My [tf] first time giving a blowjob

A bit of background first on me! I’m 23tf and started transitioning just after Covid started and so spent a year or so locked up by myself. When things began to get more relaxed I wanted to try putting myself out there again and got tinder. That’s where the story starts…

I was already horny while I scrolled through tinder, swiping on anyone that didn’t seem too creepy. One match that caught my eye was a slightly older man (38) and we hit it off immediately.

What started as cute and innocent flirting quickly turned into him asking me to send pictures and then him sending back his own. When I saw his cock I knew I needed it and invited him over on a night I knew I’d have the house to myself. He said he’d have time to come over on the way back from work but he couldn’t stay long.

I was so nervous and spent ages doing my makeup and getting ready before he arrived. I wasn’t sure what to expect or what was quite going to happen but there was no way I was going to back out now. The doorbell rang and there he was still in a suit from work. He grabbed me and kissed me, pushing me up against the wall.

It all started when I 45[F] let a stranger 22[M] finger me until orgasm in a bar in front of my husband 47[M]…

My husband has a kink: he has always loved the idea of another man flirting with me and having his way with me. I happen to have no issues whatsoever with this arrangement, and I’ve fucked a few guys during our marriage, all with his encouragement. A month and a half ago on Friday night, we went to a bar pretending we didn’t know each other, something we do every now and then. Sometimes we do the classic “strangers meeting in a bar for the first time” roleplay and have amazing sex with each other afterwards, but occasionally it goes a different way…

I sat in a corner booth, he sat two tables away. The bar was relatively busy but he had a good view of me. Before long, a handsome young guy, Brad, slid into the booth next to me and started making conversation. Tall (I’d guess 6’2), dark and handsome, with a fresh haircut, and clean shaven.

We played guess my age; he guessed 35, I’m actually 45. I guessed 25, he’s actually 22. I mentioned that my children (21 year old son and 18 year old daughter) are younger than him, which he seemed to find amusing. The conversation flowed as naturally as the drinks did.

