A Friendly Game

Story Info
Long time friends and an innocent game of Truth or Dare
4.3k words
4.36
95.9k
19
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Authors Note: I have known Jess for ten years and have stayed in contact on and off for most of that time. Although I had not seen her in several years there had been a sexual attraction there since the beginning. We had met due to the actions of out then partners who wanted to spice up sexual relations. Several adult games had been played, sex in front of the other couple, and even a short kisses between us.

*

It had been a long time since I had seen Jess and I was incredibly nervous to see her again. She was in town and had wanted to catch up. Her schedule had been so crazy that we decided to just get pizza delivered and chill at my place. I was waiting for the pizza guy when I heard the car pull into the drive way. Looking out the window I seen it was Jess and she popped out of the car wearing a very cute button up pink top and jeans. I was wearing a hoody over my tee shirt and jeans so I felt a little better knowing she was not dressed up real nice. She had a bag in her hand as she came up to the door which I was opening to let her in. I pulled her close into a big hug and could feel the warmth of her body against mine. " I brought strawberries for dessert," she was full of energy it seemed.

I was planning on us having ice cream, "I have some chocolate syrup in the fridge we could use." She thought it was a great idea and we settled down in the living room. Jess stretched out on the couch while I sat down in my favorite recliner. The pizza arrived and we ate, chatted, and caught up with each others lives. I brought out a plate that I cut up the strawberries on and drizzled chocolate syrup over them for her. We were relaxing and Jess had eaten one when she said I should try it. "They are so juicy and sweet," she stepped up to me and placed the strawberry to my lips. I open my mouth as she leans over giving me a glimpse of her smooth skin. I bite into it as she giggles and quickly backs up to the couch.

The food was great and dessert had been very interesting. Chatting with Jess was bringing back a lot of old memories and just seeing her was arousing the hidden feelings we had shared. We were watching some lame reality tv about being on an island when it all started...

I was sitting in the recliner seeing her all stretched out on the couch. I kept looking over at Jess and thinking how I wouldn't mind being stuck on a deserted island with her. Jess is about 5'7" and weighs about 125 lbs with beautiful, long, reddish hair. She keeps shifting on the couch, self conscious of her weight because of the having been pregnant before but all I see are the sexy curves her body has gained thanks to those daughters. I keep looking over at her and naughty thoughts are running wild in my head when she bursts out, "Truth or dare." She's giggling as she looks at me and I can tell she is as bored with the show as I was.

Not sure how serious she was I said ,"Truth," but figured I would play along if she really was game. She had a wicked little gleam in her eye as she said, "Were you just fantasizing about what it would be like if you were stuck on a deserted island with me?"

"Yeah" Damn this girl could read my mind as I laughed out loud at the how naughty my fantasies had been. "So truth or dare, Jess?"

"Dare," she grinned.

I was at a loss, not sure how serious she wanted this to be but wanting to take it as far as possible. "Come on," she urged, "dare me! Ask me something," she was really enjoying tormenting me. "How about daring me to spread chocolate syrup on my breasts with my fingers, then play with my nipples and lick my fingers off in front of you."

She had my mind all over the place with that visual but I found my voice," I dare you to show me the color of your underwear." She stood up off the couch and popped the button on her jeans. She turned to the side as I heard the zipper slide down. Then pulled the flap aside to show me a glimpse of her pink panties from Victoria Secret.

"They're cheeky boyshorts," as she dropped back onto the couch without redoing her pants, " so truth or dare?" Playing it safe I went truth again. " Well lets see, Do you sit and try to imagine what I look like naked?"

It was a real good question. I told her how I would sit back thinking about what I remembered seeing of her that night and what she looked like naked now. She listened intently as I spoke and went truth for her next turn.

"So do you go natural, trim, or shave completely?" The question was burning in my mind as I looked over at the pink patch of underwear I could still see.

"Well my life gets a little crazy sometimes and I just trim it down to a little patch. Most of the time I shave completely especially when I want to be sexy for someone. Truth or Dare?"

"Ok, I go truth again"

"Fun little twist, same question to you. Its always fun to hear what guys do."

