The Convention
The summer after my senior year of high school was ripe with adventures and shenanigans. I had a car and a driver’s license and I used them to the fullest. I enjoyed my abundant free time and resources, and so did my girlfriend. But of course, you all aren’t here to listen to me relive a golden time; you came to hear about someone get tied up and maybe more.
It happened in July, the weekend of my 18th birthday. My girlfriend and I were heading to an anime convention together, along with my friend Joe and his girlfriend Jess. Now, at the time I was dating a girl a couple years older than me who I worked with, we’ll call her Violet for her privacy. Anywho, Violet was a cute girl, tall and thin, with curvy hips and buttocks, and a pair of lovely perky B cup breasts. She kept her dark brown hair short, in a pixie cut of sorts, though she kept her bangs long and to one side, sometimes covering one of her gorgeous hazel eyes, which she knew I loved.
This story begins on Friday morning, we all met up early so we could check in to the hotel early, and beat some of the traffic for the Con. At around 7:30 we left, in two cars. Violet rode with me, and Joe rode with Jess in her car. The road trip, not accounting for traffic, bathroom breaks, gas, and whatever other delays, was about 3 hours.
The moment we got on the highway I cranked up my AC/DC compact disc and we began our favorite game to play in the car. The game consisted of us constantly teasing the other seeing who could carry it the furthest. I was often at a disadvantage for this game since I was driving, but that didn’t stop me. She started us off by grabbing my thigh, slowly working her hand up the outside of my shorts trying to get a response from me. I of course did not give her the satisfaction, and instead kept a stoic face as my hand went to her tummy; her most ticklish part. She squealed of course, giggling and biting my hand playfully. This only egged me on as I grinned, suddenly tickling her thighs, causing her to jerk and thrash under my expert tickling skill as she couldn’t help but laugh and squeal. My merciless tickle torture continued until she played her trump card: her hand found its way between my legs, cupping my crotch through my shorts. I froze and she grinned, she knew my weaknesses, in these thin shorts, her touch had caused a slight erection which she stroked through the material, chuckling a bit at the power she had over me with this, especially given that I also had to focus on the road, which limited my options for retaliation. I sat there for a moment as she circled the tip with her fingernail lightly, which if you have never had that done, is an incredibly erotic feeling. However I was not to be outdone; I slipped my hand into her tank top, my warm hands a shock to her almost always cool flesh. My hand began massaging her breast in a circular motion, my fingertips moving over her large areola as I felt her nipples begin to harden from the attention. She gasped and her face turned a shade of crimson, which was in all honesty a cute look for her. She couldn’t help but stifle a moan as I gently worked my fingertips around her areolas.
In that moment, with me winning our little game, and her trump card already played, she made a bold move that I had not expected. Her cold hand slipped inside my shorts and my boxers, grabbing hold of my now hardened member. I was a bit shocked. We had been dating for months now and had a fairly physical relationship, kissing, hugging and groping had been fairly commonplace for a while, but this was a first. We had never actually touched one another’s genitals like she was now. I could tell the realization of what she had done had dawned on her, as her grip slackened a bit, and she looked away, too mortified to continue, but also couldn’t stop now that she had come this far. I felt her fingers tighten again as she began jerking me off slowly. Her cold hands felt good against my warm member, for all the world I didn’t want her to stop. It was strange, the feeling of someone else’s hands, but it was also incredible as her small cool fingers maneuvered up and down me that I almost forgot that we were playing a game and that I was losing. Only through sheer stubbornness and hatred of losing was I able to overcome the trance and react in kind and slide my hand into her shorts. Once I did this though I was greeted with a surprise. I had intended to slide my hand between her shorts and panties, as my hand reached in, I discovered she was not wearing said undergarment.
We exchanged a glance. As she, still blushing furiously and barely able to look me in the eyes, stammered “Surprise…”
I couldn’t believe she had gone commando. At the same time I couldn’t waste this opportunity. I found her clitoris with my probing fingertips and heard her gasp. I then began trying to remember the research I had done on such matters and began to rub in a circular motion, enough pressure for her to feel, without causing pain. It was a fine balance that I apparently had a natural talent for, as soon she was squirming in her seat, the nylon seatbelt allowing no escape from me. We continued like this for about ten minutes, driving down the highway like nothing was happening while both pleasuring one another, wondering how long we could do this, but also not wanting to stop. That question was answered faster than we thought, as suddenly I felt her twitch and jerk against my hand as her warm fluids squirted onto my hand. Wordlessly we retracted our hands, no words were needed.
The rest of the drive went uneventfully, save for a couple potty breaks. We arrived on time and checked into our room. I will have to stop here give myself a pat on the back for this, as I managed to find a suite in the hotel that was practically attached to the building the con was in, the weekend of the con, for only $200 for the two nights. Anywho, we checked in and lugged our bags up the elevator and into the room. Right after opening the door was a long hallway leading into the main area, complete with a couch and TV. On the right and left sides were the bedrooms, and the bathroom was in the hall on the left. Violet and I took the room on the right and set our bags beside the bed. After that we all began getting into costume; the doors of the con opened at 1 and we wanted to be there for that. I was wearing a black long sleeved shirt, and grey slacks with a pair of black shoes; a simple Karkat costume for those who know who that is. Violet was wearing a white blouse, tucked into a pair of black slacks, and a red wig. I don’t remember who she was cosplaying, but I do remember she was wearing heels that made her taller than me.
