A boy and his toy [m] [anal] [mast]

It feels so good.

The cool, bulbous tip gently spreads my tight hole. A moan slides out, involuntary but deep and loud.

Riding this glass dildo is my favorite thing, the only orgasm to leave me quaking and twitching since the first time I had sex without a condom, unloading my full heavy balls in thick endless spurts into my girlfriend’s white-hot hairy pussy and watching it form streams of sexual magma that flowed down between her lips and my thick cock under her wide blonde landing strip.

So I suppose you could say I like anal, which is a recent discovery.

I bought the plug first and quickly got bored, so I replaced it with a dildo with a slightly narrower tip and 8” of gently curved length. Cool blue spirals, slightly raised, start below the much wider tip and run down the length of the shaft over the clear center.

I rode her for the first time and shook with joy but couldn’t cum.

The second time I rode her for 25 minutes before I ejaculated. The orgasm was insane, almost not tied to the act of shooting cum, deep within me and in my cock and in my balls and in my twitching bumhole.

Story of J – Chapter 4

The sun had set and the sky was a dark shade of purple. Off to the east, the sky crackled bright from a flash of lightning of an early evening thunderstorm as Jenni glided through the parking lot to her car.

Her desires took control of her reasoning once again. She peeled open the car door, flopped down, pushing back in the seat. In one continuous motion Jenni stripped off her shoes and shorts, popped the pills over her tongue to the back of the throat, took a couple of big swigs of beer, cranked the ignition and the stereo, pushed down on the window levers, lit the joint, and pulled the car out of the lot and headed south.

UPDATE [MF] Last night I met a couple at a bar

My hubby’s side of the story, I’ll try to get the details the best I can ;)

So when I was playing with them at the bar, he was lounging by the pool having a few beers. After I sent him his surprise was on the way text he said he figured I was up to something and came inside to wait for the door. He said his cock was already getting hard in anticipation, and after the doorbell rang and he answered it, his cock was rock hard as soon as he saw her. (For the record, she was VERY curvy with enormous tits spilling out of her shirt). She asked if he was going to invite her inside, and he led her to the kitchen to make them a drink.

As he was getting their drinks ready she asked if they could go out to the pool, and took her clothes off down to her bra and panties in the kitchen. He said she walked up to grab her drink from him and pressed her body up to him presumably to feel his erection, and sunk down to her knees to press her breasts against his cock. He thought she was about to start a blow job, but she stood up, grabbed his hand and led him outside.

[M]y first time bottoming for another [M]an

Few years ago I was working as a tech for a server and data center parts manufacturer. I routinely made repair calls to some of our larger clients out of the immediate area, and would be put up in a hotel room with another associate until said repairs are done.

On this particular occasion I was fresh out of a hetero relationship, and wanted to get over it the best way I knew how.
After day one’s work is over it’s time to hit the bars. Tried a couple places but had no luck finding a girl so far. In my inebriated state of mind and needing to find some action before last call, I decide it’s a great night to explore my bi fantasies some more. I had given oral to a couple guys in the past, quick encounters whom I met online, but nothing more.
I turn to Google and find there’s a gay bear bar in walking distance. This is too perfect as that describes me, as well as the type of guy I am into. I down the rest of my drink and head out.

How I ejaculated 5 times in less than 4 minutes with the assist from my beautiful wife. (We love lazy Sundays!) [MF]

This has happened one other time before today and we figured it was a stroke of luck, no pun intended.

It all started with my wife and I laying in bed on a lazy Sunday afternoon. She started playfully sucking my dick and I got really aroused. I think she could tell because she asked me to reposition myself before resuming and also massaging my prostate. I could instantly tell that something special was going to happen, my body started tingling and I was oozing precum into my wifes mouth like a faucet. As she looked up to tell me how much was coming out I grabbed my dick and started stroking it. Moments later I told her I was close and she took over with her mouth (she’s greedy and doesn’t like to waste) The build up was intense and before I knew it she was struggling to contain it all. She swallowed and gave me a quick once over for any overflow or leakage. I was trembling and my cock was still rock hard so I started stroking it just as she asked if I was going to cum again. I told her that I was and just as her lips wrapped around the tip I unloaded mouthful number two. This happened three more times! She barely came up for air because they were so close together, and the last 2 she just kept her lips wrapped around the tip as I stroked the remainder into her waiting mouth. She looked up at me with the look of amazement on her face and told me to try for one more. At this point I had completely exhausted myself and nearly drown my dear wife, all within 4 minutes from my first release. As she removed her finger from my ass she informed me that it was numb from milking my prostate the whole time. There we lay, me barely able to move a muscle in my body, my dick dripping residual cum, and her with no feeling in her finger and a stomach full of baby gravy.

[MT] First time anal with my college girlfriend. :)

My last post was a bit too kinky for some of you, so I thought I’d do something a little more vanilla – one of the earlier times we tried anal.

