Holodeck Discoveries Ch. 03

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Guy discovers kinky sex fun on the Holodeck.
4.8k words
4.32
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6

Part 3 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 63233.6

I am in the process of describing the events that have happened since I boarded star base 12 almost 6 months ago. In the last log, I explained how I had reconciled with the sexy Anessa Gordon, how I determined the contents of the other six memory chips and did some exploring in three of Annette's Holodeck programs, and finally I described my amazing encounter with Annette's sister. Even now, my cock is hard just thinking about it.

I am amazed at the sexual liberation I have undergone. I used to be so repressed. However, experiencing a stranger's sexual fantasies awakened desires in me that I didn't even know existed. I now look at the world differently.

So the morning after my experience with Beth on the Holodeck, I got ready for work and made my way down to the hangar.

******

Anessa was waiting for me with coffee and an expression of barely-contained excitement.

"Tim I was doing some research last night on Annette Fellowes and I found out some really interesting things."

I chided her, "Good morning to you too Ensign. And thank you for the coffee."

"Oh, you're welcome," she responded distractedly. "Do you want to hear what I found out?"

"Sure. What did you learn about Annette?"

"Ok, so she is the youngest of three. Raised in Cleveland. She didn't do very well in school and failed her Starfleet entrance exam 4 times before she gave up and stopped trying. But her older brother Steve went on to become a captain, commanding the Melbourne F. Her older sister Beth was the chief medical officer at star base 14. They both had excellent long careers with Starfleet. Her parents were also Starfleet: her father Carter achieved the rank of Lieutenant and served as security officer aboard many ships before returning to Earth to raise a family. Her mother was an botanist serving aboard various far-flung star bases. "

"Annette got arrested on Earth in her teens for vandalism of Starfleet property, then she was arrested on the moon for assault against a Starfleet Admiral and his aide (although the record didn't mention the name of the aide nor the Admiral), and finally two arrests on Titan for assault and forced confinement of her superior. After getting out of the penal colony on Nelvar 3, she went to Deep Space 9. There, she apparently joined a Cardassian cult and, although it was never proven in court, she was part of several attacks against Bajorans. She was killed in a bomb blast on DS9 that killed 8 other people. The bomb was apparently set by her 'cult'. The records are vague as to what she was doing in the vicinity of a bomb set by her own group. All in all, it seems like she was pretty troubled, and had a real problem with Bajorans, authority and Starfleet."

"Wow, thanks for that summary Ensign. Now today I thought we would attempt to balance the antimatter flows in the injectors and clear that obstruction in tube 7B."

Her expression changed from one of excitement to one of disappointment. "Oh, ok sir. It's just that..."

"That what Ensign?"

She sighed and said, "I was really hoping to go check out some of her Holodeck simulations today. Maybe we could spend the day exploring what made this woman tick."

I was frankly a little surprised by her desire to delve into Annette's Holodeck simulations. Why was she so anxious to see what was on those chips?

"Why is that Ensign? We have more than enough work to keep us occupied, and I'm worried about falling behind schedule. Don't forget that we have a shipment of inverters arriving tomorrow and so we need to get that obstruction cleared."

She still looked disappointed. She signed again and said, "I know sir. It's just that we've been working so hard on this project, and I feel like I need a bit of time to unwind. Usually I go to the Holodeck to do that, but I haven't had time to write any of my own programs yet. I forgot to bring my own stored programs from my last assignment, so I haven't been able to really experience the Holodeck here yet."

Feeling magnanimous, I replied, "I'll tell you what Anessa. Let's get our work done today before lunch, and I'll give you the rest of the day to program some new Holodeck sims for yourself. When we get ahead of the curve, we can explore some of Annette's fantasies...er, I mean, programs together." Oops, I hope she didn't notice my turn of phrase there. I peered at her, trying to see if she caught what I said about fantasies, but I didn't detect any change. If anything, my offer didn't appear to make her much happier. Her body language and expression gave me the impression that she had resigned herself to being disappointed in the short term. She said, "Ok sir" and walked away.

