Truth or Dare

Typing out my story had left me fidgeting with excitement. I could feel the heat between my legs and my nipples hardening. Half of me wanted to touch myself, but I was embarrassed at exposing myself to Matt in this way.

His sardonic reply took the edge off my mood, but what had I expected him to say? It was my fantasy, not his. I desperately wanted to continue the conversation though and sent, "Your turn again now. This time you can choose properly. Truth or Dare?"

"You still want to hear my stories that go beyond the bedroom?"

"Definitely!"

"Then Dare."

"Bastard!" and, "Fine then. Dare it is"

I paused. Matt was playing along but, like me, he was probably just distracting himself. He had been dumped only an hour or two ago. He probably wasn't experiencing the same little sensations that flickered through my body every time I glanced at earlier messages or thought about what we had said. I decided to follow-up my request from after his last dare.

"OK. Another selfie. With as much of the 'various other stuff' you mentioned as you like."

"I could just send the same one if it's 'as much as I like.'"

"OK then. With as much of that stuff as you think I'd like."

My smile to myself was involuntary. Matt wouldn't know what to send. He was a sweetheart and his shyness could be all-encompassing. Some guys would send a dick-pic. I knew Matt wouldn't go anywhere near that far. He would probably send a picture of his tensed bicep or maybe a carefully cropped close-up of his six-pack, if he had one. Mulling over the options was entertaining me though. I noticed I was biting my lip and lightly stroking the bare skin above my vest top. I was also rubbing my bare feet against each other; a sure sign that my mind was in fantasy mode.

Memories of the walk in the park were competing with new thoughts about exactly what Matt looked like right now. He had been quite attractive as a teenager; a little skinny, but tall and sweet-faced with blonde-brown hair and blue eyes. I had rarely seen him wearing less than a t-shirt and shorts but, when we went to the beach and occasionally when I stayed over at his parents', I discovered that his tennis kept his slim body toned.

Impatient and keen to stop Matt thinking too much, I lifted my hand from my chest and sent, "I'm waiting," with a smiley face.

Seconds later, my heart skipped a little as Matt's picture arrived. As I opened it, I squeezed my legs together. My hand returned to my chest, but lower this time, over my breast, lightly pinching my nipple between two fingers, through my vest top.

Matt

By the time Jess asked for a second selfie, I had reread her story twice and each time left me more turned on. I don't know why I said dare. I think I still thought she would eventually back off and tone down the conversation. I hoped that a dare would limit her options for doing so and allow us to keep going.

Her request was frustratingly ambiguous though. I knew she definitely wanted to see the results of two years in the gym, but I had no idea what exactly she was after and how much she wanted to see. A big part of me assumed that she would be happy with a shot of my arm muscles, but to do that properly I would have to get out of bed. Other smaller parts of me, the parts that were still imagining coming across her in a park, with her hand beneath her summer dress, those parts of me wanted to send something more.

I pulled back the covers and held my phone above my torso, tensing my stomach muscles and shoulders. The result wasn't bad as the gym had toned me up and the shadows in the half-light accentuated that. The only problem was that I had allowed the top of my boxers into the picture and, although I had put everything away before taking the photo, you could see the bulge in the fabric without looking too closely. I had just started to crop the picture when a message arrived from Jess telling me to hurry up. Taking a deep breath, I cancelled the crop and pressed send.

For the first time, Jess was slow to respond. My stomach tightened as I realised I might have gone too far. After all, while I had been jerking off, Jess had just told me a funny story and sent a couple of vaguely flirty messages, which was nothing out of the ordinary for her. I flicked back over those messages, looking for reassurance that I had interpreted things correctly, but there was nothing definitive. I checked how long it had been since I sent my message and saw that it was four minutes. I started to type out something to prompt a response but kept deleting it after two or three words. Just as I was about to send an unimaginative, "You there?" she replied, "Aren't you going to ask me?"

"Ask you what?"

"Truth or Dare."

Jessica

My first reaction was to Matt's abs. Pronounced, defined and exposed. His chest and arms were impressive too. My hand slid back under the quilt and gently traced the outline of my nipple before caressing my breast through my top, letting my thumbnail trail over the bare skin above it. Then I noticed that Matt's black boxer shorts were in shot.

