Me [M], my friend [M], and my ex [F] (Long) | 2016

This is a combination of five different updates I posted in /r/jobuds. The updates are compiled below. This is long — my apologies.

Part I

In high school, I dated a girl named Amy. Amy wasn't a great student, honestly wasn't the smartest person in the world, but was nice, fun and, unbelievably hot. She had dirty blonde hair, the most amazing boobs, legs and a tight, firm ass. Her boobs would range from a 36-C to 36-D depending on her diet. She also had these giant pink nipples that i just loved.

I was with her because she was hot. Eventually we broke up and I departed with about 150 naked pictures and one video of her that I had filmed during our days together. I asked her to delete the photos that I had taken for her and she obliged. I asked her if she wanted me to delete them and she told me she wanted me to keep them and "Do whatever you want with them" because in her mind, they were my pictures ("gifts" is what she said).

I kept them on an password protected external drive and my phone using a photo-lock app. Not going to lie, over the last two years, I've probably jerked off to her hundreds of times.

Today, I'm 21 years old. Over the last two years, my group of friends have often tried to get me to show them pictures of her. Again, she's hot and they knew her when we were dating. They've offered me money, pics of their exes, etc. I've always said no.

Recently, I changed my mind. I have one friend — Keith — who I trust more than any of my other friends. He's also been the one who has been the most persistent in trying to see those pictures. He's the only one that went to high school with Amy and I, so he's known her the longest. Like most guys who went to my high school, he was also obsessed with her. He once admitted to me that he used to jerk off to her bikini facebook pictures during high school.

I decided I wanted to surprise him and show him those pictures. But I didn't just want to show them on my phone in their standard form — I wanted it to be an awesome experience.

So, I decided to make a movie (I'm studying film). Keep in mind, I only have pictures and one video, so essentially it's just a slideshow with effects, music, etc. Without going into too much detail, I ordered the pictures in such a way so that the pictures get more revealing as the movie went on, thus teasing him. It's only about halfway through that you can see her nipples. At the end of the movie, the video plays. The video is roughly 6 minutes of her jogging naked on a treadmill, doing jumping jacks, lifting weights, in my home gym.

But, before I showed him the movie I wanted to tease him a bit more, so I made a trailer. Basically the trailer showed some pictures of her that were censored and then showed clips from the video, but I also censored out her tits and ass.

I put both of those files on a flash drive and drove over to his house to hangout with him and some other friends. I made sure that I was the last one to leave. Keith and I were drinking a bit when of course, the pictures came up like they usually do. Per usual, he tried to convince me to show him. To his surprise, I said "okay. Let's go to your room."

We connected his computer to his TV and I loaded up the trailer. I made him agree to never speak of this to any of our friends.

The idea was to just show him the trailer and then make him wait a day to see the actual movie. I showed him the trailer. His mouth was literally hanging open the entire time. And, I couldn't help it — I showed him the 15 minute movie as well.

He was in disbelief the entire time. He would point out ones in particular that he liked and we talked about her body the entire time. We watched it twice. Eventually I went home, but not after he had practically memorized her body.

Part II

Okay, so things progressed faster than anticipated. Last night, after posting the story, I went over to Keith's house to hangout. We were playing xbox for a few hours, when he asked me about maybe seeing the pictures again. I, of course, agreed. This time, his parents weren't home, so we hooked it up to his giant TV. As we were watching, I decided I was going to go for it.

It was maybe about three minutes in when I told him that I couldn't wait to go home and jerk off to this later and that I was so hard just looking at her. He shook his head and was like "man, you're so lucky you get to do that." I told him that he could just jerk off to her bikini pictures that he used to jerk off to all the time in high school. He told me that he probably would, but asked me if he could jerk off to the movie I made. I told him I couldn't let him be alone with the pictures, because he might send the movie to himself or take pictures of the pictures. So, he said he didn't mind if I was in the room while he did, but he just needed to get off to her. He said it would be a dream come true. I agreed, but told him that if he was going to, then I was going to also. He also agreed and left to grab us some towels and lotion.

We both sat on opposite ends of the couch and I started the movie again. We each got down to our boxers and started jerking. He didn't last long, he came well before the 6 minute video at the end. I finished shortly after.

We cleaned up, then started drinking and playing xbox again for an hour or so. wasn't weird at all, thankfully. It was about midnight, and I was pretty drunk, so I decided to text my ex. Here's a shortened transcript of our convo:

Me: Aye sup?

25 minutes later...