So my college girlfriend was a transwoman, and you can read more about her in my previous posts – she was gorgeous, with small supple breasts, big doe eyes, and an average sized, slim cock (5 inches long, ~4 inches circumference). In my first gonewildstories post, I described our first sexual encounter, and in the second, a kinkier cum-saving adventure. What I’m about to describe happened somewhere in the middle.

So after our third or so 69-cum swap adventure, we were laying in bed, cuddling, and Meg asked if I had ever considered anal. I told her my experience was pretty light – I’d tried sliding a finger or two inside myself a few times in the shower, but nothing really routine or anything. She responded, “Oh! Wow. How did you like it?” And I very quickly realized at that moment that what she really wanted was for me to top her, not for her to top me. I told her I’d liked it, but I didn’t really have the flexibility to do it comfortably with my hands. She giggled and told me she’d actually never done anything anal before, and hadn’t even considered topping a man. I think at this point I looked pretty embarrassed, but she was encouraging about it.

A night to remember Part 3 [MMFFF]

Part 2:

A night to remember Part 2 [MMFFF] from eroticliterature

I sat beside Alex and watched as Lisa slid her hands around Tricia’s back, to rub her hands over her belly. Julia stood in front of her, her hands rubbing her neck, shoulders, and breasts. Water sluiced over all three of them, the dual shower heads in the standing shower of our bathroom spraying warm water over them. Tricia had her head tilted back, her lips parted slightly in pleasure, as the two women rubbed their hands over her body. I’d pulled the standing doors off the shower to open it up, and water pelted out, but we’d covered the toilet and floor in towels to absorb the water. Tricia moaned lightly as Lisa’s hands found their way between her legs, rubbing back and forth across her thighs, and slowly began to move down as she crouched. Julia’s hands continued to wander her upper body, her motions smooth and delicate, barely touching, roaming her hands down Tricia’s arms, then back up to her chest and neck.

Shameful, Secluded Ravishment [Anal][Feminization][MM][Humliation] [xpost from a /r/dirtywritingprompts request]

I’d just turned eighteen the day before my flight crashed. Brett, the boy I crashed with, was nineteen. The flight was nearly empty and we’d been the only two in the back of the plane; it had broken free of the rest and we’d somehow glided and crashed in water. There had been a storm. It was deep wilderness. We had no idea where. We walked for seven days without finding the rest of the plane or anyone else. It seemed like we were maybe somewhere in Alaska–mountains and verdant forest stretching across what seemed like the whole world. We survived on water and very little food. On the seventh day we found the cabin. We figured it was some wealthy hunter’s cabin. The place was stocked with food, drinks, fuel, toiletries, a generator. It had pretty much everything you’d need to survive in the wilderness–except a functioning radio, any maps, or a compass. We settled into waiting it out for someone to find us in the cabin.

Shameful, Secluded Ravishment [Anal][Feminization][MM][Humliation] (from a /r/dirtywritingprompts request)

I’d just turned eighteen the day before my flight crashed. Brett, the boy I crashed with, was nineteen. The flight was nearly empty and we’d been the only two in the back of the plane; it had broken free of the rest and we’d somehow glided and crashed in water. There had been a storm. It was deep wilderness. We had no idea where. We walked for seven days without finding the rest of the plane or anyone else. It seemed like we were maybe somewhere in Alaska–mountains and verdant forest stretching across what seemed like the whole world. We survived on water and very little food. On the seventh day we found the cabin. We figured it was some wealthy hunter’s cabin. The place was stocked with food, drinks, fuel, toiletries, a generator. It had pretty much everything you’d need to survive in the wilderness–except a functioning radio, any maps, or a compass. We settled into waiting it out for someone to find us in the cabin.

[ff](mtf), Unexpected Interest [slow build][kink][tender]

Hello, and welcome to my wonderful wall of text. For boarding right to the sexy bits, “***” has been provided for your convenience. If you have the following sensitivities or turn offs, please take advisement that MyPoisonIsReddit is not responsible for any injury or suffering that may occur:

All the consent

D/s, Mistress/Slave

Impact Play

Anal Play

Degradation/humiliation (S*** mentioned)

Biting/Marking

Bondage

The Trans Agenda(TM)

Ironic Catholicism

My horrible sense of humor

This is the story of one of my most recent partners. As a bit of background, I’m a transgender woman. I started hormones a year ago, as soon as possible after my new insurance kicked in and a little after I turned eighteen. I’m tall, average build, and have some gentle curves and perky B cups. My hair and eyes are both a dark brown, and my hair is wavy and shoulder length, with natural red highlights. My genitals are still in their original configuration, although it’s become shorter and plumper, and I have a Midwestern accent that almost never comes out, but my domme tells me it can be sexy when it does.