Holodeck Discoveries Ch. 02

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Guy encounters a kinky beautiful woman masturbating.
3.9k words
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Part 2 of the 3 part series

Updated 06/07/2023
Created 09/27/2015
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This story is set in the Star Trek universe, but does not feature any of the familiar characters you may have seen on TV. However, it does mention some events which may be familiar to fans of the show. However, no copyright infringement is intended. This is a work of fiction from my imagination and fantasies and does not have anything to do with Star Trek or its creator etc.

As per my usual, this story is more of a slow burn than a slam-bam-thank-you-ma'am, but when it does reach its climax, I hope you do too dear readers. I'd love to hear about them in the feedback.

This story has (hopefully) something for everyone because my own fantasies and kinks are so varied. It features M solo, F solo, Voy, MM, MF Intr, FF Intr, MFF Intr, MMF, NC, MF Inc. Enjoy!

*******

First Engineer's Log; Star date 63224.2

I am in the process of describing the events that have happened since I boarded star base 12 almost 6 months ago; how I met the sexy Ensign Gordon, how I found some memory chips hidden behind a panel in the warp core we were in the process of restoring, and how I accessed those chips and got the surprise of my life.

To be honest, I'm still unsure why I'm recording all this in my log. I may yet delete it, but I did find that talking about my colossal blunder with Anessa, and being anally raped by a Holodeck program did help, so I'm going to continue logging it.

So I had just been raped by a large man on the Holodeck, during which my uniform got destroyed. Now I had to get from the Holodeck on deck 15 down to my quarters on deck 8 without being seen.

******

I peeked around the corner of the corridor leading to the turbo lift. It, like the other corridor leading away from the Holodeck, was blessedly empty. I rushed to the turbo lift and pressed the call button.

The lift arrived and the doors swished open and my worst nightmare was realized; the Admiral, my sister, my nieces and Anessa were all in the lift together! They collectively stared at me and my shredded uniform, their expressions ranging from curious and confused (my nieces) to angry (the Admiral). Anessa, I noticed, could not look me in the eye at all. Time seemed to stand still as we all looked at each other. I was rooted to the spot. Then the doors closed, while I remained standing in the corridor, naked from the waist up.

I counted to 10 and pressed the call button again. A minute later, the lift arrived, and this time it was thankfully empty. I returned to my quarters without further incident.

I stripped down, disposed of my tattered clothes, then went in for a shower. Standing in front of my mirror, I surveyed the damage: my nose was red and swollen, I had a fat lip, and I had bruises on my ribs where he had punched and kicked me. However, the worst discovery was the dried cum that was caught in the hair around my navel because that was also the point when I remembered that my navel had been clearly visible to everyone in the turbo lift.

All told, not a great day. But strangely enough, it was a great day. I had just experienced the single most thrilling sexual experience of my life.

I hopped in the shower and got cleaned up, then got dressed and sat down at my computer terminal. Despite all the recent turmoil, I realized that I wanted to know more about this Annette and why she needed to have such violent sexual experiences on the Holodeck.

First, I searched the records of personnel who served aboard the USS Melbourne. The search results came back null. Then I remembered that the core had been stored on Titan for almost 200 years. I searched the records of Starfleet personnel stationed on Titan for the last 200 years and again came up with nothing.

Finally I searched for everyone named Annette who had been on Titan between 150 to 200 years ago. My search returned 2 names: Annette Hamilton, who had stayed there for 1 week to visit a relative, and Annette Fellowes, a janitor who had spent three years working at the storage facility. I figured she was the likely creator/owner of the chips.

I pulled up her file. Annette Catherine Fellowes had been 25 when she first got posted to Titan. She worked for Castlecorp, a firm that had a maintenance contact with Starfleet from star date 42566 to 55634. The youngest of three, her two older siblings served in Starfleet. She also had a few brushes with the law in Cleveland, her home town. Looks like she had been involved in some trouble on Titan too and eventually got transferred to Deep Space 9. She died in a bomb blast on that station, just shy of her 35th birthday. Never married.

I pulled up a picture of her from her employment records at Castlecorp.

I was startled by the face that stared back at me from the screen because it bore a striking resemblance to the man who had so thoroughly taken my anal cherry earlier today. Her shoulder-length hair was red, but she had the same dark hazel eyes and strong facial features. She was even sneering like him.

