My First Time, Truth or Dare

This is a story about something that happened in university. Well, not just something, but my first time...

I was 20 years old, and this was the third year. I was studying a BSc degree in Computer Science, and doing well. I'd never been with a girl, not even kissed a girl. It wasn't that I was unattractive, I was pretty average looking, average height, slim but not muscular build, short blonde hair, green eyes, glasses, but I was nerdy and very nervous around girls. If one looked at me, I'd turn red, and if one spoke to me, I had to make a quick exit. I kept my days busy with classes, studies, computer games, and regular solitary walks around campus. I'd also figured out how to bypass the network securities and spent many a time looking at porn in the computer labs and then jerking off in the lavatories.

But anyway, fast forward to the first holidays. Most people went home, but occasionally some folk would stay at the hostel through the holidays. In our building it was me and another guy. I needed to catch up on some extra credit assignments I was doing in C++, an attempt at a simple text adventure game. I also needed to tutor Jason, which is why he was staying there. He was also doing Computer Science but had failed two of his exams and needed my help to prepare for his rewrites. And since he was staying there for the holidays, his girlfriend Tanya, who was studying Sociology, was staying in as well. They had met on the first day in orientation and had been together ever since. He was taller than me, with dark hair, and very intense features, girls swooned around him. Tanya pretty much did anything he wanted, there were all sorts of rumours, but I won't go into that. She was extremely pretty, also 20 years old, slender, petite build, long dark hair, hazel eyes. I admit she had been the subject of many fantasies...

Of course the fact that I often imagined her nude, and on her knees in front of me, meant I was expecially nervous around her, and struggled to look her into the eyes, and the one time it was especially bad, because she was bored and had joined us for the tutoring lesson. While I was oblivious at the time, I realize now they both knew my discomfort, and she had been revelling at teasing me. While I was trying to explain computer architecture to Jason she was distracting us with various jokes and giggles and stories about what and who her friends were doing.

One evening we were sitting in the lounge debating what to watch on the telly, and Jason stuck in one of his movies. It started off as some weird story about students I forget, that then progresses to said students stripping each other down. I realized then he'd stuck in a porn film! And with me and Tanya in the same room! I was surprised. But I couldn't take my eyes away from the screen. Jason and Tanya were rolled up in a sleeping bag, and I'm not really sure what they got up to, because I was too embarrassed to look at them and I didn't want them to see how red I was, or that I was getting extremely turned on. After several scenes, I mumbled about needing to piss, and ran to the loo and quickly jerked off because my hardon had become really uncomfortable. I went back to the lounge trying to appear nonchalant, and Jason looks at me and says "Wow he must have been ready to pop to be done jerking off so quickly!" and Tanya giggled. My face turned completely red and I ran to my room and hid myself away for the rest of the evening. Of course the rooms were pretty close to each other, and in the quiet of there being so few people around, I could hear their moans and I knew they were fucking. I got hard again, and listened to them while I jerked my cock.

The next day I was eating breakfast in the lounge and watching cartoons, and Jason walked in and sat down. "I'm sorry about yesterday", he said, "I was just ribbing you."

"Its ok" I said, still feeling embarrassed, "I was just embarrassed with Tanya being there."

"Dude, all guys jerk off, its no secret. And Tanya's cool! Now if your parents were there, that would be something to get red about!"

I turned red.

"Andrew, seriously, when did you get laid last?"

"Ummm." I was getting uncomfortable with the conversation.

"When did you last go on a date?"

"Ummm." was my reply.

"Dude, have you never gone out with a girl?"

"Ahh... no." I whispered and stared into my cereal.

"Dude! Ok, I'm taking you under my wing, I'm gonna make sure you pop your cherry before the month is over!"

With that he left, and I continued staring into my cereal, with all sorts of thoughts coming to mind. I was so desperate even just to kiss a girl. To know what that felt like... I wondered what it would be like to kiss Tanya? Of course that led to thoughts about what it would be like to feel her mouth on my cock... my hand crept down and massaged my growing bulge through my pants. As soon as I was done eating, I went to my room, locked myself in, stripped down and lay down on my back, and jerked off into a kleenex while I imagined myself sucking on Tanya's pert breasts.

