him enter from behind me. Again, hardly extraordinary. I need to get the whiskey and water for our game. To my astonishment, while I was choosing the coasters, he rubbed against me and remarked, “We could make it less dull,” while going for the whiskey on the shelf. 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 »

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.

I gave one last blowjob to my terminally ill neighbour ….. [FM]

This goes back many months ago, exactly in February 2022 (I was 18 by then) . I had a neighbour then who was ill for many years and late 2021 , he was informed by the doctors that he only has 2-3 months max. Unfortunately at the time, no one was there for him , he was divorced and no kids. So I used to visit him every other day to keep him company and sometimes bring him baked cookies …etc (sometimes he would be in the hospital and sometimes at home)

Until it was time for me to leave and go to my college dorm so I payed him one last visit, in which he told me he doesn’t have much left – we chatted about whatever and had a few laughs. I asked what his last wish was and I totally didn’t expect him to be that blunt, he listed a few things then said he thinks I’m really hot and anything from me would be nice …. I was a bit confused as to what does he mean by anything and he said explained what he meant Read more »

[MFF] I used a strapon to spit roast a girl with my bf

We had been on a date with her once before and it ended in really great sex with amazing chemistry. She was so sweet and seemed really reserved at first, but let loose really easily when we got her into bed. We couldn’t host at the time, so we went for drinks and then to a hotel for our second date. When we were in the hotel room, we kind of registered that we were in an adjoining room, but checked it was locked and didn’t think too much of it. After we felt more secure, we were all making out and got undressed pretty quickly. We had a lot of foreplay, with my boyfriend and me going down on her, them going down on me, us fingering her, and blowing my boyfriend together. Read more »

I sealed the deal on my first threesome! [FM]

Last night I was at her apartment again and made a few jokes about calling “Tim” again after everyone left. When the time came and it was just her and I she got out her phone and sent home the text. He responded right away. She obviously told him we had snow treats left because we got into them as soon as he arrived.

We didn’t mention what happened last time at all and all mad one more strong drink. Clearly Tim had already been drink as well so that plus the treats we were all feeling great and flirting, talking with ease.

Eventually my friend and I go to her bathroom together and she actually is the one to suggest we both come out in our underwear. She changed into a matching black lace set and I stayed in my brown bralette and nude thong. When we emerged Tim was clearly stunned but kept his cool.

I don’t remember if we exchanged any words I just know I sat right in Tim’s lap and started making out with him. We didn’t really have a plan beyond walking out. Almost immediately I could feel him getting hard beneath me. I got off his lap and got on my knees in front of him on the sofa. My friend joined me and I reached for his zipper. He actually stopped me and asked us to kiss. Read more »