Tag: Anal

Night with sugar daddy [mf]

Sugar daddy was in town yesterday and today for work, so we met up last night. He said I’m allowed to post stories but they’ve been approved by him before being posted.

I go to the hotel he’s staying at, as instructed, only wearing a red mini dress and fishnets. When I go to the counter, I’m told I’m not on his list and can’t have a key, I have to wait in the lobby. I text him about it, about 10 minutes later, the same guy comes to me with a key and apologizes. I take the key and go. I’m told not to get naked, not surprises, no touching, just wait and watch TV. Finally he shows 30 minutes later.

I greet him at the door with a kiss, he grabs my ass and smiles. After putting his stuff down, he sits on the edge of the bed and tells me to come over. He spreads my legs a little and runs his fingers to my pussy, smiling because I didn’t wear panties. I tell him I miss him and he starts to change then gets on the bed, only saying “come blow me”. He lasted a long time, I deep throated him and massaged his balls. When he went, I was having trouble keeping up with swallowing. I lick off his dick and sit on my knees on the bed because he has a surprise for me. Read more »

Careful what you ask for… fucking my[21f] ex-bf’s good friend[35m] from prison.

I’m 21 and I broke up with my boyfriend of a year recently. I was feeling petty and called one of his good friends while I was drunk one night. They were friends while in prison, although my ex only did little over a year and this guy did 10 years. He’s much older than me and my ex, he’s 35. So it was the first time we ever really talked, first time we talked on the phone. He gave me his number when I first started dating my ex and told me if I ever needed anything I could call.

He showed up like an hour after I got off the phone with him haha I don’t remember what I even said on the phone but he didn’t waste time getting to me. I was home alone, he immediately showed up and sat on my bed and we talked for half an hour. He brought a blunt and a bottle of wine. Once both were finished he leaned in and kissed me. I pushed him away but he kept coming onto me. I started taking off my pants and I remember him being like “Oh my god, put your pants back on… you’re my man’s girl.” Read more »

Getting my Wife Pregnant

I have been thinking about writing this for a while as I enjoy this sub in my dry times and today I thought to myself why not I might as well pass it forward. This is the true story of trying for a third child. There is no anal sex or threesomes or other nonsense stuff as that is just not practical just plain old marriage sex so I hope this is good enough for you.

My wife is pretty vanilla when it comes to sex that is until we are trying for a baby in which case she heats up and she just seems desperate for sex and really horny. I am 40 and she is 37. She has a nice full figure and nice big tits with lovely large nipples. She has a nice full ass and is never shaved, the smallest bush she will have is a few inches of thin landing strip. She knows I like it bushy, there is nothing nicer than licking out a nice wet bushy gash. Lots of you young guys would call her a MILF and she is very very hot. Or sex life goes from rampant for a while to nothing for up to 6 months as being parents can be demanding. We have been together for just over 20 years. Read more »

My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times. Read more »

The Wait (part 2) [MF, Fsub, anal]

I am acutely aware of your cock stiff and warm pressed against me from behind while you woo me with your mouth and fingers. You inhale deeply at the nape of my neck and exhale a sigh that almost sounds like a long, purring “fuuuck…” but I can’t be sure because you’re moving away to aim your cock between my thighs. Now all I can feel of your body is the head of your cock poised at the entrance to my cunt. Face down in the bed and knees spread wide, I feel so exposed to you and the vulnerability rushes over me like a high. All I can do is lay there in wait for your next move… my cheeks growing hot with the agony of anticipation, fingernails dug into the sheets. Read more »

Rimjob and anal with a dirty girl [m/f]

Out at a bar, I started chatting up a cute woman, about 30 years old – brown hair, small chested but an ass to die for. She wore a close fitting top that didn’t hide either her small breasts or medium build, but I liked her confidence. She didn’t look sexy as much as she *exuded* sexy. Her skirt was short and loose and clingy enough that I could tell she had either a g-string or nothing.