Suddenly I felt guilty about having experienced two of Annette's Holodeck programs, when it was evident that Anessa also really needed to unwind on the Holodeck, but had not had a chance to do so yet. I was really hoping to reach the next milestone in our project so that she could enjoy some down time. And I was also looking forward to showing her some of the tamer programs like the Hot Tub and Beach. But I wanted to protect her from anything inappropriate.

I would continue to keep the ones featuring Annette's family to myself though, because like Anessa, I needed some downtime too. Besides, they were a great way to relieve my tension.

Speaking of tension relief, I was already looking forward to another encounter that night. I had resolved to try the program called BETHSTEVE because it sounded kinky.

The work towards the next milestone progressed and we finally got the obstruction cleared in 7B, and was able to balance the anitmatter flows (even though we had to work through our normal lunch break to do it). I allowed Anessa to leave 4 hours earlier than normal, and admonished her to try to write some new Holodeck programs for herself. I finished up and left the hangar for my own quarters.

After a shower, I went to call on my sister. Becky was cleaning up after lunch, and my nieces were sitting on the floor doing some colouring. She fixed me a sandwich and we sat down to chat about the project and life in general. After a while, she rounded up the girls and sent them off to their dance lesson in the Holodeck.

Then she sat back down and proceeded to pump me for information. She asked if I was seeing anyone yet, and I said no. She asked if I was interested in anyone. When my answer was a bit delayed, she sensed that I did indeed like someone.

"Who?"

"I don't want to say," I replied.

"Does she know?"

"I think she does, but I don't think she feels the same way."

"Is it Anessa? She is so pretty."

When I didn't answer, she exclaimed, "I knew it! Oh Tim, she's perfect for you. You both have so much in common and, if I remember growing up, she's your type too. Remember Rosie Templeton? Anessa reminds me of Rosie."

Ahh, Rosie Templeton. My first serious girlfriend. She was the only black girl in my class, and all the boys wanted her because she was exotic and her tits were spectacular. We went steady for 2 years, and I gave her my virginity. Our relationship ended after I caught her fucking Becky's boyfriend at the time (some douche named Trey).

"Shut up Becky! God! Don't remind me of Rosie. And besides, I can't really date Anessa since she is my junior officer. Starfleet frowns on that sort of thing."

"But Tim, Paul dated and married me."

Like I said, she wasn't the most aligned phase coil in the engine. I said, "Yes, but you were never in Starfleet, nor did you ever report to Paul as your superior. You were working at a coffee shop when you met, remember?"

"Oh, I guess you're right Timmy. Anyways, Anessa reminds me of Rosie. Not in the bad way, you know with Trey. But like the colour of her skin and her boobs. Oh my god, she has great boobs."

I laughed nervously and said I hadn't noticed.

My big sister looked me in the eye for a moment, her cheeks flushed. Then she looked away and said in a softer, less exuberant tone, "You know Tim, Trey was my first. And he was so great. I was reluctant to have sex with him at first, but he kept after me. And my first time it was amazing. After that first time, we uhh, got together whenever we had a chance. And when we caught him and Rosie together, the way he was...uhh..with her was a revelation. Remember how we stood there watching them for like 5 minutes before we finally said anything?"

This was probably the worst memory from my adolescence. We had been away from home for a week visiting relatives in Maryland. We returned a day early and had gone to our usual hangout spot to see if anyone was around. Imagine our surprise to find our mates enjoying an energetic fuck in our absence. I loved Rosie so much, but she destroyed my trust.

"Yeah Becky. listen thanks for this painful trip down memory lane and the lunch, but I gotta get going." I stood up and turned to walk out.

"Wait Timmy, I'm not done yet. Sit down."

I was surprised at the tone of command in her voice. And equally surprised that I complied and sat down again.

She continued, "Timmy, there's something I need to tell you. Remember how we caught them and you went in and yelled at Rosie and called her all those awful names and broke up with her? Well, do you remember that I didn't say anything to Trey?"

"Yeah, I just thought you were too shocked to speak."

