Tag: Anal

“Blackmailing My Stepmom For Sex” [MF] [anal] [blackmail]

“Blackmailing My Stepmom For Sex”
“I’m in love with my stepmom. I don’t live with my Dad, but I stay with him and her two weeks a month. I swear, those two weeks are constant masturbation for me. She’s 18 years older than me, but, for some reason I always wanted to fuck her. I’ve known her all my life. She stays home and takes care of my half baby sister, while my Dad goes to work. I’m always sneaking around trying to catch her bending over or something. Taking a shower. Lying out in the sun with a bikini on. Anything.

Until the luckiest day of my life occurred. I left the house, but, ten minutes later, I came back to get something that I had forgotten, after I told my stepmom I was going to a friends house. I ran upstairs to my room. My baby sister was taking a nap. I walked by my stepmom’s room and the door was cracked open slightly. What I saw was a gift given to me. She was halfway sitting up in bed. She had a T-shirt on, and nothing else. She had her head back behind the headboard with her eyes shut, and her legs spread in the air, going to town on her pussy with a huge flesh colored dildo. I instantly got hard. I mean fucking instantly. I didn’t care. I pulled down my shorts and started to jerkoff right there outside her door. Read more »

My Sister Lizzy [MF] [MM] [FF] [Oral] [Anal] [BDSM]

PART 8

Looking down I could see Lizzy’s pussy wide open and a ton of cum poured out as it began to shrink.
“Holy Christ, that was so good, I don’t think I could do this on a regular basis but “Holy fuck” that was intense.”

As Lizzy rested, Tom managed to stand and stretch, his cock still hard as nails stood proud.
Dave and I were in awe of having watched Tom loose his virginity to the girl we loved.
What was even more amazing was that moments later Lizzy was ready again.
How did we know?
Lizzy spread her legs and asked if Dave and I would fuck her front and back.
That is a request that she didn’t have to ask twice.
Dave laid down on his back, while Lizzy mounted him. As she bent over I lubed up her ass and began the process of working my way past her little ring.
As Dave and I began to create a rhythm, Tom was closely watching the action, his face just inches from the point of our coupling. Read more »

“Creampie in the Wine Valley” [F/M] [Anal] [Coworker sex]

It’s not even noon yet, and I’ve already come twice and been well fucked every which way by my co-worker crush, Marc. To call him a co-worker though doesn’t paint the whole picture. He is a high-powered managing partner of the law firm I work for. I am the communications director based in Chicago, while he’s in New York. So even though we’ve been at the same firm for years, he’s only been on my radar in the past few months, thanks to my traveling more frequently to HQ.

The firm just had an all-hands retreat at a 5-star resort in Napa and after fantasizing HARD about Marc for several weeks now, not to mention abusing myself with my toy collection while thinking of him, it was revealed to us both by happenstance only yesterday that we’ve been mutually fantasizing about each other.

So here I am in the king-sized bed of his suite, which looks like it could be the Presidential suite. After sampling all my bits and making me come twice (so fuckin’ hot) and plundering all my openings with his fat cock, he gifted me a bucket of his warm cum deep in my rectum. We had dozed off, and I’m just now waking up to my favorite scenario. Spooning with a wonderful lover with his heavy cock resting between my inner thighs. Read more »

The Camgirl Part XXXII: Why Had He Been Mad? [FFM] [anal-kind of] [oral] [Bi] [Str8]

**XXXII: Liam**

Liam blinked in confusion as the door to Marie’s room closed before him. He should have known Blake would be up. Meeting her eyes had reminded Liam of the issues he’d been trying to work out concerning his friend. He hadn’t spoken to her since she’d confessed to him. Was that why she’d looked so sad? He would have to talk with her soon. For some reason, thinking about that—especially after her seeing him like this with Marie and Leah—

A nip at his lower lip brought Liam back out of his thoughts, and he grinned down at Marie, taking her by the back of the neck and bringing her lips up to his, sucking on her lower lip. He snaked a hand around Marie’s hips and squeezed her ass, eliciting a yelp from her, followed by a playful growl as she captured his lips again.

A moment later, they parted as Leah finished unbuttoning Liam’s shirt and pushed it off his shoulders. She pushed herself up against him and began kissing his neck, working her way up toward his jaw and then his mouth. Liam squeezed the tall blonde’s firm ass as he felt Marie’s fingers undoing his jeans, all the while shuffling him backward. Read more »

