Becky's Bucket List

I've always liked online chatting. There is something liberating about anonymity that makes people more comfortable to talk about themselves in an intimate way. I enjoy the idea that most people you see every day are just like you and enjoy playing with themselves just as much. 

Needless to say I have spent many evenings meeting and chatting with some fun people who proved to be like minded and open about selfpleasure.

This was how I got to meet Becky. We both had a profile on a site where you could post nude, selfmade pictures. Seeing each other naked is a surprisingly good icebreaker. But, besides being just horny people, we also had a lot of things in common to talk about. A lot of people you chat with come and go, but Becky was good company and it was always a pleasure to see that she was online. We would talk about anything and everything and were never shy to touch private subjects. 

It didn't take long for us to know each other's fantasies. It weren't so much fantasies as such, we considered them mostly "bucket lists". 

Our bucket lists were a list of things that we just didn't get to do yet. Things that were maybe weird to bring up in a conversation with someone you cared about. We didn't even considered them to be sexual. 

It all started during one chat where I admitted that I was stroking myself. That wasn't the first time, offcourse, so Becky was quite casual about it. 

"What are you jerking off to?"

"Some shemale porn."

"Again? You should do something about that."

"What do you mean?"

"I don't know, get some chick to fuck you."

"Yeah, like that will ever happen."

"Who knows, maybe some day? Can I watch you cum?"

"I thought you would never ask." 

With that I disconnected my webcam from my monitor and put it on my table. It almost became a routine already; clearing the desk, setting up the light. Becky made herself comfortable and got ready for the show.

"Are you ready?", I asked Becky who's eyes were glued to her screen. 

"I'm always ready for some cum!", she laughed as she clapped her hands.

I was edging for quite a while, so I was good to go. I pulled back on my cock one last time, trying to get everything on cam. I couldn't help letting out a small grunt as the first stream of cum shot out of my cock, splashing on my desk, followed by a second, and a third. I laughed a little as I tried to catch my breath. Becky was happy and applauded my efforts. 

"Clean up on isle five!", she laughed as I grabbed my paper towels to clean the cum off my desk.

"Do you cum more when you jerk off or when you fuck?", Becky asked.

"I don't really know...I guess when I edge a lot it gets more built up and there is more. You never noticed a difference with your boyfriends?"

"None of my boyfriend's ever jerked off for me."

"Wait, what? You've never had a guy jerk off for you? Seriously?"

"No, we always just end up fucking, I guess."

"That makes sense."

After an uncomfortable long pause I had to ask; "would you like to see sometime?"

"What, in real life? A guy jerking off? I guess I would, but not just some random stranger."

We both knew exactly where this was going. 

"I guess you're always welcome to come here for a drink...", I offered hesitantly.

This was crossing a line. We were online buddies, never destined to meet in real life, that's what made it so comfortable, and now I was changing everything. I hoped she would decline the invitation, it was probably a bad idea.

"Sure! Why not?" Becky sounded confident, but I knew she must have had the same hesitations.

"Are we really doing this?" I asked just to be sure, but Becky's mind was made up. This Friday a woman, whom I had never met in real life, would come over with the sole purpose of seeing me jerk off.

When that fateful Friday arrived I was understandably nervous. I didn't actually know this woman who would visit me in my home. I figured she was just as nervous as me, so I made sure my house was as welcoming as I could get it. I had drinks ready, some snacks; exactly what I would expect to find if I were to visit some stranger to see him jerking off.

When the doorbell rang all nervousness was gone; this was was happening. For the first time I saw Becky in real life. I knew she was older than me, but she aged well. Obviously she used some filters on her profile, but she was still a sight to behold. 

Not knowing how to greet each other we awkwardly shook hands as I invited her in. I took her coat, as a gentleman, sat her down and asked her if she would like a drink. 

"A white wine, if you have any."

Of course I did, with my expectations for this evening, did she really think I would forget her drink?

We got comfortable and I asked her if her trip was ok. 

"Do you feel like jerking off for me?" Becky blurted out. I was not ready for that candor. 

To try and keep up with her nonchalance I just unbuttoned my pants and took my flaccid cock out. Becky was quite familiar with it by now, but it was the first time the both of them were in the same room, so to speak.

Becky brushed my cock with her finger with the same level of nonchalance as we shook hands minutes before. As she did this she just laid back on my couch, ready for a show. She was wearing a short skirt that rode up as she spread her legs revealing her red panties. 

"What are you going to jerk off to for me today?" Becky asked, almost vulgarly.

"What do you want me to jerk off to?", I asked, trying to match her forthrightness.