"Well I was shocked, but to be honest, I was also turned on watching them. I called Trey the next day and we arranged to get together with Rosie." Noticing the anger rising in my face, she said, "Don't hate me Tim. I had always fantasized about being a part of something like that."

My emotions were a jumble. I felt angry, regretful, betrayed, and a little curious. I suppose everyone has fantasies, but my own sister thinking about watching other people fuck, and potentially joining them was new information that reset my opinion of her. For the longest time, I had always seen her as a "mom" type because she was four years older. She had a big role in raising me after mom died when I was 12. It's kind of hard picturing your mom or big sister as a sexual creature with kinks and passions of her own.

Still, at this moment, the anger, regret and betrayal were forefront in my mind. "How could you Becky? You know how bad Rosie destroyed me! I loved her and she fucked Trey behind my back. And now you're telling me you joined them too? After you knew how upset and heartbroken I was?"

Quietly "Yes."

I lashed out, "Fuck you Becky!" I got up and stormed out of their quarters.

*****

So there I was back in my quarters, reflecting on disappointment. I had disappointed Anessa. My big sister had disappointed me. I grabbed a bottle of 34 year old Talarian whiskey and poured myself a stiff one. Captain Tii'vad had given it to me as a gift as I departed the Outlook. At least Captain Tii'vad had never disappointed me, nor had she ever expressed any disappointment in my performance (although I was still unsure if Vulcans could express disappointment).

Before pouring my second glass, I booked my time on the Holodeck for 3am and set my alarm. Good thing I did too, because I proceeded to get royally drunk and ended up passing out whilst consuming my third glass.

*****

Still slightly drunk, I awoke and had another small glass of whiskey. Although, I will say that I at least put some water in this one. I left my quarters with most of the equipment to run another Annette program on the Holodeck. Once I got up to deck 15, I realized I had forgotten the latinum cable in my quarters. So I had to go back and get it, then return to the Holodeck.

It took some muddling, but eventually I got the BETHSTEVE program loaded and entered the Holodeck when instructed.

Once again, I stepped into a white room with no windows. There was a table containing a variety of dildos, a beanbag chair and a regular chair in the centre of the room. Surprisingly though, there was nobody in the room with me. I rubbed my eyes and looked around. Still empty!

I called out for Beth. No answer. I called for Steve. No answer.

I called out for the arch. The archway appeared and I stepped through it. But instead of stepping out onto the deck, I found myself in a darkened bedroom! It looked like a girl's bedroom. I turned around to exit, but the archway had disappeared. This was getting weird.

I looked around again at the room in which I was standing. The bedroom contained two twin beds, two dressers, a big mirror and a large closet. But it definitely appeared as though two very different people occupied the room. One side was very 'girly' featuring posters of effeminate looking boys and cats and horses. That bed was littered with stuffed animals. The other side of the room featured a posted of a very angry looking bunch called Guns N Roses, a sculpture of a skull with a snake emerging from the eye socket and some sort of glass enclosure that housed a very large spider.

I turned on a lamp that was close to me, and inspected the dressers. I picked up and examined some of the various items scattered around the room. I went and observed that large spider for a moment, but it was just kind of sitting there, not moving. I approached the closet and looked inside. It was indeed pretty large. I could see a string hanging from the ceiling, so I reached for it and clicked on the light. Other than being full of clothes, there was nothing of interest in there. As I was backing out of the closet, a pair of soft hands closed over my eyes and a soft body pressed against me.

"Shhh, Annie, guess who?"

"Beth?"

"Yes, how did you know?" She removed her hands from my eyes and I turned to face her. This was a younger version of the sexy woman with whom I masturbated the last time. I would peg her age at about 18, 19. Unlike our masturbation encounter in the white room, this Beth was 'clothed'. Still, she was definitely sexy. Her hair was done up in a pony tail on top of her head. She was wearing a cropped shirt that exposed her flat tummy, and her hard little nipples were poking out. On the bottom half, she was sporting a pair of panties that hugged her hips, revealing her curves and toned buttocks and smooth skin. She was the complete picture of youthful sex appeal, and I could see the beginnings of the sultry seductress that she would grow into.