A: Hi!!!! Sorry I was drinkin at Jesse's house and just got home, bout to netflix you? Me: Drinking with Keith. You drunk?

A: ha yah.... how s he?

Me: he's good, says hi and that he misses seeing you everyday in class.

A: Ha, tell him me too.

at this point, Keith is watching me text her. he tells me to tell her that we should skype now. being drunk, i agree.

me: so insted of watching netflix you shuld skype with us!

A: lol. i'm already in PJs!

Side note: when i was with her, PJs meant a wife-beater with no bra, and a pair of regular underwear.

me: c'mon, we don't care if you're in pjs. I've already seen you in pjs millions of times.

(more convincing)

A: fine. lemme get my computer.

So, we eventually skype. I'm right about her outfit. Can't see below her waist. the conversation is mainly me and her talking, with keith kinda chiming in. nothing is really happening, she's drinking a beer, so are we. it's kinda flirty, but a lot of catching up, when her phone rings behind her on her bed. boom! she gets up and walks over to retrieve it, in the process revealing her ass in a pair of normal underwear (some things never change). She actually bends over to retrieve her phone and then she's back. at this point, keith takes out his dick because she can't see anything below our chests and he's mildly playing with it.

she acts like nothing happened once she gets back to her chair. we talked for a bit longer than eventually she said she had to go to sleep cause she had work in the morning. She logged off and Keith and I watched the video one more time and jerked off.

Part III

So, since that first skype session, two nights have passed.

The first night: Our group of friends were going bar hopping. Keith and I, decided to skip, telling them we didn't have money to spend at bars (partly true). So, instead I went over to Keith's. Per usual, we started drinking. This time, instead of playing xbox, I put on the movie on his TV upstairs and we just sat there, watching and talking about her. Pretty soon, both of us were jerking off to her. We both finished and I decided to text Amy again. I'll save everyone the play-by-play, but eventually we got on Skype again. Yes, she was wearing her tank top again without a bra. But nothing really happened. There was some more flirting and Keith actually talked more, which was a positive, but eventually she wanted to go to sleep instead of talking to two drunk dudes. Anyways, that was pretty much the end of the night.

The second night: This is where things got kinda interesting. Keith and I are hanging out after everyone else leaves his house. We start drinking and I'm about to put the movie on when Amy texts me...

Amy: Heyyyyyyy

Me (with Keith looking over my shoulder): Hey. What's up?

Amy: Im drinking. At home. By myself. Is that bad?

Me: Nahh it's not bad, me and keith are drinking too. What're you doing at home?

Amy: Got a fifth of vodka and binge-watching Friends haha.

Then, a double text...

Amy: You guys wanna get on skype?

Me: Yeah! Hang on.

Of course, keith and I basically sprint over to the computer. We log on.

This time she isn’t wearing her normal tank top. She’s wearing a pink tube top. A bra too — we would definitely be able to see her nipples if she was braless. And again, idk what she’s wearing below her waste.

We start off talking like usual and she’s drinking from a cup. We ask what’s in the cup, she says vodka and sprite. She notices that Keith and I aren’t nearly as drunk as she is and says something along the lines of: “you guys need to get more drunk like me!” (i know her pretty well, i don’t think she’s drunk yet, but she’s definitely buzzing.)

So, I happily suggest a drinking game. Keith and I had talked about this already, and he suggests truth or dare. Drink if you refuse to answer a truth, drink if you refuse to do a dare. She agrees immediately, but says we have to switch to something other than beer. Keith runs downstairs to grab some vodka. We mix drinks and the game starts.

(side note: i might have some of the exact details jumbled, but i’ll do my best to get it right).

We decide right away that me and keith are basically going to be one person throughout the game, so she dares both us to do stuff, or asks us the same question and me and keith combined only get one question/dare per round.

We say dare first, and she tells us to add more vodka in each of our drinks. We oblige. For her turn, she says truth. We ask her “what’s your favorite sex position.” She thinks, then says cowgirl with a wicked smile on her face. (side note: this was my favorite position when i was with her. girl knows how to ride... hard).

Our turn again, and we say truth. She of course, asks us the same question. I say cowgirl. Keith says doggy. She opts for truth, and we ask her how many guys she has slept with. She decides to drink instead of answer. We decide for dare, and she dares us to take off our shirts.

obviously, we do that. And now, we’re both really happy because she’s the one who made the first move. She says “Dare,” and we dare her to take off her shirt. She drinks.

We say truth, and she asks us to tell her what we think her best feature is. Now, she doesn’t know that Keith has seen her every feature. We both say her boobs.