I figured Jason was just talking big, like folk always do when they say they'll do something and it never happens. And nothing did happen, for the next few weeks. Rewrites are always before the start of the next semester, so that they can find out before the semester starts, whether to accept admitance. Jason wrote his papers, and a couple days later he got his results, and he'd aced them! Tanya was there as well when he found up, and she'd jumped up onto him, with her legs wrapped around his waist, and they were kissing each other, and of course, I looked at them with a mixture of discomfort and jealousy and arousal.

Jason looked at me and said "Andrew, we're celebrating tonight, all of us! Tanya, because she's been great support to me, and you, because you helped me study for this."

"Uhh, ok." I replied, not really used to being invited to parties or such.

We met up later at the lounge, Jason had put out some blankets to make it warmer, as winter was coming. He'd stuck a cheesy horror flick on in the background and him and Tanya were cuddled up on the floor sitting with their backs to the couch. I sat on another chair to the side. There was a bottle of rum on the table, and Jason was smoking a joint. He offered me a puff, and I declined, it wasn't something I was really interested in.

"Well, at least take a drink!"

I looked at the bottle, and got myself a glass of coke and mixed in a shot of rum. I sipped it slowly.

Jason whispered to Tanya, and she gave a giggle, She looked at me then, and said "Andrew, why don't you get one of those boardgames you really like?"

I ran to my room and grabbed Munchkin, I always love playing that game. I quickly set it up.

"So how do you play?" asked Tanya.

"Umm, well..." turns out when it was about talking about stuff that I loved, it was a bit easier with girls... "umm, you go to get to level 10 here. And you do that by killing monsters or playing other cards. Each turn you get the top card of the door deck here, called kicking down the door, and you fight it if its a monster, and if you win, you get treasure. It sounds a bit complicated at first, but it gets easier when you play it."

We started playing, and we were having a really good time. Tanya spent a lot of time giggling at the various jokes in the game. Jason had played it before, and I knew he wasn't a big fan, but he seemed to be enjoying it since it was obvious Tanya was enjoying it.

At one point in the game, we were all stuck around level 3 because we were managing to really interfere with each other's turns, and the game was taking a bit longer than it should. It was Tanya's turn and while she was plotting her turn, Jason looked at me and asked "Andrew, Truth or Dare?"

"Umm, sorry?" I looked at Jason momentarily confused.

"Pick one, Truth or Dare?"

"Umm, Truth, I suppose..."

"Have you ever kissed a girl?"

I turned red, and started mumbling. Tanya looked up from her cards and said "Don't be shy Andrew, just answer truthfully."

"Umm, no, I haven't."

Tanya gave me a weird smile, and I could feel myself getting redder. "Well," she said, "I think I know what I'm going to do. I got that curse when I kicked down the door, so I can look for trouble with a monster from my hand. I'm going to try to fight this level 10 guy here, but I'm going to need help to defeat it. Andrew, if you help me, I won't give you any treasure, what I will give you is a kiss."

I coughed at that, and turned completely red. I probably looked like I was ready to run, and Jason put his hand on my shoulder to keep me from bolting, and whispered to me, "Seriously, go for it. Take a chance."

I told her I'd help her, and she defeated the monster and moved up a level. She then leaned over the table towards me with closed eyes and puckered lips. I looked at Jason, and he nodded. I leaned closer, my hands feeling clammy from nervousness, and my heart beating, and I kissed her on the lips, a quick peck, I was too shy to try anything else, and sat back down. She sat down too and gave me a smile, and that made me feel a bit better.

The game turn went to Jason, and he told me while he was busy I should ask Tanya a Truth or Dare question. I did, and she responded with "Truth."

"Umm..." I searched for a question to ask... "How many guys... umm..." I couldn't finish the question and looked down embarrassed.

"Just Jason here." she replied frankly. "He was my first."

"Ok, I got this Level 12 guy here when I kicked down the door." Jason interjected. "Tanya's playing to win and won't help me, and, frankly, I don't want a kiss from you." Jason joked, and Tanya giggled. "Oh, I know! Who's in favour of discarding clothes for like a +3 bonus?"

We'd been drinking while playing, and this was obviously making us all very suggestible. Tanya quickly responded with a "hell yeah!", and I mumbled an agreement. I knew where I wanted this game to go, and I remembered Jason's promise and wondered if he had orchestrated this, but the insecure part of me was also worried that I was just going to embarrass myself by doing something I shouldn't. But this was straight out of some of my fantasies, and I couldn't let the chance slip by.