I laughed and said, "Lucky guess."

"I came home while you were out at work."

"Came home from where Beth?"

"Oh Annie, you silly thing. I was away at college, remember? And call me Bethy, just like you used to."

I said, "Ok Bethy. Sorry, I forgot you were away at school."

"And you'll never believe what happened when I came in the door?!? Mom and Daddy were waiting for me naked! I just got finished fucking them about 15 minutes before you got in the door. Daddy's cum is still inside me because I haven't had a chance to shower yet. I wanted to wait for you, and was hoping you could join me in the shower."

My prick had become rock hard at this point. I pulled Beth towards me and kissed her deeply. She just melted into my arms and accepted my kiss. Our tongues entwined and our kiss deepened. My hands moved down to her little pear-shaped bottom and I squeezed her and pulled her close to me.

Beth pulled back from the kiss and asked, "What is that poking me through your pants Annie?"

I was now getting more used to the idea that Annette's Holodeck characters were expecting a woman, but would just roll with whoever came along, so I decided to roll with it too. "It's my cock Beth. I'm going to fuck you with it in the shower."

"Mmmm two cocks in my pussy in one day? I must be lucky."

A male voice from the doorway said "Make that 3 cocks Bethy. I want to get a piece too."

I turned towards our new guest and determined that this must be Steve. He appeared to be in his mid-twenties, short and handsome. He was naked from the waist up, toned without being too muscular. He was wearing shorts, but the bulge in the front of them drew my attention. He said, "Don't stop on my account girls."

Beth turned to face me again and renewed her sexy kissing. Steve approached us and positioned himself on the other side of Beth so that she was sandwiched between us. Beth moaned into my mouth as she was pressed against my chest. I felt one of Steve's hands come up to squeeze a conical breast and her pelvis ground against my now raging erection.

Beth stopped kissing me and turned her attention to Steve. As she kissed him deeply, I ground my own erection into her backside and reached up to cup one of her impressive titties from the back. Steve's hand joined mine and together we squeezed and kneaded her breasts, causing her to moan and gyrate her hips provocatively.

Then Steve's had was on mine and he pulled it lower and suddenly I was rubbing the bulge in his shorts. He removed his hand from mine and went back to Beth's tits. I pressed my hand against the fabric containing his rigid member, and he bucked his hips slightly, trying to urge me to touch harder. I curled my fingers around the shaft and stroked up and down a bit before teasing the underside of his cock head.

Never in my wildest dreams would I have imagined that I would be touching another man's cock through his pants, but here I was doing it, and I really enjoyed it too. Beth turned to face me again and told me to get undressed so we could get into the shower. I stepped back and quickly doffed my clothes and noticed that Beth and Steve were also getting naked.

Beth looked fantastic! Her skin was mostly a dark caramel colour, but with tan lines around where a two-piece bikini would be. Her nipples were hard and her fantastic conical tits stood up firm and jiggled a little with her movements. Her hips flared nicely and her long shapely legs appeared smooth and flawless. Her pussy was covered by a dense bush of brown pubic hair. Steve had revealed a thick 6 inch circumcised cock that proudly stood out from his dense patch of brown pubic hair.

I got undressed and followed them out of the room, down the hallway to the bathroom. Beth started the water running while Steve arranged the towels. I stepped in to the shower stall, and was joined by Beth, then Steve. We all took turns getting wet by the overhead nozzle, all the while with plenty of touching and teasing. At one point I worked my hand down between Beth's legs, down past her impressive bush, and splayed my fingers across her centre. As I dipped a finger into her wetness, I did indeed notice a lot of moisture that had nothing to do with the shower.

I spread Beth's labia with my first and third fingers, then focused on diddling her love button by flicking my middle finger up and down. She moaned and pushed her slippery tits against me. Meanwhile Steve had been washing himself, and now that he was rinsed, he approached us. His hand joined mine on Beth's cunny and he inserted his first two fingers inside her damp cavern. As he pumped the fingers in and out, I continued my assault on her clitoris, flicking it back and forth and rubbing circles around the hard little bud.

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