"That's fair but you can't keep doing that," I said and stuck my tongue out at her. " I actually keep it trimmed pretty short and think it looks a little weird if I shave it all off."

"I agree, guys look better trimmed and I'll go truth."

She had my attention completely now and my mind had found its course, " so where is your favorite place to masturbate," I asked knowing that this game was just heating up.

"In bed actually," she laughed but I could see that I had sparked something in her imagination.

I went with truth again and the idea of masturbating must have stuck in her head, "Have you masturbated to the thought of me since you found me again?"

"Good one Jess and yes I have, Truth or Dare?" I had thought of nothing but her since we had starting talking again recently. She went truth and I knew my question even before she answered. "When was the last time you masturbated to thoughts about me?"

I see the flush in her face as she said," Yesterday. A quick one with a toy but yeah it was after thinking about you." I was really excited hearing this and volunteered to go truth again. She laughed saying, "Old school. How about thinking of me while you were having sex with Alisha back when we first met?"

Alisha was my ex who I was dating at the time when we all got together and I was more than willing to admit the truth, "Yeah there were times when having sex with her that I would think of you so that I could finish because the idea of you made me cum so easily. So your turn."

"Truth is a bit easier so I'll go truth again," she said but I could tell these confessions of how we pleasured ourselves to the thoughts of each other.

"I'll go old school too. Have you ever pulled out the red thongs and thought of me?" She had wore the red thongs when all of us had first met and the view I got of her in them had been burned into my memory.

"Yes. I have been going through my drawers before and come across them and be like awe Bill." She was getting really excited by this turn of conversation and had unbuttoned the top three buttons on her pink shirt. "Now you turn Bill, Truth or dare?"

I was feeling a lot more adventurous and decided, "Dare."

"Ok, pretend we're in a club dancing and show me your best dirty in the dark moves."

"You have to stand up so I can show you," already running the entire scene in my head and Jess stood with a smile. I got up close to her and slid in behind her barely touching. Sliding my hands down her sides while moving my lips right next to her ear, "Imagine we are in a club with some fast beat music." My breath is warm and I can tell it is exciting her. I use my hands to get her to start swaying her hips to the music, " The music is blaring as we stand in the crowd with the lights flashing so we can barely see," my hands slid back up her side and caress the side of her breast. "Then when the lights go real low," lowering my voice as I say this my hand grasp your hips and pull your ass snuggly into my cock. Jess jumps with a series of giggles and pulls away. "Truth or Dare," I sit down knowing that I just scored big in the game. She went with truth, "So Jess if I could kiss you on one place and one place only on your body, where would you chose?"

" Well I love to have my neck kissed but no trashy hickies," she laughed and paused. "But I would say my lips of course. There are so many connections you can get from a kiss. The good ones can just make you melt." Her answer was arousing in more than a sexual way and I decided to go with a dare. A real devious smile lit up her face, "Okay. I dare you to lean in close like you are gonna kiss me but don't let our lips touch. See how close you can get, so we can feel each other almost, but resist the urge to actually kiss."

I got up and walked over to the couch. I sat down close to her, my body just inches from her, and looked into her eyes. They are a beautiful hazel but unusual in an exotic way. In some ways you can see more green in them or brown others but they were mesmerizing. She was looking directly into my bluish gray eyes with the same intensity as I leaned in close so that our lips were just barely separated. I could smell the lingering mixture of strawberries and chocolate as we sat there for only a few seconds but felt like ages. I was in agony resisting the desire to close the last little tiny gap not taking my eyes off her. The it was interrupted as she burst into giggles again, "That was intense, dare me."

"I got a dare for you," as take my finger and slide it through the chocolate syrup that is left on the strawberry plate. I put small smears on each side of my neck, then some in the hallow at the base, and then put a small dab that just barely touches my bottom lip. "I dare you to lick all the syrup off of me."