6 Months of the most Erotic….Part 2 (NSFW, INCEST, Wife-sharing)

After a few months of having “T”, our 19-year old friend and 3rd, sleeping in our bed a few nights per week and fucking my wife all the time, I met Juliette while bartending a party in South Beach. The party was a real estate showing at a 5-star hotel and condo property on the beach, and my bar was by the pool closest to the beach and walkway.
Juliette had just filled out an application at the hotel and was walking by to leave when we caught each other’s eyes and held a gaze until she walked up to me.
Wow was she my type! She was 24, 5’6″, 105 lbs skinny and firm with round B cups. She had curly auburn hair and green eyes that looked like they had seen through a lot of pain and LSD. But they still smiled at me.
She had skin tight jeans that ended at her calf, hemp shell toe Adidas, a belly ring, and flowered button up that tied under her tits and exposed her slim waist. She was a total smoke-show. Her face was beautiful but had an amazing imperfection I found so sexy.
As we spoke with a fence between us, she pulled out a blunt and lit it. We shared it over the fence, exchanged numbers, and she departed after a kiss in which she lightly bit my bottom lip as she pulled away. After walking 100 feet away, knowing I was still staring, she turned around and blew me a kiss.
We made a plan for Saturday night after my work. My shift finished before wife, and I left at 11. I got 10 pills of ecstacy from T, as Juliette loved it like I did. T would close with wife, drive her home, take a shower with her, then fuck her to sleep. Turns out. That particular night, T’s friend ended up crashing at our place, and wife got fucked by both of them all night.
At 11:30 I arrived at Juliette’s apartment. I needed a shower, so we both popped 2 pills and took a shower. It was a 1 bedroom apartment, and I saw obvious signs of a male occupant, as the bathroom was en-suite, not in the main apartment area.
“I live here with my younger brother, Jake. Our dad was an abusive asshole and 5 years ago, I took Jake, who was 16 then, and we left Coco Beach for here. He’s at work now at the bar. He will be home later. You’ll meet him. He’s really sweet, a nice kid. Our dad used to beat the shit out of him, but he’s ok now.”. She was saying all of this while sitting on my ass naked, massaging cocoa butter into my back. We had taken a shower for the first 10 minutes of our first date and had an amazing familiarity that made us incredibly comfortable immediately. We both knew why we were there, I want it, you want it. We found each other flawless in our obvious flaws. She was a perfect female specimen for me, and possessed a compatible crazy to my own.
Not every brand of crazy can coexist in a relationship. But ours were so drawn to each other. They shared an obvious disregard for the niceties of civil society in which we actively participated, for the occasional tryst into unbridled eroticism that was nobody else’s business…. Not like animals, or shitting on each other. And I’m not wild about piss, either. Nothing violent or distasteful like that. But an openness to each other that stayed within our bond, total comfort without judgement.
So now it’s an hour into our first date, the entirety of which we have spent naked. The bedroom is lit with some covered lamps and screen saver over her playlist on stereo speakers. We’ve been massaging and kissing, making eye contact as our pupils grew. We layered compliments to each other while kissing and I massaged her face and tits. Back and forth, falling in love minute by minute. Kissing her and at one point passing a joint down to her.
Now she was sitting on my waist naked. Unconsciously she was humping back and forth. Rubbing on my chest and abs, she was getting hornier.
“Mmmm. Your body is so fucking hard,” she said. “And your big, hard cock….mmmmm…where’s your wife tonight? I want to call and thank her for lending me your beautiful body!”
I looked at the clock but my eyes were getting fuzzy from the pills. Almost 1am. “Right now she’s cleaning down the bar and probably just snuck off to get fucked in the storage room by her 19year old boyfriend,” I answered casually.
“Oh wow. That’s so fucking hot ” Juliette said. She slid down to start sucking my dick. “Do you like to watch her get fucked by her boyfriend?”
“Fuck yeah. It’s so hot.”. I replied. “And tonight he has a friend from home staying with him. Wife texted that he’s hot and she will probably fuck both of them tonight.”
“Do you want to watch me get fucked?”
“I don’t know… Do you love me? It’s only hot if you love me.”. She slid up my body to look in my eyes and kiss me.
“Yes. I love you. I love you so much.”
“I love you, too, Juliette. I wish I could marry you tonight and I would love to watch you get fucked.”
“Mmmm good. Anything for you baby.” She went back to sucking my dick and we heard a key in the lock. “It’s Jacob. He knows you’re here,” and went back to sucking. He put his stuff down and kept the lights off, but it was still not pitch black. And I knew that he could see his sister’s ass and shaved pussy facing the door way as she blew me on all fours. If she doesn’t care I sure don’t. He walked into the bedroom.
“Hey baby. This is Alex. Alex this is Jacob,” she stopped long enough to say. He gave me a fist bump and exchanged pleasant ‘whats up’s’ with me.
“I’m gonna shower,” he announced.
“There’s 2 pills right there,” she said. “Take them then come hang out after!”.
“I will. Thanks!”. He shut the bathroom door to turn on the light and not bother us. The shower started and we heard him get in.
“You’re not going to say anything about me doing this naked in front of my brother?” She asked inquisitively.
“I don’t care. It’s hot as fuck.”
“Right answer!” She said playfully with a little clap, then went back to sucking my dick. “When we were younger, Jacob would stand up to our father sometimes to protect me, and get the shit beat out of him. My father used to make me give him blowjobs, and when Jacob would protect me and get beaten up, we would run and hide in the basement and lock the door. I started giving him blowjobs to make him feel better.”
“Always works for me,” I said. “So hot.”
“Then when we ran away and lived alone, we always shared a bed and started fucking our first night alone. For a long time, the only people who ever came inside me were my father and my brother. Do you want to see my brother cum inside me?”
“Yes ”
“Good. I love when he cums in my pussy. Do you want to cum inside me?”
“No. I NEED to cum inside you or I’ll die.”. She got on top and started to ride me and came hard. After a few minutes Jacob came out in a towel brushing his teeth. He spit, rinsed, and walked over to the bed. Juliette leaned over and kissed him. They started making out and she got off me and laid down. Jacob dropped his towel and climbed on top of her. He put his dick inside her as they kissed. Without a word he begins to fuck his sister. He has a big dick, too. She’s yelling and cumming, and finally he groans and slams her hard while he unloads inside her. He got off after some kissing and I replaced him.
Feeling a brothers cum inside his sister’s pussy was crazy. I came so fast. We talked so dirty and I came in her pussy for the first time.
We hung out and smoked weed, cigarettes, drank Gatorade, showered, and fucked. We masturbated ourselves and each other. Juliette wanted to watch us jerk off and then cum inside her.
I watched her make tender love to her brother, starting with a blowjob while telling me,
“Our mother died when Jacob was 7 and I was 11.” Suck suck suck ..”when I was 12 our dad told me I had to replace my mother and take care of them.” Suck suck suck. “One night after bedtime he called me into his bedroom. He shut the door behind me and told me to sit on the edge of the bed.” Suck suck suck…”he stood in front of me and told me to open my mouth.” Suck suck suck ..”I did, and he took out his huge cock and put it in my mouth. He held my head and fucked my mouth until he came down my throat.”. Then she climbed onto her brothers cock and leaned down to kiss him.
“He did that every night and made me sleep in his bed naked. Soon he started fucking me at night. He told me he was going to put a baby in me, and came inside me every night multiple times. I didn’t want to, but he was really big and gave me huge orgasms. I got pregnant and had miscarriages so many times…. Oh my God yes!” As she rode her brother. “Now Jacob is going to put a baby in me, aren’t you, brother?”
“Who’s pussy is this?” He asked.
“It’s your pussy! It’s my brother’s pussy! Cum in me baby!”
“You want it? Huh?”
“Yesssss oh my god do it!” She yelled. He gripped her hips and held her down as he thrust up into her, shooting his seed deep into his sister. Then I got behind her and added my own cum inside her.
Later in the day we 3 were in bed.
“Jacob is bi and wants you to fuck him, so I’ll leave you two alone for a while,” she told me before she left the room and shut the door. Jacob immediately went for my dick, sucking it aggressively. He was really good at it. Then he just said. “fuck me.”
I got behind him, and my dick slid into his ass with little resistance. He had done this before. It felt amazing though. I held his hips and fucked him until I came in his ass. When I finished, I stayed inside him as we rolled to our sides and I jerked him off and felt his huge cock pulse in my hand as he came.
It was an amazing night. I can’t believe how much I liked it, but I would go over to fuck Jacob a few times a week and cum inside him and let him cum in my mouth while telling me about fucking his sister or being young and hearing his 14 year old sister getting fucked every day.
And I obviously continued my individual relationship with Juliette, her becoming my girlfriend.