She says dare, and again we dare her to take off her shirt. She drinks. We say dare, and she dares us to take off our pants. We oblige, but remind her that she can’t even see below our waist. Kieth and I are now in our boxers. She says dare again, and we again, dare her to take off her shirt. She almost drinks, then says fuck it, and whips off her tube top. She’s wearing a strapless bra underneath, since her tank top was also strapless. It’s gray. Keith and I are rock hard at this point.

We say truth, and she asks us if we like what we see. We both nod, eagerly. She says dare again, and we tell her to take off her bra. She smiles at us and then without saying anything, turns away from the camera. She takes off her bra and let’s it fall. Then, she turns around, but her right arms is placed over her tits, acting as a bra. Keith and I are hypnotized when she, with her other arm, tilts her computer up so that the bottom of the screen is at the very top of her breasts. Then she, releases her tits, now that we can no longer see them. Essentially, she is topless and isn’t covering her boobs, but we can’t see them. We argue that isn’t fair. she just smiles at us and says you guys wish.

We say truth, and she asks us if we’re both hard. We say yes. She says dare. and we dare her to tilt the screen down. she says ok. and reaches for the screen. instead, of her glorious tits, our feed is gone and she’s offline. She texts me, “Sorry ;) …. don’t worry, i drank after my turn.”

I texted her for a bit trying to convince her to get back online, but she just said she’s going to bed and said that she hoped we enjoyed the show. Keith and I jerked off to her movie and then I went home.

Part IV

Alright guys. I’ve been really busy today (more on that later) and haven’t had time to write the third update, but here it is. A lot has happened since.

So, we skyped again last night. I had been texting her on and off since the last skype session, when last night she texts me and asks me if Keith and I want to hangout on Skype again. She finishes her text with: “We can pick up where we left off.”

Immediately, I call Keith and ask if he’s free. He is, so I head over at like 10 pm. I text Amy to see if she’s ready to Skype and we get online with her.

This time, she’s wearing her normal night time attire — wife beater and no bra from the looks of it. Can’t see what she’s wearing down below. She asks if we want to play truth or dare again. We both say yes. She says she wants to raise the stakes. She wants to make it just dare and no truth. And, if we don’t do a dare, we have to do a shot. Of course, we agree.

(we’d probably agree with anything she says at this point).

She starts. She dares us to do two shots each. We oblige. We (of course) dare her to take off her tank top. She does a shot. She dares us to take off our shirts. We take them off. We dare her to take off her top. She does a shot. She dares us to take off our pants. We do that. We dare her to take off her pants. She says she isn’t wearing any pants and stands up to show us that she’s wearing a pair of pink panties. So, instead, we dare her to take off her panties. She does it, though we can’t see. She dares us to take off our boxers. We do it. Keith and I are both naked now, and we’re rock hard.

So, since she hasn’t been very keen on taking off her shirt this round, I instead decided to dare her to walk away from the camera until she reaches the far wall of her room and then to walk back. And……she does it!

She walks extremely slow, moving her hips in a exaggerated way. Her bare ass looks fantastic. It's so firm and pretty big for being so tight. Then, when turns around, we see that she is completely shaven. Though, because of picture quality, it’s not like we got a great look of her pussy. She dares us to do the same thing. Except, she wants us to walk backwards and then forward, so we’re always facing the camera. Keith and I both do it, exposing our cocks to her.

For the sake of detail, I am roughly 5.5-6 inches when hard and I’d guess Keith is probably about 6.5 or 7 and a little thicker. We’re both circumsized.

Anyways, we get back to our seats and sit down. We dare her to take off her shirt. She drinks. She dares us to stand up for the remainder of the game so that she can see our bodies too. We do that. So now, Keith and I are naked and standing in front of a camera. We're also rocking huge boners. She’s bottomless but we can’t see her bottom anymore. Again, we dare her to take off her shirt. This time, she turns around and takes off her tank top. She turns around and is covering her tits with each of her hands. Keith and I are still so fucking hard.

She looks at us, and tell us that this is her final round. She dares us to “Come over tomorrow and hang out with her.” We say yes of course. She says “okay, see you guys tomorrow. Come over around 11 tomorrow morning.” She’s still covering her tits. We say okay and then remind her that she started the game, so therefore we get one more dare. She says okay, and we dare her to drop her hands and let us see her tits. She says no, I’d rather drink. Then proceeds to pick up her bottle of vodka with her hand, thus releasing one of her tits, then grabs a shot glass with the other hand. Both of her tits are on full display when she pours a shot and takes it. She’s now completely naked and we can see her tits. Then she stands up and turns off her feed.