28 I[M] Da[T]ing a trans woman now

So this maybe a bit long, and I’m going to sound like a complete hypocrite, but here it goes. I’m a pretty big guy, 6’2 about 180 lbs, physically fit, not a bad looking guy, plus chicks dig my job. Anyways, I’ve been going to my hair stylist for about 4 yrs now. She has her own salon, about 2 months ago, I walk in like normal, usually packed so I sign in, I sit at wait. She smiles at me and we have our usual small talk. She introduces me to her niece, who’s now working with her and says I should try her as she has about 3 ppl in front of me.
I immediately notice how attractive her nice is so I quickly say what the hell. She tells her niece take care of my favorite firefighter, he is my favorite customer. I sit in her chair, and she begins to cut my hair, we have small talk and what not and I’m kinda really digging her. She finished it up and then asks if she could take a pic and post it to her Instagram account. I don’t mind and asks if she can tag me which I allow. So that happens, 3 or 4 days go by and I decided to get on Instagram while bored at the station. I see the notification and click. I notice get profile and follow, I look at her pics and like fuck shes so sexy. I notice a few pics of her with LGBTQ shit, me thinking she was with one of her friends. Anyways days go by and I kinda stalk her profile. I end up getting drunk out one night with my friends at the bar and notice she’s posting to her story. I decided to slide into her dms, but I kinda did it discreetly.
“Hey, (we’ll call her amanda) are u free next sat, I really like the cut and wanted to make an appointment.” Amanda-“Yeah, what time did you want to come in?” Me-“Anytime you’re free, I’m sure you have a lot of clients” A-“Just let me know I’ll make time for you so you’re not waiting” Me-” About 1 ish? I get out of work about 9 am and tend to sleep till about then” A-“Sat at 1 is great ?” Me- “I’ll even bring you lunch ???” so from there we continue to text throughout the night, as I got more buzzed, I got braver and just told her how beautiful i thought she was. We were sending pics to each other (nothing graphic) throughout the night so I got the vibe that she didnt mind. Anyways I’m not going to lie, I got home and was stroking my cock to her pics, while texting her. I took the plunge and asked her out the next day. She kinda bounced around the question a few times and again I asked her out. She tells me she’d love to, but I may not want to, I ask why and boom she hits me with it. I had no idea. I don’t respond to her for about 10 mins, which was weird cuz during the night it was a few seconds to a min or 2 between messages. I keep looking at her insta and decided to say fuck it. I told her I still love to take her out.
I pick her up and fuck she was looking so good. Jeans which showed off her nice fat ass, nice tits. We end up at buffalo wild wings to watch some college football and have some drinks. It really eased the nervousness for me, I loved how she caressed my leg, would snuggle into me I’d wrap my arms around her. It was great. We were sitting at the bar, when I notice my co worker walk in, I’m freaking out, but trying not to show it. He sees me and comes over, we talk and he introduces himself to her and she played it really cool. We pay and decide to catch the last game at a dive bar. As we walk out, i’m holding her hand and open her door. As shes getting into the car, I pull her to me and give her a kiss, she puts her hands on my face and kisses me back. My hands go from her waist to her fat ass, culling both cheeks. We break the kiss, I spank her and she gets in my truck.
We get to the bar and chill for a bit, both having more drinks and my hands all over her ass. She asks if I want to go to her place for a movie, of course. We get to her apt, I’m buzzed and really into her so the nerves are completely gone. She goes to her room and comes back to her living room in a tank top, no bra, and some super small booty shorts. She sits right next to me on the couch. We put on a movie, but are more so making out. She ends up unbuttoning my jeans and whipping out my 8 inch cock. She is stroking it as shes lowering my jeans to my ankles. She gives me a kiss as she’s stroking my cock, she asks if I want her to stop. Omg fuck no baby. As I sit on the couch she lays across the couch with her head in my lap as she starts to suck my dick. Omg it was definitely the best fucking blowjob I’ve ever had. I play with her hair, put the TV on mute because I wanted to hear her slurping on it and wanted the continue seeing her suck my dick with the light from the TV. I have one hand on her head guiding it, my other hand on her back moving to her ass. I caress her ass, slide my hand in her shorts. Her ass was so soft, I tugged down her shorts with her panties, as she continues to suck on my dick. I caress her ass, sitting there enjoying the service shes giving me. My balls tighten and I can’t hold it any longer “baby, imma cum” i hold it for a few more seconds as she doesn’t stop. I shoot my thick load down her throat, she then cleans me up. I sit there a bit spent, she sits up and I notice her large clit, she has a small dick, which actually kind of works out, cuz that’s obviously not what I want. We go to her bed room and cuddle a bit, we talk about her head game and just have good convo for about 30 mins. I pull her to me and kiss her, she sucks my cock again and get me rock hard. I ask if she has condoms, she gave me one as she put it on me. She asks if I’ve ever had anal sex, I haven’t, she tells me to slide in slow and let her do the work.
We spoon as she reaches around and grabs my dick, she slides it in, I grab her hips and we rock back and forth a bit. I’m finally fully in her as I kiss her neck and back. We start to slowly fuck, she sounds so sexy. We end up in doggie, which drove me fucking wild, hands on her ass going to town. Then she rides me that’s where I lose it, she rides me till i cum. I was using a condom obviously. I’m going to sound like a hypocrite, I’ve never liked transgender people, i don’t mind the gay community, but i just feel that the transgender community tries to get everything catered to them. I’ve been consistently seeing her for about 2 months now, I’ve brought her around my friends, dates, people. Nobody knows, which is good, she seems to be okay with it. The sex is so fucking amazing, best sex ive ever had. I know I’ll probably get some shit talked to me, but who cares. I have pics of her. Kick me if you have any questions chriswhite1996