One thing leads to another and she asks if I can give her a lift home, as she came with a friend. She had me park and invited me up to her apartment.

After getting up there she went into her room for a few minutes – I thought she was getting changed, but when she came out she had the same outfit on, heels and everything. She made us both rum and cokes, and we sat around, a sense of anticipation building, as we chatted to one another, flirting, talking politics and sex in vague but suggestive terms. Read more »

Mini-bukkake with girlfriend and friend [MFM]

Well the response to my last story (https://www.reddit.com/r/gonewildstories/comments/4ad4ap/first_threesome_with_girlfriend_and_friend_mfm/), the story of the first threesome that my girlfriend, friend and I had was pretty positive so I thought I might share another one with you.

Immediately after our highly successful first threesome I asked my girlfriend and friend whether we might like to make this a regular thing, to which they both replied ‘fuck yes’. We came to the arrangement that my friend could visit us whenever he liked and if my girlfriend was feeling up to it, she could relieve him. Needless to say, the combination of my friend having recently broken up with his own girlfriend and the chance of my hot brown girlfriend (who was truly a beauty: caramel-skinned and full-figured with ample breasts and a shapely butt) getting him off meant that he was always at my place looking for our companionship in one form or another.

Once or twice a week when he was over, my girlfriend would suddenly walk over to my friend, strip off her clothes and either push him back further into his chair, unzip his pants, pull his cock out and fellate him until he came in her mouth; or alternatively she would pull him forward and vigorously masturbate him until he ejaculated all over her big delicious brown nipples. Read more »

Had my [M] first jerk off buddy [M] today, things escalated quickly

TL;DR: found a jerk off buddy after a year of looking at this stuff, but the jo bud part lasted 10 minutes before it goes into make out, kissing, bj and 69. Did satisfied both my jo bud and bi-curious side in an hour, feel good now!

First off, its been almost a year that i stumbled onto r/jobuds subreddit and since then I was hooked to the stories and the community. I had a few jerk off sessions on kik in and off during the year.

I lurked on craigslist last week because I wanted to “get done with it once and for all” and actually do a real jo session with another. Found a guy that was about my age and shape, but the wording of the post sounded that he was more gay than straight bi-curious. I didnt mind because im a bit bi-curious so i wouldn’t have minded if during the jo session we would stroke each other. Read more »

My fifth time with my stepdad [mf]

My mom was out of town with her boss on business again so my step-dad being the cook that he is, brought me out for dinner. I sat next to him in a booth, touching his penis (over his pants) and whispering sexual things in his ear like “I’m so wet” and “Please violate my pussy”.

On the way to the car, he was squeezing and grabbing my ass calling me his pet. We made out for a bit by the car before he opened the door for me but he had one condition, I needed to strip down outside the car before he let me in. I also had to put my clothes in the back of his SUV. Since no one was around, I did this for him. He rubbed on my nipples and then told me to blow him. I was really nervous because I didn’t want a car coming by but did it anyway. After I swallowed, he let me in the car. Read more »

Achieve[m]ent Unlocked: I Sucked on a Penis

Since I was about 16, I had thought about giving oral sex to a man. At this point, I hadn’t even given oral sex to a woman, much less received it from anyone, but I had a desire to try it some day in the future. When my parents kissed me goodbye outside my dorm, the future was here.

Sucking a cock wasn’t the only thing I wanted. I had assembled somewhat of a sexual bucket list that I planned to attack in college. It mostly consisted of pretty standard fantasies: have a threesome, give a facial, have anal sex, have sex in public, etc. At this point, I was very inexperienced, so there were a lot of firsts to be had.

As soon as my parents drove away, I headed straight back to my dorm and got on my computer. This was about 8 years ago, long before I had heard about reddit, so my go to medium was Craigslist. I had browsed the personals in the areas around my home town before, but never had a chance to actually meet with anyone. I couldn’t exactly bring a stranger over to my parents’ house for some anonymous sex, and I don’t think my dad would have let me use his car to drive to a casual encounter. Read more »