Keith and I are stunned and jerk off on the spot. We didn’t even use the video but we each cummed in probably 30 seconds or so.

Part V

Keith and I decided to grab some breakfast before heading to Amy’s house so we could talk over some stuff. We met at about 9:30. Over breakfast we talked about certain things like condoms (We brought them just in case) and alcohol (we figured she would have some there. we’re poor, so don’t judge.)

I also tell Keith about Amy’s house. As mentioned earlier, she wasn’t the best academically. She doesn’t go to school. She works a part time job at a restaurant type of place. She lives off of her dad. Her parents are divorced and she lives with her dad. Her dad is fucking loaded. Their house is insane. It’s huge. She has a pool, a hot tub, a sauna, and a steam room. Her dad is usually never home and is away on business a lot. Amy and I had a lot of fun in her pool, hot tub, sauna, and steam room while we dated.

Keith knew all of this, but I wanted to remind him of all the things that could maybe happen. Keith wanted to know if we should have brought swim trunks, but I reminded him that us not having swim trunks might be better and lead to naked type of things.

So, we eventually drive over to her house. We ring the doorbell and she opens the door. She’s wearing jeans, a black v-neck. It’s a pretty deep V but nothing outrageous. I won’t lie, I was hoping she would open the door in a bikini or something, so I’m a bit disappointed. She invites us in and asks if we want a drink. We say yes and she proceeds to mix us some pretty strong vodka sprites. She makes one for herself too.

We’re kinda standing around drinking, when she asks us what we wanna do. I ask her what she wants to do and she says she was thinking about tanning and we’re welcome to join. Keith and I both say we don’t have swim trunks.

“But you guys can just tan in your boxers, right?” Amy says. We agree and then she tells us she’s going to head upstairs to change into a bikini and that we can go out and get started without her. She tells us to grab some towels on the counter.

So, once she heads upstairs, Keith and I strip down to our boxers. I’m wearing normal boxers with a slit in the front, but the slit is buttoned up. They’re grey. Keith is wearing white boxer briefs.

We grab our drinks, towels, and head outside to the pool. There are a few beach chairs lined up and Keith and I strategically sitting down with a chair between us. That way Amy will be situated in the middle of us and one of us isn’t screwed out of seeing her body.

It takes about five minutes and the Amy pops outside. Her bikini is fucking RIDICULOUS. I spent a way too much time googling, and while I couldn’t find an exact match, it kind of looked like this…

The top: http://www.teenyb.com/Products/Classic-Butterfly-Top-in-Black__222-7020-91000.aspx

The bottom: http://www.teenyb.com/Products/Classic-Brazilian-Half-Pucker-in-Planet__222-7030-41500.aspx

“Hey boys,” she says when she sees us. We mumble something back.

So, she grabs the chair in between us and reclines it all the way down. She sets her drink on the table between my chair and hers, and lays on the chair, with her head down. Now, I didn’t have the balls to say this or didn’t think of it, but Keith says the most obvious thing to say in this situation: “Do you have any sunscreen?” It also made more sense for him to say it because he is really really pasty and actually needs it.

She says it’s inside on the kitchen counter and that she forgot it and she asks if Keith can grab it. Keith gets up and walks inside. As he walks by I notice a tent starting to form in his boxer briefs. Amy also notices…i think. Keith returns and sits down on his chair. He starts putting on sunscreen on his chest and legs. Amy, who is now laying on her side and is facing Keith, asks if he wants her to do his back. He says “Sure” and also reclines his chair all the way down. Amy straddles his butt and begins slathering sunscreen on his back. She finishes and asks if I need sunscreen on my back. I say yes and lay down and she slathers me up with sunscreen. Nothing too terribly sexual since it’s our backs, though her hands did feel nice.

She finishes and I grab the sun screen and do my arms and chest. She is sitting there, looking kinda impatient, when she finally asks if someone can do her back. Keith beats me to it and says he can. She lays down on her back and Keith is sitting on the edge of his chair and starts to rub in lotion. He’s rubbing it in the middle of the back when he moves his hands up towards her bikini straps.

Amy says, “Hold on! I don’t want to get sunscreen on my bikini. Can you untie it?” Her head is still down.