A little ashamed of myself, I zoomed in to see what was visible. Then I realised. My hand moved down my body and I trapped it between my legs, pressing down and sending a shot of arousal racing through my body. I could feel the heat there increasing and I drew my hand away, sliding it back up my body and underneath my shirt to massage my breasts, dragging my palm over the nipple.

I was still trying to resist simply touching myself. Through all my teenage mistakes, Matt been a symbol as much as a friend. The sweet guy on the edge of our group. Nobody's closest friend, but the one you could rely on. Even years later, I struggled against corrupting that.

I zoomed out again, looking at the whole picture. I flicked back to the first image. My imagination slipped again as I pictured Matt in the park. I saw myself taking his cock from his boxers and letting it part me. Then, changing, I imagined him walking towards me as I knelt, touching myself, even as I was still sliding him inside me. I saw the Matt that was walking towards me open his jeans and stand in front of me, within touching distance, stroking his cock inches from my face as I moaned in fulfilment while the other Matt, laid beneath me, slid himself deep inside. Again, I pressed my hand between my legs, arching my back to push against it.

Matt was typing a message. I hadn't replied. I wasn't sure what to say. There was no chance of telling him what I actually thought. I pressed on with the game and said, "Dare."

He came back quickly with a hint of revenge. There was also a hint of uncertainty. Something had turned him on and he wasn't sure where we stood. He claimed he hadn't seen me in ages and wanted me to show him as much as I thought he would like to see.

To be clear, Matt had only ever seen me clothed. We had never even swum or sunbathed together. Beach trips to the Yorkshire Coast are somewhat less sun-kissed than on the California shore and we usually wore t-shirts in the chilly North Sea. Similarly, when staying over at his house, we would both change while the other was in the bathroom. By the time he came back, I was always in bed and by the time I woke up in the morning, he would be downstairs eating breakfast.

I had to respond quickly. I couldn't keep Mat waiting again in case he got bored and fell asleep. I made a quick decision. I slipped my vest-top straps off my shoulders. Then I adjusted it so only the lace trim covered my nipples. Taking the photo quickly, I cropped it to leave him guessing and pressed send before I could back out.

It was my turn to wait now. At least I had Matt's pictures for company. I was struggling to stay calm though. I slipped my arms out of the straps entirely and pushed the pyjama top down to my waist. I returned briefly to playing with my breasts, but it wasn't enough. My hand sunk downwards and inside my bottoms, dragging over my underwear. It gripped the inside of my thigh, trailing my thumb around the edge of my panties, to the side of my pussy and then I dragged my middle finger up from my bum to meet it. Moving my hand to the side, I pressed down over my clit, my breath catching sharply. I could feel the wetness that had built-up since telling Matt about the park. I pressed down again, starting to rub slowly, short sharp breaths escaping as I pictured myself easing down Matt's boxers while he was texting me, revealing for myself what hid underneath.

Matt

My cock was out of my boxers again and I was rubbing it quickly, my hand moving up and down the shaft. If Jess had been ambiguous before, there was little to be unsure about in her photo.

Her face looked beautiful, slightly shy, bottom lip between her teeth, eyes looking straight at the camera. Her breasts were almost bare and large enough to be still well-defined as she lay on her back. All that covered them was a strip of white lace through which I could see glimpses of her nipples and the darker skin of her areolae. It looked like she had deliberately cut the photo off to leave me guessing as to whether the lace was part of her clothing or a thin slither providing the slightest avoidance of nudity.

Anxious not to leave her as long as she left me, I replied after a minute or two.

"Jess, that's really hot."

"Thanks."

"Seriously."

"Haha. I know. Well, I don't know it's hot. But I know it's flirty. Whatever. You know what I mean."

"Haha. Yeah, don't worry, it's hot"

"Your one was too. You inspired me. I'd love to see if everything still looks the same now."

"You'll have to wait and see if I pick Dare."

"Still playing are we?"

"I guess so."

"OK. Truth or Dare?"

"Truth?"

"Cheat! You knew what the dare would be!"

"Hey, I haven't done a truth yet!"