"Well I need a +5 so I'm ditching these two shoes here." Jason quickly kicked off his shoes and reached for the treasure pile. The turn went to me and as I kicked down the door, Tanya asked Jason "Truth or Dare?"

Jason responded with dare, and Tanya dared him to take his pants off. "Oh, I see where this is going, you want to take away my advantages!" he laughed and quickly removed his pants too. Just before he sat down again I could tell he had a hardon with the way his boxers were tented. I decided to also get rid of my shoes for an advantage in my combat, and quickly moved up another level, the turn passed to Tanya, while Jason asked me the question.

"Dare" I responded, starting to feel a little braver, and enjoying the way I was feeling more comfortable around them, especially Tanya.

"Well I don't want to be the only guy without pants, so why don't you take yours off as well?"

And there I reddened again, ok, so I wasn't that comfortable yet. I pulled them off while trying to stay covered, I was definitely shy about letting either of them know how hard I had gotten.

Tanya was able to just beat the monster, and Jason stopped her. "Nah, too easy, dear, you're not getting off lightly." And he put down a +10 and another +5 monster enhancer.

"15 points!" Tanya exclaimed.

"Remove some items, or lost the fight..." Jason replied.

Tanya looked at me with a questioning look. I wanted to help her... but I wanted her to strip as well, she quickly realized what I was thinking and gave me a smile.

"I don't lose." she said as she quickly discarded her shoes and socks.

"Thats 12 points..." Jason quiped.

"I know." Tanya replied sticking her tongue out. She quickly pulled a blanket over herself, and after some maneuvering chucked her bra at Jason, grinning while she did so. "And I know you guys are ganging up on me now so you can see me naked!"

"Well Andrew here has now finally kissed a girl, I think its time he sees some boobs!" Jason quiped, and Tanya giggled, and I wondered how much redder my face could get.

"Dare, Andrew," Tanya said.

"Sorry?" I was lost for a moment.

"My choice, I choose dare."

"Umm..." I knew what I wanted to dare, but I was afraid to ask it.

"Dare her something, Andrew" Jason said, "Or you skip your chance... stop being shy."

I looked at Tanya, she was looking really sexy, and I knew her bra was off... "umm, your top."

"My top, what?" Tanya asked, but she asked it softly, like she was urging me to continue.

"Uhh, please take off your top." I managed with a bit of a stutter.

Tanya quickly pulled her top up over her head, and there they were, perfect pert breasts with small pointy nipples. "See, that wasn't so hard, Andrew."

"Uhuh"

"Andrew."

"Uh, yeah?"

"You can close your mouth now..."

I shut my mouth tightly, and forced myself to look away. I glanced at Jason, and he was grinning. I quickly realized he'd finished his turn while I was distracted, he'd removed his socks. I reached for the door deck.

I only had to discard my socks to beat the monster, I quickly did that. But then Tanya through down a +2 and I realized I'd have to get rid of my shirt to beat it. I wondered if I should run away, but Jason pointed out that the socks I'd removed would be a wasted bonus now, I couldn't take that back. I figured I'd go for it, and I removed my shirt.

"Wow, Andrew, you are white! Do you ever see any sun?" Jason commented.

"Hey." said Tanya, "I think its attractive."

I looked down at that, feeling embarrassed again. And as I looked down, I saw the tip of my cock looking back up at me, it had slipped out of the boxers. I quickly grabbed a pillow to cover it, hoping they hadn't noticed it. But they did realize something was up because of my action and smirked at me. Jason looked at Tanya, "I think our boy here is getting excited." Tanya grinned at that, and I wanted to hide my face in the pillow except for the part it was covering my embarrassment.

The turn moved on to Tanya, when she exclaimed, "Oy! I almost forgot! Truth or Dare, Jason?"

"Dare."

Tanya grinned, "remove your shirt, buster."

Jason quickly took it off and tossed it aside, showing his toned upper body. He leaned back, not really caring that his tenting boxers were very visible now.

"Truth or Dare, Andrew?"

I was feeling very vulnerable right them being almost naked, so I opted for Truth.

"When did you last masturbate thinking about Tanya here?"

I was taking a drink at that moment and spluttered.

Tanya looked at me, "Its ok, Andrew, you can tell us."

"Umm, this morning..."

"Aww!" responded Tanya, "Its a massive compliment to be the subject of somebody's fantasy."