Keith looks at me in disbelief — he now has a raging hard on — and unties both of her straps and the straps fall to the chair. He massages the lotion into her but doesn’t really make a move. I myself wondered why he didn’t try to get the sides of her boobs. He then turns to her legs and starts at the bottom, working his way up. He pauses as he gets to her ass cheeks which are partly hanging out from her bikini bottoms. She doesn’t say anything, so he proceeds to rub her cheeks down with lotion. He finishes, she mumbles thank you with her head still down and Keith and I both sit and stare at her ass. Keith is pretty much in disbelief, he never thought there’d be a day when he got to massage Amy’s ass.

She lays down like that for awhile, maybe 20 minutes or so, occasionally taking sips from her drink. Her bikini is still untied, but she makes sure her tits don’t slip when she drinks.

Keith and I both now have our chair at a more upright position, maybe at a 45 degree angle so we’re able to see her body. “Alright," she suddenly announces. "Time for me to flip. Keith can you tie me up.” I inwardly groan, i was hoping she would tan topless. Keith ties her up and she flips over and starts slathering more sun screen on her front. Now, she definitely notices our boners.

After a bit more of tanning, she gets up and asks if we want more to drink. And then she leaves to make us all drinks. Keith and I look over at each other and are like holy fuck. What now?

At this point I’m not really sure how to make a move. When Amy appears with drinks, I suggest a dip in the hot tub. Amy, instead, says "let's do the sauna." At this point, we won't argue. We make our way over to the sauna — it's a wooden, outdoor sauna, so it isn't attached to the house. It's near the pool. When we get there, it's Amy who makes the first move.

"You guys probably shouldn't wear your boxers in there. You don't wanna sweat out your boxers," she says. Then, she opens the door into the sauna and leaves us outside.

Keith and I look at each other. I say: "She's actually right." Keith and I shrug and basically say, she's us naked before. We take off our boxers, leave them on the ground, and head inside.

It's a pretty small sauna, with really only one bench to sit on. It's more than enough space for all three of us. She's sitting there, right in the middle, rocking her unreal black bikini. We both enter and we're both rocking boners. Again, I'm around 5.5-6 inches and he's more around 7 inches. He's also a bit thicker. We're both circumcised. We're also both pretty well kept down below. Neither of us are completely shaved, but we don't have much hair. Ever since we've started skyping, I've been trimming every day.

When we enter, she's openly staring at our hard cocks. We both sit down next to her. Again, she's been making all the moves so far so I'm waiting for her to make a move. She doesn't....really. Well, she stretches her arms upward, showing off her stomach and tits. We're sitting there, making small talk, when suddenly she begins openly talking about our dicks.

"It's been awhile since I've seen you like this," she says to me. Before I can say anything, she turns to Keith and says, "You know I wasn't kidding about your dick. It's really impressive."

Keith is literally speechless. Both of our dicks look like they're about to explode.

She turns to Keith. "Can I touch it?" Keith stammered a yes or something that sounded like it. She places her right hand on Keith's dick and begins feeling him. She begins slowly jacking him off, building faster and faster. Suddenly, her other hand is on my dick. She turns to me now. "I wasn't going to leave you out. I know how much you love my handjobs," she says. She begins jerking me off too. Even though she's using her left hand, I know I'm not going to last long. I tell her I'm going to cum soon and Keith begins groaning. Suddenly, Amy stops and releases our dicks. We both look at her in confusion. She doesn't say anything and instead walks out of the sauna, leaving us there, so close to cumming.

We follow her out. I say to her: "c'mon, you can't do that to us! that's not fair." She looks back and says, "sorry guys. My dad is going to be home from work soon. And i need to shower."

Keith chimes in: "You gave me blue balls though." Amy considers, standing puzzled. She then offers us a deal. "How about I shower using the outside shower, and you guys can watch and jerk off?"

We agree. Amy walks over to the outdoor shower area (it's like a little rinse off station) and strips off her bikini. She's completely naked and she's washing herself. Keith and I walk over to her. We're just a few feet away, also in the shower area, and we start stroking our dicks. Amy is watching us the entire time. Keith cums first. I watch his cum hit her on the leg. He hits her again with a 2nd spurt, though it's quickly washed away. Seeing that is more than enough, I cum and I hit her in the lower stomach 3 times (I've never cum that much in my life). Again, the cum washes away. Amy still keeps on showering, rubbing her tits more than anything else. Keith and I are spent.

We keep watching and eventually Amy turns off the shower and wraps a towel around her and heads inside. "You guys should go," she says. "My dad might come home soon." She says some other good bye then disappears inside.

Keith and I put on our clothes and we head home. We talked on the phone just before i wrote this, and we're still in disbelief. And we can't wait to see where this goes from here. She still hasn't made us cum, so I think there's more to, well, come. Hopefully.