"Shemales!" She cheered.

"As you wish."

I had to reach over to my computer to find a good file. With a click of a button the video played on my tv. As I reached over we were both aware of my nudity; my cock in my hand, my ass bare out of my pants. 

I sat back down and made myself comfortable, slowly stroking my cock to it's full hardness. My eyes were glued to the screen, as I felt hers on my cock. The video started, showing a beautiful shemale slowly stroking her cock, just as I was stroking mine.

"Are you liking this?" Becky asked, clearly liking the show.

"Yeah...she's so hot, just look at her!"

Becky reached over for her purse and seemed to be looking for something. After a second she pulled out a dildo. 

I was not ready for this, but tried to focus on the video. "Don't mind me." she reassured me. She was inspecting the dildo, it had two ends to it. She found the smaller side and aimed it towards her red panties. In a flash she pulled her panties aside and pushed the small side inside her. I had seen her pussy before, but seeing her do this almost chocked me. 

"Keep on going!", Becky demanded, as she slowly started jerking off the dildo that was sticking out of her. 

Between the video I was watching and the show that was playing right next to me I knew I wouldn't be able to last much longer. I was beating my cock in a rate that was unfamiliar to me, I needed to cum! "I...need to cum! Where do you want me to cum?" I gasped. 

Without a second thought Becky kneeled down before me and opened her mouth. As if I had any choice I released my cum. The first stream went on her face, but as her mouth covered my cockhead I can't remember how much went in the mouth of my online friend.

She wiped her mouth while I was coming back to earth. "Was that ok for you?"

"That was amazing!"

"No-one ever did that for you before?",  I asked.

"Never!" She smiled as she was still holding her dildo. "How about you show me your bedroom?"

I was almost chocking from excitement. "It's right over here", I said rushing up.

"Hang on, I need to pee first."

I looked her straight in the eyes...

"Can I watch?"

There were no inhibitions between us.

"If you like"

Becky found my toilet, and as I watched she carefully spread her lips and let out a trickle of golden pee. I had never seen anything like it, but it was mostly funny because I was sure she never showed anyone either.

By now we knew that there were no inhibitions. I was on my bed as she walked in, reinserting her double dildo. She was stroking it proudly. It was obvious that she knew what I was expecting.

"Are you ready for me?", she asked, while holding her cock. "Are you ready to get this off your list?"

"Let's do this slowly!" I suggested, not curtain where this was going.

I raised my ass up as an invitation. "Try a finger first...romance me first." I felt Becky getting closer and spreading my cheeks. The first finger went in with no problem, neither did the second. But when she started pushing in the dildo I realized that this was too much for my virgin asshole.

"Wait wait wait! I think this is a little too much!" I pushed her back a little. "Let me try this first." I laid back with my legs spread and slowly aimed the tip of the dildo towards my ass. It only took me a little push to come to the conclusion that this would never fit.

In the meantime Becky was enjoying watching me fumble. The was rubbing her pussy while watching me. 

"Come on! Are you sure?"

"Nope! I'm sorry!"

She was obviously disappointed. I was trying to position myself on the piece of rubber, but to no avail. 

Becky grabbed the dildo from me and, while she lifted her legs she aimed it towards her own ass. She shuddered a little as the head of the dildo slid in her ass. I was impressed, when she tried to put it in me I didn't stand a chance. But here was Becky, slowly pushing her cock inside of herself. 

It took me a minute to realize what I was watching as I could feel my cock harden. Becky looked down on me as I was, almost asking me to take the next step. 

I carefully took hold of the dildo, freeing her hands to stimulate her pussy. As I slowly pushed it in her I couldn't help stroking myself at the same time. I had an orgasm not too long ago, but seeing this marvelous woman before me, trying so hard to prove she could insert this piece of rubber in an orifice I also had was too much for me.

As the dildo kept penetrating her both Becky and I kept masturbating ourselves to the uniqueness of this situation. I wished I could have kept stroking my cock for days enjoying the view of her rubbing her pussy in front of me while I was pushing this piece of rubber inside of her. But, offcourse, it couldn't last forever. 

I moved up, rubbing my erect member against her breast, and with a last spasm I shot my cum against her breasts. For the second time that evening Becky witnessed a guy jerking off for her. As I did the honors I felt a small trickle against my leg, informing me that I wasn't the only one who came in my bed that evening.

We lay there for a minute, trying to recover from the events, giggleling a little.

We worked off some more things of the list and the next morning she went home again.

It was a lot of fun, but we both felt this was a one time thing, just to get the pressure off.

We still laugh about it on chat...