Tanya did her turn, and was forced to discard her skirt to beat her monster. She was wearing these sexy polka dot panties. The turn moved to Jason, and I asked Tanya, and she responded with Truth.

"I'm not quite ready to lose my panties just yet, mister." she quipped.

"Umm.. have you...umm...ever given a blowjob?" I managed, and suddenly wished I hadn't asked.

Tanya giggled at that, "Andrew, you're so innocent. I love giving blowjobs, and Jason loves receiving them, I give him plenty of that."

I felt my cock wanting to burrow a hole in the pillow with that mental imagery.

Jason was just able to beat the monster he was fighting, but then Tanya added a modifier...

"It was bound to happen eventually!" he quipped, and stripped his boxers off. It was standing at full attention, at about 7 inches. My mind boggled at how this evening was going, and how it had suddenly taken a serious step forward that I wasn't sure how to react to. Except for porn, I'd never been in the presence of another nude person, always shying away from public showers and even pools, not being comfortable with my own body. Jason sat down, "Your turn buddy."

I couldn't stop thinking about what might happen with the way things were going. Would I see Tanya completely naked? I glanced at her tits and wished I could touch them. Tanya felt my gaze on her and winked at me. My cock was getting really uncomfortable. I wanted to run off and jerk it off and then hide away for the rest of the evening. But I didn't dare to, my shyness was being overriden by the application of coke and rum, and the desperate need to get lucky and do really stupid things to achieve that. I looked down at the door card I had drewn. I needed +3 to beat it... I looked at Jason and at his cock on display. I wondered if I could be so brave. I looked at Tanya, she nodded at me, urging me on. I took a deep swallow from my drink and stood up, and pulled down my boxers. My 6 inch cock bounced up, as the waist strap passed below it. It was uncut, but the foreskin was pulled completely back revealing the purple angry-looking tip. Both Jason and Tanya gave wolf whistles, and Tanya licked her lips. My shyness suddenly reasserted itself and I smacked my hands infront of my groin, a bit hard, causing me to groan from a sudden pain, and I sat down, and pulled the pillow over me again.

"You're gorgeous, Andrew, I have a few friends that might be interested in taking that for a test drive..." Tanya said, I couldn't reply. "Oh, almost forgot again, Jason, Truth or Dare?"

"Truth."

"What did you tell me this morning?"

"Hehe," Jason gave a small laugh, "I told you I'd promised I'd find a way to get Andrew's cherry popped."

My ears got all hot and ringy with that, I looked up from Jason to Tanya. And Tanya nodded at me, gave a wink, and licked her lips again. My face burned, and I could feel the underside of the pillow getting gooey as I was leaving a trail of precum.

"Truth or Dare, Andrew?"

"Umm... dare." I said softly.

"I dare you to remove that pillow, don't be afraid to show what you've got."

I slowly moved the pillow away, and I couldn't bring myself to look up immediately, but when I did I saw Tanya's gaze going down to my cock.

Tanya did her turn, and again, she needed some help with the monster. "Well all I have left is my panties, but that doesn't cover what I need to beat it. Would a kind, helpful, stranger help a damsel in distress for a favour?"

Jason remained quiet, and I was quiet too until I realized they were waiting for me. I looked at them, "Umm, I'll help, umm... for..."

"Ask for anything in return, Andrew..." Tanya said, "Anything at all."

"umm, I want to... umm... I want to suck on your nipples."

"Ooh, deal!" She grabbed her treasure and level and then looked at me. "Now how should we do this, ooh, I know, stay put!"

"Umm" was all I could respond with. Tanya quickly moved around the table, and came to stand right in front of my, her panties at level with my face, I stared at her crotch wondering if I could make out details through the cloth. She started moving down, kneeling over my lap, and then she sat down, pressing her groin onto my cock.

"Ahh!" I exclaimed, the physical contact of my cock with another person being a massive stimulation I'd never experienced.

"Shh" Tanya said, "Relax, and enjoy it."

She slowly ground herself against my cock and she reached her hands behind my head. I looked to Jason, and he was only grinning. She pulled my head forward against her chest. I gave a kiss to her skin, and then stuck my tongue out and gave a quick lick, tasting her skin and her sweat, it was enticing. I reached up and cupped her breast in my hand and massaged it, and then I leaned in and sucked her nipple into my mouth and started suckling on it. She started moaning, grinding faster, and I started moaning too, alternating between sucking and biting on her nipple.