Jet's First Double

Story Info
My friend's first double penetration.
1.4k words
4.02
67.5k
15
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My friend Jeanette had always wondered what it would feel like to have two men inside her.

Now, before I begin I should say that Jeanette (she goes by the nickname Jet) and I had been friends for years and, despite a couple of drunken fondlings, had never had a physical relationship with one other. We were great friends but our timing was always off: whenever she was in a relationship I wasn't, and vice versa. After nearly 4 years we'd finally figured out that our fate was just to be deeply intimate friends - but no more than that.

Which makes our experience at a Manhattan Beach party that summer all the more interesting. It was one of those late August beach parties that seem to last for a week, and we'd been having a great time together with a bunch of friends. The house itself was cavernous, with 2 large bedrooms on the top floor overlooking the beach; the downstairs floor was huge and it's where the guests were partying. I don't remember how we got onto the subject, but at some point we started talking about our past sexual experiences. She knew that I'd had a few 3 somes and, after she downed a very large margarita, told me that she'd always had the fantasy of being with 2 men.

Jet's a very beautiful gal - about 5'3", shoulder length blonde hair, green eyes, and a small-breasted, athletic body - and she's also very conservative. She worked in accounts payable for a movie production company, wore dark-rimmed glasses and pulled her hair back tight in a pony tail; when you saw her at work you'd say she was "pretty", but certainly not outwardly sexual. Truth be told, I didn't really think much of it - I just thought it was 2 people drinking and talking about sex.

But she wouldn't let it go. No matter what we talked about she kept coming back to it. She wanted to have a 3some. Her and 2 men. And she was quite specific: she didn't want one man behind, one man in front. She wanted 2 men INSIDE her. The more she talked about it the more animated she got; she seemed to take on a new demeanor, like she was giving life to some hidden part of herself.

Thinking I was calling her bluff, I finally said that I'd help her, that I'd be happy to share her with another guy. She knew I was straight, and I reminded her as much, and she simply stuck out her hand and shook it. "It's a deal," she said, then scurried off into the party. Haha, I thought - you get a bit of tequila in her and Ms. Accountant wants to talk slutty.

About 45 minutes later, Jet came back with James in tow. We both had seen James around the Manhattan Beach circuit - he was athletic and clean-looking, albeit a bit nerdy - and he seemed a bit nervous when he introduced himself to me. Jet said, very matter-of-factly, that James was going to help us with our project. "Huh," I asked, "what project is that?" I had forgotten about what he'd talked about earlier.

"The one where I get 2 men," she said.

A million thoughts raced through my head, the first of which was that it was all a joke, that Jet and James were just fucking with me. No no no, they both assured me, they were dead serious. After some awkward and half-drunken negotiations (James and I, both being straight, wouldn't participate with each other - just Jet), we finally gave it the "what the hell?"

Behind a locked upstairs bedroom door overlooking the Pacific Ocean, I sat and watched Jet and James begin. I sat in a chair across the room and watched Jet sit down on a beige chaise lounge while James stood before her; she began to suck him, slowly at first, but with increasing intensity and pace. Although I'd certainly seen my share of pornos, I'd never actually seen a naked guy in person fully aroused, and the sight of Jet sucking him got me amazingly excited. It was like I was watching my own private sex show, set against the backdrop of the Pacific Ocean.

After about 5 minutes, the couple changed places. James sat down on the chaise lounge, then laid back; he was flat on his back while his knees were bent and his feet firmly on the ground. Jet put her right knee up on the lounge, then swung her left knee up, straddling his waist; and with a slight turn of her head back towards me (making sure I was watching), she grabbed his glistening shaft, settled it between her now-soaked pussy lips.....and slooooowly sat down onto him.

I can't quite describe how exciting it was to see his shaft disappear inside her slowly, inch by inch. And I had the best view in the house, directly behind her.

Jet rode him for a couple of minutes, making sure to arch her back and give me a full, ample view of her beautiful pussy eating his shaft.