“A Series of Confessions: Lot 1” [F] [MMMF] [MF] [anal]

“A Series of Confessions” Lot 1
I’m just trying something different, to see if you like it or not. When I had my Instagram page, before it got taken down, I would ask people to direct message me their anal confessions. I actually got a lot. People trusted me. I wrote some of my own, too, and posted them. I just never would tell if they were mine or someone else’s. So, since it’s Saturday, I wanted to share three short confessions from my deleted page. If you let me know if you like them, I will post more, from time to time. Thanks readers. ?

ANONYMOUS CONFESSION #1 Read more »

[MT] My girlfriend became my boyfriend, who became my biggest fetish

Three years ago I started dating my best (for all I knew at the time) female friend. We are a good match, so the relationship was pretty good. Our only problem was our sex life.

At the time I knew my partner had some deep trauma regarding sex, so we took our time. A year into the relationship we had a talk about our non existant sex life, which ended with my partner coming out as a trans man. After the initial shock, we continued stronger than before. My boyfriend is in a pretty shitty medical condition, so transitioning will probably never be an option. His family is religious, hence he is closeted and presenting himself as female for the time being.

So now I have a biologically female boyfriend, who to the unsuspecting eye is a hot pawg. It’s kind of an awkward situation sometimes, but I do my best to make him feel manly. Turns out we could never have penis-in-vagina sex because he hates his vagina. The next logical conclusion was “Dude if we are gay, shouldn’t we just do anal?”. Which was a great idea. Half a dozen of tries and two buttplugs later we were fluent in anal, and turns out anal is the best. It’s tighter, ribbed, and I can go way deeper. Doing it made him feel manly, which made him horny, and him being horny made me even more horny. Read more »

My Girlfriend got RAPED–by a ROCKSTAR!

[When I was 18, my girlfriend went to a rock concert without me. In the front row. (I had to work that night.) Below is an account of what may or may not have happened after the show. To avoid litigation for libel and slander, Billy’s last name has been scrubbed from the this written version, but it was definitely one of the 5 top touring rock musicians named Billy, and to this day, if you tune to any rock station for any length of time, you are likely to hear one of his songs…]

“Big After-party, Eh?” Said Melinda, glancing around the hotel room with a skeptical eye. It was a small hotel room, definitely not what would be called a hotel suite. And not even a particularly nice hotel. Not fit for Rock Royalty, or even a Knight’s stay, for that matter. Yet the man standing before her was most certainly a millionaire, multiple times over. And so it quickly dawned on her that this place was where he took his groupies, before going back to the real hotel, to be with his wife, or girlfriend, or whatever. But Melinda wasn’t a groupie! Was she? Read more »

Becoming his slut Pt. 2 [MF] [Anal] [ Exhibitionist]

Ronaldo had not finished with Melissa just yet. Though he had just covered her breasts in ropes of cum, his erection still raged on. He was filled with the desire to have her in every way possible.

Grabbing a fist full of her hair, he pulled her so that she was on all fours and walked her over to the window.

It was dark now, but the glow of the streelights and lights from neighbouring houses lit up her body in all the right places. He could see the lust still burning in her eyes. Her expression was one of insatiety.

He loved her like this. Hungry. Wanton. His. There was no time to waste. Quickly, he positioned himself behind Melissa and plunged deep into her . He knew the neighbours would hear her screams but tonight they would also get a show.

That knowledge pushed him into high gear. With one hand in her hair and the other pressed firmly on her lower back, he drilled her mercilessly. It was not long before her breathing quickened and his cock was dripping with her juices. Read more »

“The Much Needed Family Vacation” [long] [story surprise] [anal]

Story taken from a man’s POV. ?
“The Much Needed Family Vacation”
”Her ass was so young and tight. I could tell by how much I have been paying attention to her everyday for at least three years. She was so sexy, but, oh, that ass. I don’t even think she knew it. I mean I know she knew she had a nice body, but not on this level, to me. I’m pretty sure she didn’t know about me, thinking of her, in this way. Every guy that saw her probably whipped their dick out in their bathroom only to jerkoff imagining that they were sticking their dick in that perfect ass, and filling it up with their cum. I wonder if her boyfriend, and ex boyfriends got to taste and fuck that ass. I actually wonder if she likes it back there. You’d think she does, by the way she presents it. The skimpy tight shorts, skirts and pants.

I was actually able to take a picture of her pussy staring back at me from under a table. I was shocked to see that she wasn’t wearing any panties. I drowned that pic with the amount of cum I expelled jacking off to it. Regardless, if she was really into anal sex, or not, in my fantasy, she was. Read more »