There was a ring at my door. I quickly closed up the information on my screen and responded. It was my sister.

"Tim, are you ok? You looked like hell earlier."

I launched into my cover story. "I'm fine Becky. I was trying out a new sparring program on the Holodeck earlier and my opponent beat me quite handily. It's nothing to worry about."

"It doesn't look like that to me Tim. Holodeck programs aren't supposed to leave bruises and split your lip. There are safeguards that are supposed to prevent injury. I know this because I researched it before letting Olivia and Sara go anywhere near the Holodeck on this base."

I didn't want to continue this line of discussion with her, but if I blustered or played evasive, she'd get pissy and eventually I would spill it. Instead, I used classic misdirection.

I asked, "What sort of programs do you run for the girls?" Then I listened to her go on for the next 20 minutes about what sort of programs my nieces enjoyed on the Holodeck. My sister is a wonderful cook and a fantastic mother, but she is not the most aligned phase coil in the engine if you know what I mean. Inwardly I breathed a sigh of relief at having avoided uncomfortable questions.

As I was seeing her out, she admonished me to go to sick bay and get looked after. I assured her I would and hugged her good night, finding my usual comfort in having her full breasts crushed against me.

I went to bed, suddenly tired. In the morning, I would find a way to apologize to Anessa, and also figure out what other information might be stored on those other 6 memory chips that belonged to Annette.

******

In the morning, I arrived at the hangar 10 minutes earlier than normal, coffees in hand.

Anessa entered the hangar at her regular time. She seemed wary and didn't greet me with anything more than a nod and a mumbled thanks for the coffee. The tension in that hangar was so thick you could almost see it.

Finally I couldn't stand it any longer. I cleared my throat and said, "Anessa, we need to talk."

"Oh do we now? Should we talk about how you overstepped your bounds and forced your tongue into my mouth? Or should we talk about how you show up at a turbo lift on deck 15 looking like you have just been thrown out of a moving vehicle? Save it Lieutenant. If you don't mind, I have align those pulse tubes."

"But please listen Anessa. I need to explain."

Maybe it was my earnestness, or the tone of voice, but she appeared to relent. She stopped and turned to face me.

I began, "Anessa, I'm so sorry about my unprofessional behaviour towards you yesterday. I have no excuse. I can assure you it will never happen again. I don't know what came over me, but from now on I will be nothing but professional. I'm so sorry. Our friendship and our professional working relationship is very important to me. I screwed up, and I'm begging you for a second chance."

The hard set of her beautiful features softened and she sighed. "Alright, I forgive you, but if you ever try something like that again, I'm going to Admiral Jacobson. And by the way, what the hell were you doing on deck 15 yesterday?"

I explained my breakthrough with the chips and how I had loaded up a violent Holodeck program. Obviously I left out the part about sucking that program's cock and being ass-fucked by said program. I also explained that I had determined the identity of the original owner of the chips. I then went on to tell Anessa about the little bit of info I had been able to dig up on Annette.

I just about swallowed my tongue when Anessa asked, "So when do we get to experience one of her simulations together?"

"Uhh we can't: I mean, what if it isn't safe? You did just hear my story about being attacked in the first program I loaded, right? I want to keep you safe. I don't want you to get hurt Anessa."

She wore an annoyed expression during my little speech. With some heat in her voice, Anessa replied, "I'm so glad you decided to keep me safe. Did it ever occur to you Lieutenant that I'm a big girl and I can handle myself? I will have you know that I ranked in the top 5 in my Starfleet self-defense class. Besides, I might be able to prevent you from getting hurt."

What could I say? I had no real reason to exclude her. "Ok Anessa. But let me examine the contents on the rest of the chips before we agree to run any more of her programs." I wanted to weed out any simulations that might try to rape us, and only allow us to experience 'safe' programs. But I wanted to do it in private so she wouldn't learn of my shame.

She agreed and we settled in to work. It felt good to dive back in to our task, and we soon fell back into our comfortable familiarity.

That evening, after another wonderful dinner prepped by Becky, I retired to my quarters and sat down to take stock of what was on Annette's chips.