"Fine. Give me a minute."

While Jess chose her question, I flicked back to her picture but she came back almost as soon as it had loaded.

"Tell me what you were doing before I sent this message."

I froze. Then relaxed.

"Nothing. I was just about to go back to your picture but then you asked your question."

"Rubbish answer. Tell me what you would have been doing if I had waited longer."

"You don't get two questions!"

"I do when you dodge your dares."

"OK. OK."

I paused, unsure how direct to be, how to word it, whether to try and make it appealingly detailed, be crude and blunt, or whether to be coy. I started typing.

"I was going back to your picture. I was imagining the rest of the image, below where the photo cuts out. It reminded me of that game of strip poker at Heather's house, when her parents nearly caught us. You didn't lose a hand but you had taken off your shoes earlier in the evening. I'd realised that, if you did lose, your dress would have to go. That was the only reason I kept playing when I was losing.

"Just now, I was thinking that this is what I would have seen then if the cards had played differently. I was also remembering the taxi ride afterwards, when you were trying to get me to talk about Heather's underwear or something. All I could think about was how you would have looked underneath your dress."

I pressed send and then I realised it was stupid. It was just saying meaningless stuff to avoid saying what I was actually going to do before Jess texted.

Jessica

Matt's answer was not what I expected, but it did send a sharp thrill through me. He had only seemed interested in Heather and Ellie that night. That he remembered my role surprised me. That he had fantasised about me in the taxi and hadn't just been embarrassed about finding Heather and Ellie sexy -- that caused me to pull aside my underwear and touch myself directly for the first time. I moved up and down over my nub with two fingers, shivers rolling through my body. My phone interrupted me again.

Matt said, "Sorry, that was a weird digression. While looking at your picture, I was letting my hand wander a little."

"Be more specific."

"My hand was on my cock, rubbing it slowly, trying not to go too fast."

My breath caught and I released my underwear and moved my hand inside them, immediately slipping two fingers between my lips and feeling the heat inside. I drew them out, dragging the moisture over my clit, starting to move in circles around it, parting my legs further as I dipped back inside myself, drawing my fingers in and out slowly. With my other hand, typing unsteadily, I pressed deep inside as I replied "Really? Matt, that's so good to know."

"Yeah? I assumed you were going to go back to asking about sex outside my bedroom."

"Haha. I'd forgotten about that."

"Never mind. Truth or Dare?"

Matt was definitely embarrassed. He was trying to move things on. This was still weird and uncomfortable for him. For me too. But my fingers were back on my clit and flickering quickly across it now, my back arching as my breath came in short and unsteady bursts.

I spread my legs wider, lifting my knees and resting my feet on the bed as I kicked the covers off my body. I was fully exposed, my hand inside my underwear and my vest top around my waist. Frustrated that I couldn't text and touch myself at the same time, I rubbed furiously across my clit, lifting my bum to meet push against my fingers and gripping my breasts in the other hand, before flopping back onto the bed. Picking up my phone, I replied, "Truth."

"I liked your last story. Have you done anything else that risky? Sex-wise I mean."

That evening with Sean was my only outdoor experience. I'm more confident than Matt, but I'm not extroverted or a thrill-seeker. There was one thing though. It made no sense at the time. An expression of something I hadn't yet understood.

"Erm, this is going to be weird."

"OK..."

"Do you remember when I stayed over at your house after Jack's 18^th?"

"Yes..."

"After you fell asleep, I couldn't drop off. I was too wired and a little drunk. I kept tossing and turning. God, this is embarrassing but I often fall straight to sleep after an orgasm. So I started to touch myself. I had never done it with someone else in the room before. It was kind of sexy, knowing you were there, just a few feet away, but didn't know what I was doing.

"I went pretty quickly, just touching my clit, not going inside, but the covers kept rustling. I tried different positions -- on my front, my side, knees raised, legs flat on the bed, but everything seemed to keep making a noise. I was afraid of waking you up. So I pulled the covers away entirely and just lay on your sheets in my nightie, which I guess you never saw but it was green and satiny and, most importantly for this story, it was short.