She slid up next to me leaning in close so that her body was pressing into me a little. She moved her head to the left side of my neck and I felt the warm glide of her tongue as she licked the chocolate off. She leaned back slightly and looked at me with a slight grin. Pushing her hair across her face she leaned in to the right side, licking off the chocolate and moaning lightly. I began to wiggle as my cock began to grow which caused Jess to lean back and look at me. She pushed back my head and began to kiss the hallow at the base of my neck, licking out the chocolate. She comes up licking the syrup from her lips and places her hands lightly on the sides of my face. She kisses my chin and then my bottom lip lightly licking off the syrup. I lean in to kiss her lips when she quickly pulls away. "Okay, your turn truth or dare'" she was so casual like nothing had happened.

I lick the chocolate off my finger," Well you were close to completing the dare." Two can play this game, "And I'll take a dare this time."

Jess did not like me winning I could tell as her mind worked for just a second before saying," I dare you to kiss my neck from my collarbone to ear," as she traced the path with her finger," without touching me anywhere else."

I got close to her but made sure that my body was not touching her and leaned in slowly. As I got close to her collarbone I could smell her perfume, it's Love Spell by Victoria Secret. The scent is lingering and intoxicating as my lips make contact with her skin. My kisses are slow and deliberate as I move across the shallow dip at the base of her neck. My lips are having an effect as I hear her begin to moan lightly again. I'm moving up her neck as my hand slides across to her side. It slowly moves down her side and onto her hip as I move up close to her ear. Then without warning she pulls apart, "Tsk Tsk, you touched me," giggling the whole time. I was stunned and had not even realized that I had done it. She had gotten even pretty quick but I could see the color in her face that she was really excited. "Dare!"

"Oh brave girl, I dare you to suck on your finger like you were giving me head," was my reply figuring I was gonna push her limits after her burning me on the last dare. She started slowly holding up her hand with her index finger sticking out and swirling her tongue around the top like a lollipop. She kept working her tongue up and down her finger slowly making it all nice and wet in between swirls at the top. Every move was teasing until she slid her whole finger deep into her mouth and slowly sucking as she pulled it back out. She went up and down several times and came up with a lick and twirl of her tongue on the top. She was looking me in the eyes but they kept dropping to look at the growing bulge in my pants. She seen the growing desire in my eyes apparently cause she just burst into giggles again.

Taking a break to see exactly where it was going I decided to go truth. Jess was in no mood for that, "So what is your weakness in a woman? Something about a woman or that she does that makes the captain tingle?" while playing with the buttons she had undone on the top of her shirt.

"I think it would be when she does something when she knows I am looking that says look at this like bending over in front on me." Jess seemed to take all this in with a mischievous grin. "So truth or Dare, Jess?"

"I think I will go with," after a long pause, "dare."

Deciding it was my turn to get back ahead of her, " I dare you to demonstrate your favorite sexual position."

"Well, I'm pretty simple," she said with a giggle, "but I think I may need your help with this one."

"I'm at your service, pretty lady. You can use me as a prop." She grabs me, pulling me down onto her while moving her leg out of the way and laying flat on her back. We are in the classic missionary position but it seems Jess is going take it a little further. She pulls my face down until our lips meet. It is like a jolt of lightning that ignites our long hidden passions. Our kisses become more and more bold and her tongue slips into my mouth. Our tongues move against each other like we have been kissing each other forever and not just for the first time at this passionate level. Our tongues continue to play as our hands roam over each others bodies. I pull back and kiss her collar bone while slowly working my way up to her ear whispering," Is that better?"

She is moaning with pleasure and makes a sound saying yes. We continue to kiss for several more minutes before I pull back and sit down. Pulling Jess up with me as I go, she quickly swings her leg over and sits down on my lap. I pull off my hoody and tee-shirt in one swift motion and resume kissing her sweet lips. My hands slide up her side and under her shirt gliding across her smooth soft skin. I move one hand behind her back and pop the clasp of her bra while the other slips under the front to caress her breast. Jess is a small girl and is always self conscious of the size of her breasts. While they may be small, they are beautiful like her and perfect for her body. I cannot see them but they are soft smooth with perky nipples. Jess leans up for a breath and of course a giggle, "So was it worth the wait?"