After connecting the first one to the Tricorder, I pulled up the directory on the screen. This one featured 5 files: MOM, SOLO, BETH TOYS, KLINGON TIME, and STEVENGENT. The Klingon one sounded dangerous, while the ones titled Solo and Mom sounded fairly harmless. Still, I figured I should check them out on my own in case they were as bad as the first one I experienced.

I fired up the second of 6 chips. It had a folder called TRANSMISSIONS, which contained about 200 files that had dates for names. I'm sure these were probably messages that Annette had received up until the point when she concealed the bag inside the engine. The 3rd and 4th chips were too badly damaged to read so I threw those in the garbage.

The 5th contained three files: BETHSTEVE, MOMBETHSTEVE, and STRANGERS.

The 6th chip contained four files: BEACH, HOTTUB, SKYDIVE, and INTRUDER.

Several of these sounded dangerous, but some also sounded intriguing.

I decided to see what BEACH, BETH TOYS and HOTTUB were like. I booked time in the Holodeck later that night to 'preview' the programs before running them with Anessa.

I showered and laid down for a few hours of sleep. My alarm went off 4 hours later. I got up, dressed in some shop clothes (not my uniform), packed my weapon (a next gen phase pistol that shoots tachyon bursts, called a 'Burster'), and a spare communicator.

When I got to deck 15, I set up the Tricorder with the 6th chip first. I wanted to start with HOTTUB first. When the computer notified me that the program was ready, I drew my Burster and cautiously entered the Holodeck.

I was treated to an outdoor night scene. There was a hot tub in the centre of the room, encased in a cedar deck. The lighting was subtle and the full moon provided a really nice ambiance. There were crickets and birds chirping in the distance, and the temperature was in the mid 60s. A perfect night for a hot tub session.

While the simulated hot tub struck me as being both perfect for romance and relaxation, I still was wary, so I explored all around the deck, and the surrounding bushes. I even peeked under the deck to ensure there was nobody else in here with me. Only when I was satisfied that I was alone did I approach the water. Dipping my hand in, I found the temperature to be just right for my taste. I felt comfortable that I could safely show this program to Anessa, so I called out, "Computer, arch."

To my relief, the archway appeared right where it was supposed to. I gave the order to end the program and stepped out of the archway.

Next, I loaded up the BEACH program. This time when I entered, I stepped into the bright sunlight and a crowded beach. The beach stretched out towards the horizon in either direction. In front of me was a body of turquoise water (not sure if it was an ocean or a sea because I had no idea where this beach was). The beach was populated with people too: young, old, men, women, fat, thin, all different ethnicities. Everywhere I looked, people were lying on towels, or swimming, or playing volleyball. Needless to say, I was instantly anxious about being attacked again so I kept my Burster in my hand. However, the people on the beach didn't seem to notice me.

This might be alright to explore with Anessa at some point, but it was still a little unsettling to be amongst all those people given my experiences of a couple nights ago. Again I was relieved when the archway appeared when called.

Back in the hallway, I switched chips and initiated the final program of the night: BETH TOYS.

My gut clenched and my anxiety spiked as I entered another white non-descript room with no windows. However, instead of a single chair in the middle of the room, there were two bean bag chairs and a table. The table was littered with several dildos and vibrators of varying sizes, colours and shapes.

However, I didn't focus too much on the items in this room because it was the woman sitting in one of the bean bags that held my attention.

She was breath-taking. Tall, lithe and completely naked. She smiled as I entered, and spread her legs wide to display her shaved muff and moist labia.

"Annie, I was waiting for you. I'm so glad you came back. I was thinking about when we used to share a room in our house on Bronson, and how we used to masturbate for each other. It got me all horny, so I came here to Titan to do it again. What do you say Annie? Do you want to show me how you diddle yourself?"

I found my voice and said "Sure".

She looked at the table and pursed her lips. "Mmm which one should I select for myself? You choose Annie. You always had the best taste for what gets me off. Mom, daddy and Steve can't get me off like you do."

My prick began to swell as I considered what this gorgeous woman was saying. Annette must have had relations with this woman, who was most likely her sister. This woman obviously had incestuous relations with her parents and someone named Steve (a brother perhaps). It would stand to reason that if this nameless woman was carrying on those relations, that Annette also had sex with her parents and siblings.