"I had pulled down my underwear so everything was on display below the waist. You were right by the bed but you didn't stir. I could only rub my clit because going in and out was still too noisy, I was that turned on. But I did put two fingers inside and kept them there, moving them slowly around while rubbing my clit. It only took a few minutes longer but I came so hard that I had to bury my face in your pillow to stop from waking you.

"Sorry. That probably freaks you out knowing I was masturbating in your bed."

Matt

The pace of my hand increased rapidly, fingers running over the edge of my glans. I had no idea that Jess had got herself off so close to me, nor that I could have opened my eyes and seen everything. She was flirty and excitable, but never wild. She had had never come across in this way before. I replied with less caution now.

"Fuck Jess. That is so sexy and I never knew. I'm stroking myself even faster now and I'm close to coming."

"One more Truth or Dare?"

I backed out.

"Truth."

A brief pause and then, "Tell me what to do to myself. I want to cum"

Jessica

I swore audibly when Matt said truth. I also understood. This was new and he was still Matt. There was only one thing I could ask for if he said dare. This was the next best thing.

His messages came in in clusters, full of typos. I was picturing what he was doing while typing, part of me wishing I was sat naked astride his lap, so I could have my hands on him and his hands on me. Instead, I followed his instructions. I lifted my butt off the bed, pushed down my underwear and kicked it off my feet. I was naked now except for the vest-top, bunched around my waist. I was tempted to send Matt a picture of me like that as a bonus but that would mean removing my hand from between my legs. Instead, I spread thighs wide, as he asked.

Two fingers slid between my lips, sinking deep inside me. I began moving them in and out rapidly, drawing wetness from inside me and spreading it around my clit, alternating between rubbing with my thumb and driving my fingers back and forth. I was almost panting now as I read Matt's instructions.

Pulling my fingers out of my pussy, I moved them up to my clit, rubbing it hard and fast. The whole surrounding area was sensitised and sent arcs of euphoria from my centre, down my legs and through my torso. My bum was lifting off the bed as it rose to meet my fingers. My hips thrusting forward as I brought myself closer and closer. Short, high-pitched gasps escaped in quick succession followed, in a sudden rush, by a long low moan as a torrent of pleasure swept across my body. My legs clenched together, pinning my hand against me. Then, as I relaxed, I slowly started to move my fingers over my lips, between them and dipping gently inside. Bringing myself down from the intense orgasm.

I had told Matt I was close. His instructions had finished with him saying he was about to cum too. Afterwards, conversation became awkward. We were both a little shy and tiredness hit. We agreed to text in the morning and left it after a few more messages. I fell asleep quickly, less worried about my future and burning with fantasy.

------

Jessica

I woke up late the next day. Memories of the night before flowed into my mind and, as my phone vibrated on the bedside table, they crystallised into the image of Matt, naked and hard, telling me what to do to myself as he watched from the foot of my bed. The picture faded though when I saw the message. It was from my dad. He wanted to know whether I had come up with a plan. I sent back a vague reply saying I was still working on it and would call later. Then I lifted myself from the bed and shuffled to the bathroom.

By the time I sat in the hotel's restaurant, with cheap toast and weak coffee, my uncertain future had crowded my thoughts again. I texted Matt before I got into the shower but he hadn't replied. That, in combination with my surroundings, wilted all fantasy.

Across the restaurant, a couple with a toddler were trying to feed him some bacon. A woman in a business suit, only slightly older than me, jabbed at her phone while chewing a bagel. At the table to my left, a waitress was clearing dirty plates left behind by a stag party. Her faded brown hair and rough skin offset by a friendly smile. She came over to me and asked if my food was OK. I nodded and she headed into the kitchen with the stack of crockery. Outside, a lorry delivered drinks to a scruffy off-license across the street. The tarpaulin covering the trailer rippled in the wind as the driver dipped his head into the rain while hefting cases of beer cans through the shop's side door.

Absent-mindedly, I picked at my nails as I watched. My mind absented itself. Zoning out as it moved from one grey scene to the next. I poked my phone, checking I hadn't missed a message. Instead, there were just emails from the university. A reminder that graduates must return library books, an invitation to join the alumni association and a notification that the electronic doors in my former department were malfunctioning, again.