"More than you can imagine but I do believe I'm two layers ahead," I teased as I feel shifting on my growing erection. She hops up with her giggles only intensifying. She drops her pants and gives me a close view of the pink boyshorts that have been frustrating me all night. I can even read the little Victoria Secret logos on them I am so close. Slipping her hands into her shirt she pulls out her bra like some kind of magic trick which I see matches her panties as it lands in my lap.

"Even now," she climbs back onto my lap and resumes kissing me. I slip my right hand back up her shirt and continue to caress her lovely breasts. My other hand grabs her ass firmly enjoying the soft nice curves of it. I pull her tightly against me and feel the warmth coming from between her legs. We continue to kiss and savor the feel of our bodied against each other. My cock is straining against my jeans and I am ready to see how far she will go. "One more layer," I pant?

Jess rolls off me and onto the couch before I know it. I stand up and unbutton my jeans. I was expecting her to remove her shirt as I slide my jeans off but instead she lifts her legs pulling off her panties. Leaning back she beckons me as she lays there with her legs spread slightly. I had dreamed and fantasized about what she would look like. Cleanly shaven with small lips that glisten from excitement, she is perfect. She looks at me, "I think you have caused a reaction."

"I'll have to check and see," as I take my finger and rub her lips. Sliding my finger up and back, over her clit, before dropping down to her wet opening. I gently push the tip of my finger in feeling the warmth and tightness of her. I crawl back between her legs with only my boxers separating us. I can feel my cock pressing against her which only makes her moan loader. I begin kissing her collar bone again and working my way up to her ear. Our mouths meet again and our tongues play up against each other. My erection is growing harder and I know I am ready.

I stand up," I think you caused too," dropping my boxers to the floor as my cock springs forth. Jess gets an eyeful of my cock poking straight at her as she slips off her shirt. At seven inches and good girth she seems to approve readily of "my captain" as she likes to call it. Getting my first good look at her entirely naked body and those lovely breasts, I smile my approval," You're Beautiful." I lay back between her legs, my cock pressing against her feeling her warmth and wetness while I kiss her heavenly lips. I think I could kiss her forever as our passions are exchanged in those long deep touches. Our bodies move slightly against each other as out hands and lips caress each others body. My cock has pressed and rubbed against her lips before settling at the entrance to sweet body. I slowly push him in just a little before stopping savoring the feel of her. I continue to slowly push my cock into little, pulling out, then pushing in a little further. I continue to do several times until eventually I bury my entire cock into her.

Enjoying the feeling as our bodies connecting as our movements naturally match. It is like we are made for one another as the intensity of the sensations spread through our bodies. Sliding in and out of her is pure bliss, she is so tight and wet. The feelings are so amazing that I want to cum then and there just to feel my semen shooting deep inside her but I resist. Wanting to bring her pleasure, I pick up the pace which she matches perfectly. Our bodies rock together as our hands intertwine above her head and I use it to push deeply into her. For a moment she falls out of rhythm, "Everything okay?"

She nods and pants, her breath coming fast and shallow. The exact opposite of my motions as I slid slowly and deeply into her, savoring the feeling of her. Enjoying the feeling of her caressing my body and the look of passion on her face. The pace varies occasionally as I lean back and kiss her nipples, which stay hard from her arousal. Finally, I can take no more and pull out, laying back onto the couch exhausted.

Jess quickly steps over top of me and lowers herself down onto my cock. The feelings are so intense as I see the pleasure on her face as my cock fills her up. The position is great as I can play with her breasts with one hand and grasp her ass with the other. The best part is Jess picks the pace and apparently she wants it bad as she moves rapidly, sliding up and down the length of my cock. I love the feeling of her riding me and the pleasure she gets from it. I can see she is building up from this and gives me a new reason to enjoy the position. She bends down so our bodies are pressed together, kissing me deeply, and being so flexible her pace never slows. As her breath becomes rapid and shallow again, I can what she has been building up to. As her orgasm rocks her body, she buries me deep inside her and I can feel the muscles contracting in pleasure. I can feel her tight wet muscles grasping and clamping my cock firmly while I fight the urge to release a load of cum deep inside her. I am enjoying this too much to cum and thankfully Jess has stopped moving as she comes down from her orgasm.

12