Turning back to the task at hand, I selected a black dildo from the table and handed it to her. It was about 8 inches long, thick, and had an attachment that was meant for clitoral stimulation. She smiled as I handed it to her and purred, "Mmm I was hoping you'd pick that one Annie. Now get undressed while I pick out a toy for you to use."

I didn't know how she was going to react to my prick and the fact that I couldn't use her dildos, but I still stripped. I was so horny I was ready to burst.

When my fully erect cock sprang into view, the woman exclaimed, "Oh, you came equipped with a cock today Annie. That's ok by me. You know how much I love watching Daddy and Steve jerk off for us too. Do you want to start, or do you want me to begin?"

My voice cracked as I said, "You start."

"Ok Annie. I usually like to start by sucking my toys. You remember? Lick it like this." She demonstrated by taking the whole head into her mouth, swirling her tongue around and making all these sexy slurping noises.

I encouraged her to see how much she could take into her mouth. She removed the black rubber phallus long enough to say, "You know I can take the whole thing silly. It's smaller that Daddy and Steve." Then she proceeded to insert the dildo back into her mouth and I watched the head and most of the shaft disappear down her throat until the clit stimulator was digging in to her nose.

I began stroking myself as I watched this beautiful woman deepthroat her dildo. When she saw me start touching myself, she removed the giant dildo from her mouth and invited me to sit. I sat in the bean bag chair opposite her.

"Annie, do you remember when we first started masturbating for each other? I kept thinking about how hot it was that my little sister would lie in her bed right beside me, and play with her little pussy. So then I would start touching myself, and being loud about it because I hoped that you would hear me. It felt so naughty."

"And when I was in mom and dad's room with either Steve or Daddy, I know you always heard them fucking me because when I would come back to our room, your covers were thrown off. You always sleep with covers except when you masturbate. Remember the first time you actually just sat up and watched me? It made me cum so hard. And then you showed me how you do it and we both came together. Oh my god, I'm so wet just thinking about it. So today I wanted to show you how horny you make me Annie. And I wanted to watch you. And I always loved how you would tell me what to do to myself. What should I do to myself right now Annie?"

This was my cue. "I want to see you shove that big dildo up your cunt, then pull it out and suck it clean."

She complied with my request. She spread her legs wide, ran the head of the dildo up and down her slit a couple times, then plunged it in deep. She cried out in pleasure as it bottomed out and her clit took a beating from the stimulator attachment. After jamming it in and out of her cunt a few times, she slowly pulled it out and made a show of raising the glistening black cock to her lips. She moaned in pleasure as she licked the head, then engulfed the whole thing and began to fuck herself in the mouth.

I spat into my palm and began stoking myself in earnest. She removed the dildo from her mouth, slipped it back into her wet twat and watched me jerk off. As I began to stroke faster, she picked up the pace and began to plunge the dildo in and out faster as well.

"Annie, do you remember the first time I squirted for you? Do you remember how I shot my cum from my bed across to yours? And I was so loud that Daddy came in to investigate and ended up fucking me while you watched! That was so hot! I always think about that night when I need to cum. In fact, I think I'm going to cum soon."

"Me too," I grunted.

"I want to see you cum. Cum for me."

I watched as that dildo began pummeling her pussy at a furious pace. Her other hand cupped one of her nice conical tits and began tweaking the nipple.

As she began screaming through her own orgasm, mine erupted too. Thick ropes of hot jism shot from my cock, coating my crotch and belly.

Once my balls had emptied themselves, my stiffness began to soften. Her orgasm also began to subside and she pulled the huge dildo out of her cunt.

"Here, taste my cum Annie." She held the dildo out for me. I took it and touched my tongue to the head. It tasted wonderful - a little musky but very pleasant. I closed my eyes and took the entire head in my mouth and began to suck it just like I had done when I sucked my first cock.

I felt her hands on my lower abdomen near the base of my cock. I opened my eyes to see her scoop up some of my cum and place it into her mouth.

"Mmm yummy. You taste so good Annie. Not like you normally taste, but still great."

I got a little bolder and said, "Go on and clean it all up then."

She proceeded to lick and suck all of my jism from my belly. She took my deflated manhood into her mouth and cleaned my cock too. Then she came up and kissed me deeply. I moaned into her mouth as I tasted my cum on her lips.

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