They got into a slow, steady rhythm. She would push up on her knees so it looked like his shaft would pull out but, just as it was about to, she'd sit back down onto him, stopping when her cheeks met his balls.

I stood naked behind her, as hard as I could be, and put my hands on her cheeks. Upon feeling my hands on her ass, she bucked slightly harder, as if the warmth of my hands energized her. I grabbed her cheeks fully, and when she lowered herself onto James her cheeks would spread, exposing her second hole for me. I stepped foward and settled my shaft between the crease of her cheeks, my length pointing up towards the ceiling. As she felt my length along her crease she bucked harder onto James, enveloping and caressing my shaft between her beautiful cheeks.

"Are you sure you want to do this, Jet?" I asked.

"Fuuuuuuuck yes," she moaned, her voice low and grainy.

I touched my index and middle fingers to my mouth, inserted them to get them nice and wet, then removed them and touched her cheeks. Swirling my fingers around her second hole, I lubricated it then firmly grabbed her ass cheeks. I settled my swollen head at her opening and let it rest, allowing her to dictate the rhythm and pace of my entry. James lay under her while she jammed down onto him and Jet, upon sensing me at her opening, gently leaned back into me. I held her in my hands but didn't pull her back onto me, and Jet pushed back.....back......back......she let out a deep "unnnnghh".....then paused as my head disappeared just inside her. All 3 of us stopped moving. Jet just sat immobile, one cock in her pussy from below, and my cockhead inside her ass....just my tip.

I'll never forget the look on her face I saw in the window reflection. Jet was looking directly at me in the glass - her eyes staring deeply into mine - and she was breathing heavily. I could see her back arching with each deep breath she took, and small beads of sweat had formed on her lower back. And then, when she was overcome with desire, her eyes closed, her head threw back and her mouth gaped open. As she pushed herself back fully onto my shaft, she gasped as both men filled her up completely. What surprised me the most was that I could actually feel his shaft inside her as well as she swallowed us both up; it actually felt like I was fucking her with 2 cocks.

I put one knee up onto the lounge for balance and grabbed her hair lightly, pulling her head slightly back. I didn't even thrust at all, I just steadied myself and let her pummel into me. The sight of my beautiful accountant friend turned total slut was indescribable. When she came - and when she coaxed the cum out of both our cocks - she was completely, utterly, totally silent. Although her mouth gaped like she was screaming, she didn't utter a sound. She was completely transformed, her hungers slaked.

I lost touch with Jet over time, but saw her a couple of months ago at a local Southern California restaurant. I asked her if she'd stayed in touch with James - she hadn't - but she smiled and said that it didn't matter. She hadn't wanted anything more. She'd just wanted to know what it felt like to be filled.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
Steve OrshonSteve Orshonover 17 years ago
I Liked It

This was a little short, from the minimal character development to the sexual build-up and execution. It almost seemed rushed.

The overall theme was pretty good and the setting believable; it's just that the author didn't really take the time to make this story great. Still, if you like to read about quiet girls that go wild, this works.

AlhazredAlhazredover 17 years ago
Some idiots

Why idiots who obviously don't like the idea of anal sex choose to read a story about double penetration is a mystery.

A good story, well written, if a bit short. The only "problem" with the story, per se, is the ease with which the woman in the story takes two men at once for the first time. I've never known it to be that easy at first, but experiences vary and I understand the need for creative license for the flow of the story.

Overall, well done.

Share this Story

Similar Stories

Bachelor Party Gang Bang Wife strips at bachelor party, gets more than expected.in Loving Wives
Wife's Unusual First Time Wife feels sorry for a younger guy she later fucks.in Loving Wives
Birthday Boners My wife wanted double penetration for her birthday.in Loving Wives
Plugging Katie's Holes My slutty friend puts out for her three fuck buddies.in Group Sex
Pushing Boundaries Strip Poker on Roommate Bonding Day.in Group Sex
More Stories