Going to the Kellers’ (Part 3) [MFFF] [Just Friends] [Vacation]

As we were exiting the master bedroom, Lexi stopped me.

“You’re going to get too hot in those,” she said, motioning to my sweats.

“I’m only wearing boxers underneath,” I replied.

“May is only wearing yoga shorts, I’m only wearing panties, and Bri is only wearing a thong,” she insisted. “You’ll get way too hot in them. Trust me.”

With that I left my sweats in my bag and continued to the living room in my boxers and a t shirt. Lexi was right. It was still very warm from the hot summer day.

Missed Parts 1 & 2? Start by reading Part 1 here: https://www.reddit.com/r/eroticliterature/comments/u0q3ud/going_to_the_kellers_part_1_mfff_just_friends/?utm_source=share&utm_medium=web2x&context=3

We all hurried excitedly to the living room. We grabbed blankets and Lexi grabbed us some snacks from the pantry. Thankfully she had licorice, which is my favorite movie snack.

We hadn’t decided on a movie yet so Lexi pulled up her Hulu account on the TV so we could decide on something together. We all got situated on the couch in the meantime. It was a pretty small couch considering the size of the lake house. We all had enough room, though, to kick back and lounge in a reclined position side-by-side. May was positioned to my right. Bri was to my left. Lexi was standing up near the kitchen, multitasking between flipping through Hulu and grabbing us drinks and snacks.

The time some friends and I [F] [Group] got drunk at a birthday party and an innocent game of truth or dare (but mostly just dare) devolved into absolute sexual degeneracy (Long Post!)

**(I have hundreds experiences I can tell you guys on here, and this is just one of them! I loved telling my last story yesterday and can’t wait to tell more of them! I hope you all enjoy.)**

**Just curious if people prefer long stories like this to be written on a single post or should I break them up into parts and make 2 or 3 different posts? Let me know in the comments for the future. Thanks!**

**I’m sorry if the story kind of drags on for too long, I like to give as much detail as my memory will allow. I write these for my own entertainment mostly, because reliving these memories turns me on haha. But yeah, I know it’s a long post and I salute anyone who manages to read the whole thing. Apologies in advance for any spelling errors. I wrote this on mobile without autocorrect.**

**I can do a Q/A in the comments so if you have any questioms feel free to ask!**
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Where Were We?

It’s a blazing hot summer day in July. In the hills of Los Angeles is a house built into the side of the hills that overlooks the city.

