Tag: Anal

How I lost a bet with my bf and got my ass fucked [MF]

So my bf (20) and I (19) are currently staying in a aibnb. We are staying there for 3 nights. The first evening, we made a bet. If I won, I would get to pick our vacation for the summer. If he won, he could fuck my ass anytime he wanted until sunrise. The bet was pretty unfair because he was sure he would be the winner. We had a bottle of vodka : the first one who couldn’t continue to drink would lose. Well, I won.

We do this sort of bets pretty often. Usually I win and we go to a restaurant, sometimes I lose and I get fucked really hard. Tonight we made another bet. He would get my ass. I would get ice cream (paid by him). I had 10 minutes. If I succeeded in making him fuck me, I won. He set up a timer and I went down on him just a little. After that, I asked him to get on top of me. His dick was on my pussy, just at the “entrance”. I started playing with it, mastubating with the tip and giving him a handjob. I talked about breeding and did everything he likes but it didn’t work. I lost the bet. Read more »

Cucking her ex by accident and training her body to love deep penetration [MF]

22 cm = 8.5 inches

I matched with this hot girl on Tinder. She had a pretty serious profile with some nice pictures which looked promising, though she had one picture showing she had a dark side to her as well. Still, I though it was worth a shot.

After talking a bit, she shared was living with her ex-husband. They had broken up some time ago, but due to economic reasons she chose to stay there until she found someone else. Asking if they were still sleeping toghether, she admitted they were having a fwb arrangement going, which admittedly felt more than just a bit wierd as I heard her ex in the background sometimes while we were talking.

She looked serious from the dating profile, but the more I got to know her the more I realized she was a dirty, dirty girl with a lot of red flags. She loved sex and had been with a lot of men over the years. During our convos, she also admitted making porn videos, including some with her ex she was living with. She linked me to her videos, which were anything but softcore. Read more »

The day I [F] lost my anal virginity

I was lying in bed with my boyfriend, feeling the heat of the summer sun beating down on my skin. We had been together for a few years and had always been open to trying new things in the bedroom, but today was the day I had been thinking about for a while.

I mustered up the courage to bring up the topic of anal sex. My boyfriend was a little surprised at first, but he was open to it and we talked about it for a while. He made sure to reassure me that he would be gentle and take it slow, and that he would make sure I was completely comfortable and relaxed before we started.

The day of, I was a bundle of nerves. I had never done this before and I was scared of the unknown. But my boyfriend was patient and understanding, and he made sure to go slowly and use plenty of lubricant.

I lay on my stomach, feeling the soft sheets beneath me and the warmth of my boyfriend’s body behind me. He asked me if I was ready and, with a deep breath, I nodded my head. Read more »

[MF] my first experience with an older woman. M23 and F55

Hi, this quite a long story but I wanted to share this story from my life. I hope it will give you all an appreciation for older women and how amazing they can be.

When I was 23 I was doing shift work at customer service centre, day shifts and night shifts.

I worked with team of 5, me and 4 other women. All nice people but I wasn’t planning to date any of them. One was Diana (not her real name). She was 55, about 5’3 with short fading blonde hair, blue eyes and slightly chubby but nice skin and she wore nice makeup. You could also tell she had an impressive set of breasts under her clothes, but you try not to look. She had been working there for years and I had only been there 6 months.

We didn’t speak much as we were mostly on the phone. She lived near to the building and walked to work but I had drive in. I was still living with my parents at the time, saving for my own place. One day after a night shift and it was awful weather outside, wind and rain I offered her a lift home which she accepted. I dropped her off, she thanked me and I continued home and didn’t think anything of it. Read more »

Collared in public – Anal, Ass play [MF]

Yesterday was wild.

We woke up from an amazing sleep. We cuddles and asked each other about our sleeps and dreams. Lily dreamed of some nonsense and I of course dreamed of some lewd acts we committed together.

We Lily wanted to go to the mall before the Christmas crowd. I came up with an idea. I asked Lily to pick the toy(s) she’d like to wear to the mall. She thought about her anal plug, but didn’t want to be plugged for too long, and it isn’t comfortable walking for long periods of time. She was worried that people could see her nipple clamps, if she tried on clothes. She quickly wrote off wearing her handcuffs, ballgag, and blindfold. With a devilish smile I suggested her collar.

I’ve been very turned on with the thought of collaring her. I would love for her to wear a permanent collar that only I have the key for. I was looking at fancy necklaces and titanium ring collars. Since Lily isn’t really into that I respect her wishes and haven’t bought any.

We do have a velcro collar that came with her nipple clamps. (there’s a story of her wearing it in my profile) Read more »

New Gym Equipment [MF]

New Gym Equipment [MF]

*Ping* [Meet me at my truck before you head in]

I am pulling into the gym parking lot when my phone went off with that message. We had been “continuing our exercise” in his truck after our workouts for the last 3 weeks. No matter how light my workout was in the gym I knew I could always get a harder post work-out pump in with him. I saw his truck parked in the back of the parking lot and pulled up beside him. He motioned me to the passenger side, and I walked around and jumped in.