From an aerial view we see two women, sun bathing. The women lay on patio loungers only feet from the pool’s edge.

The woman on the right is Payton, a 19 year old siren, her black hair tied into a ponytail matches the color of her sunglasses. Her skin is fair but not pale. Her breasts are perky and her butt is firm yet jiggles when she walks. Payton is wearing a pink bikini two sizes too small.

Next to her is Claire, The 39 year old mother of Payton’s boyfriend Kyle. Claire is stunning for her age. Bleached bimbo blonde hair. Her skin, tan from over the years. Clair is wearing a one piece leopard print swimsuit.

Sitting at the poolside bar drinking a dirty martini is Derek, a typical frat boy. Blonde hair, black Ray-Ban’s, Puka shell necklace and long board shorts. Derek has a California tan and a lean, chiseled body.

My Best Friends Sister

The party is popping, the music is bumping and the drinks are flowing. I have a pretty good buzz going on, this Friday night. My best friend Mario was throwing a rager at his house, celebrating the beginning of Spring break. His parents had left for the weekend. So, of course Mario spared no expense. He hired a DJ and two bartenders who are mixing killer drinks.

Mario’s house was packed full of drunk, 20 something horny college aged kids, me being one of them. There were plenty of really hot girls at the party but only one girl had my attention. Mario’s twin sister Vella.

Vella is on the short side, maybe 5’3 or 5’4. Long, wavy jet black hair with blonde tips. She has stunning light brown almond shaped eyes and always wears heavy black mascara, the total pornstar look.

Vella has a toned hourglass figure with a cute round, juicy butt and a pair of plump D sized breasts. Tonight she was wearing a white tank top with a black bra underneath and black yoga pants.

She put a spell on me, Then I lost her (Naughty Photoshoot) [MF]

She put a spell on me, Then I lost her.  I had an amazing day of fun…I was talking to a lady FWB and another new lady friend. They both agreed to meet. This would have been my 1st 3-some with 2 ladies which is on my bucket list. It almost happened but one had to cancel.

So, I met a friend at the hottubs for lunch. We kissed and made out. Played with her pussy making her and cum hard a few times. I would lick her pussy then suck her clit into my mouth driving her crazy and cumming hard. She sucked on my cock which felt amazing. I pounded her pussy deep and hard. Several times her pussy would push my cock out as she squirted! She came about a dozen times. Her bush is all natural which causes my cock to get a bit rare with all the pounding, but It was fucking hot! 

The night before I was chatting with another lady. She wanted a sexy boudoir photoshoot. She was very fun and sexual. We started sexting and then sharing naughty pics. We both got off that night on cyber.

Me (18M) becoming my best friend’s (20M) crossdressing sissy girlfriend. CH 01 – First Encounter

Jackson and I grew up just down the road from each other. I always called him Jax for short. Even though he was 2 years older than me, he never acted too cool to hang out with me and during our teenage years we spent a lot of time together.

As we got older I began to notice him a little more. Maybe I looked a little too long when he took his shirt off at the pool and caught a look at his butt when we had to change clothes or something. I never thought I was gay, but Jax just seemed stronger and more masculine then me. I never developed the strong chin and jawline he did and I could never grow any facial hair. I was just thinner and smaller than him and never gained any muscle. I was just “softer.”

I remember how it started… I was going through a goth emo phase. I grew my hair out and let it fall over one side of my face. My dad hated it, but my mom encouraged it. I even wore a little eyeliner from time to time. I guess I was just trying to find myself.

Getting Railed – Fucking on a Train (29f) [FM]

As I sit currently bored out of my mind on a lengthy and tedious train journey I can’t help but cast my mind back to a happier time: A rare instance in which I could get railed on rails.

Grant and I have been infrequent colleagues for a number years. Which is to say that we’re both a pair of poor-done-to freelancers who occasionally find ourselves working on the same project. He’s got the build and stature of a rugby player; broad and excitedly rugged, and a sharp and witty mind which I envy as much as I adore. However seemingly as if to compensate for being so generous with these blessings, fate deigned Grant with the most plain and forgettable face you could care to imagine.

Actually, I lie. You couldn’t possibly imagine it. It’s simply too nondescript.

The best I can manage in terms of description is if you were told to put together a police identikit image, but altered nothing beyond simply including that he possesses ‘Eyes, nose and face.’

And for anyone wondering – I’m not being cruel or speaking out of turn here. I’ve said all this to his face. To his plain, uninteresting face.