“Hey baby, Good morning” He was looking at me with his signature smile- with the corner of his mouth up. The one where I knew there was something mischievous behind his eyes.

I leaned in to give him a kiss. I couldn’t help myself by to slide onto his lap, my body automatically responding to being in his proximity. My pelvis started to grind onto him, and I could feel his erection growing. I broke away from our kiss and whispered in his ear “Lets skip the gym this morning.” Read more »

A Bully Caged, Pt. 3 [M/M] [Bi] [Chastity] [Public]

[Part 1](https://www.reddit.com/r/Erotica/comments/zce8mk/a_bully_caged_part_1_mm_bi_chastity_implied)

[Part 2](https://www.reddit.com/r/Erotica/comments/zh3k7t/a_bully_caged_part_2_mm_bi_femdom_chastity_bdsm)

Thanks for the great feedback and reception so far! This installment is longer, but I wanted to get to the payoff at the end. Hope you enjoy.

xxxxxxxxxxxxxxxxxxxxx

Wes stayed in our guest bedroom last night, freshly showered. He thanked Ms. Simmons for dinner, he thanked me for my cum, and he went to bed almost immediately without another word. I was confused, and it was another hard night of sleep. My mind moved in waves, and every time one would subside, another would rise, bringing new anxieties, frustrations, and questions with it. What was going through Wes’ mind? Did I go too far? Would this last? Was it already over? I have no clue when exhaustion won, but I’m thankful it did.

When I wake up, I’m tired. I reach over to my nightstand to turn off my phone’s alarm, and my hand finds an unfamiliar chain. It rattles when I pick it up. I turn off the alarm and turn on my flashlight, casting a big, fat shadow of a chain against my bedroom door. My eyes adjust, and I see it’s a black metal. On one end, there’s a small open padlock with a simple “D” engraved on it, and the other end hangs loose from my hand. It’s not a long piece, and suddenly, I realize that it’s the collar Ms. Simmons had mentioned last night for Wes. This is supposed to be around his neck, and I am supposed to put it there.  Read more »

Having a lovely time in her ass (highschool sweet hearts – 23) [MF]

Rebecca and I started seeing each other in the summer of 11th grade. I had been with two other partners, she hadn’t been with anyone before. We spent the summer hanging out nearly every day. Making out, then making out with her top off, eventually her going down on me, me going down on her, she just wasn’t ready for sex.

When we were starting back up 12th grade, we were hanging out at her parents place one night after they had all gone to bed. We were making out, her in this sexy dress she had, no underwear on… I picked her up and was grinding my cock against her pussy. We were both so wet and aroused, I had been playing with her ass a bit before and my cock slid in, she moaned loudly, and sunk herself deeper on my cock, before realizing what was happening. She sat there for a moment before sliding off me.

We kept making out and she said she still wasn’t ready. Fast forward a year, on her 18th birthday we had sex, and soon after had gotten right into anal. Read more »

I’m A Gay Simp For Hot Straight Cocky Alpha Males. I Like Roleplay Too

29 Gay M Detroit Based. Simp for tall, muscular, cocky straight guys. Love hearing their hook up stories, crazy shit they’ve done. Telling them how I love their bodies and wishing I could play with them. Love getting rebuffed and told there’s no way I’d have a chance. I prefer 22-40 yo studs. If you wanna chat, dm me.

have lots of roles I’d like to try:

You: Str8, Cocky, Arrogant, Tough Alpha Male. 6’5 tall, muscular (I have pics of guys you can play as), packing a beautiful 8×6.5 dick. You know you’re sexy and can get any chick you want. You’re all about your pleasure and love to fuck rough.

Me: Gay Beta. Shy, maybe a little odd. 5’5, skinny, black hair. Brown eyes.

I like my roleplay partners to play hard to get-be annoyed by my character at first or weirded out. I also like things to play by ear. Read more »

EST: The Case of the Moana Lisa Chapter: 8 (FF MF Anal Rough Forceful)

feeling the soft spongy texture at the end of my fingers. “One more” I thought as they slipped back down towards her lips. Back down towards the exit back into the world of light! With my next thrust, the impact not perfect butt enough to get that tightening feeling of an orgasm.
My hips trembled as they continued to jack my cock deep in Mila’s throat. As she sucked on my dick I could feel her wetness. I could see her creaminess as the last impact had sent goosebumps up her pelvis. Now it was my turn. As my hand dropped! Lifting it just as quick. Torturing her g-spot with every move. Torturing my own piece of mind with every thrust into the beautiful mouth of hers.
“I want to hear you moan” my whispers did not go unnoticed. From the shiver to the roll of stomach muscles. From the extra practical squirting to the tightening of that fucking hole I knew that something right was happening. Read more »