Anywho, the con began and we entered, occasionally people wanted pictures with me, more often than not people wanted to take a picture of Violet. I don’t blame them, she looked absolutely stunning. We walked around for a time, looking at various booths and panels. Time passed and eventually it was about 4:30. Violet wanted to get dinner, so we split off from Jess and Joe to get dinner, since they had several panels they wanted to go to. After grabbing a bite to eat at a Japanese restaurant we returned to the hotel to rest up before anything further. This is when things got interesting, so for those of you mindlessly scrolling for the action, stop here. (You know who you are)
She was sitting on the bed when I got out of the shower, having to wash of some gray face paint I was wearing, not to mention the sweat of wearing black long sleeves in the middle of July. I emerged from the bathroom in my shorts from earlier as she was setting my phone down. She set her phone down and suddenly embraced me. Not being an uncommon thing, I hugged her back and kissed her cheek. Then she whispered in my ear: “You know…you didn’t cum in the car…”
I froze for a moment, not nearly expecting such a blatant advance. “No, but then again, you went off a little early.” I pointed out, teasing her with a slight grin.
She giggled and traced a finger over my chest “I guess that was my bad, huh? However will I be able to make it up to you I wonder…?”
I was so unbelievably excited by this I could barely contain it, already a bulge was forming in my pants. But being the dork I am I responded with “Indeed. We should probably get ready; Joe and Jess will be back soon…”
She evidently had seen this coming and grinned “No, actually they decided to hit up a few more panels and won’t be back for a few more hours, especially since I told them we needed to be alone for a bit.” She clearly had planned this out a bit. “So Mr. Frey, what can I possibly do to make up this morning up to you?” this was single handedly the most erotic thing she could have said given pursuit of a career in teaching.
I grinned, if she wanted to do this, we could do this. “Well there is one thing…” I said slowly, leaning in, planting a kiss on her soft lips. At this point in time I had already discovered my interest in tying people up and other such things, and had even discussed it with her a bit in a rather general way.
She grinned and pecked me on the lips before stepping back “I think I know what you want.” She leaned back grabbing a small bag off the table and handing it to me.
I looked inside eagerly, wondering what it was. Inside was a dream come true: a blindfold, a red ballgag, a couple bandanas, a bundle of rope, some condoms, a bottle of lubricant, couple pairs of handcuffs, and a collar with a leash. I looked back up from this treasure trove at her in awe, I hadn’t guessed she had this sort of stuff, but the gag and collar looked like they had been used, as did the rope. She winked at me and kneeled in front of me, placing her arms behind her back in preparation; no words were needed. I took a moment to appreciate that she had changed out of her slacks into a short plaid skirt with black thigh highs, and had unbuttoned her blouse significantly enough I could see her red bra beneath. I took out the collar first, buckling it around her neck with great care. I attached the leash to it as well, letting the small chain dangle for now. I then proceeded to use the rope to tie her wrists behind her, looping the bundle and creating a firm bond without cutting off circulation. I finished the knot and then blindfolded her. I helped her to her feet gently, as this would be a better position for what I had in mind next.
Once I had her on her feet I stepped behind her quietly, wrapping my arms around her suddenly, causing her to flinch a bit, since she couldn’t see. I slowly slid my hands up her sides as I kissed the side of her neck; something I know was a hotspot for her. The result was instantly gratifying as she couldn’t help but to moan softly and lean into me, craving more. I was thankful for the amount of literotica I had read at this point for being able to give me some helpful tips. I kissed lower down her neck to her collar as my hands groped her perky breasts softly, massaging them gently, my fingers rubbing over her nipples through her bra in a circular motion. Once more I was rewarded with a moan and a slight gasp, a good sign I was on the right path. I moved my lips up a bit, suckling on her neck until I left a mark, known by many as a “hickie”. I unbuckled her bra, though left her blouse on, as I loved that schoolgirl look. I gently bit the side of her neck, raking my teeth gently against her cool flesh, as my hands slid down her stomach to her skirt where they stopped, an intentional tease. She was panting a bit, and had started using her hips to rub her ass against the obvious bulge in my pants slowly. I grinned and bit her earlobe gently, tugging slightly before I released her ear and removed myself from behind her, leaving her blind and clueless to where I was. I was enjoying myself probably more than I should, but it was an incredible giddy feeling to play with her like this, to have her helpless and in my arms.
I stepped in front of her now, pressing my lips against hers passionately, while wrapping my arms about her hips, pulling her against me. She immediately slid her tongue past my lips hungrily, searching for my tongue, her hips grinding against me. I responded in kind, my tongue finding hers and pressing it back a bit. Honestly from here I had no Idea what to do, I was, and still am not a very good kisser, frankly I was just impressed I had managed to french her without slobbering all over her face or accidently biting her. She began going at me ravenously with her tongue, flicking it here and there. After a couple awkward seconds of this, she realized I couldn’t exactly keep up, so she settled for sucking on my tongue gently. This continued for a few moments before I pulled back slightly, causing her to lean forward, seeking out my lips again. I taunted her, leaning in to kiss her, my lips barely brushing against hers before I pulled back again, leaving her kissing nothing but air. She smiled at my teasing, enjoying this almost as much as I was. I began kissing her neck again, leaving a trail of kisses down her neck to her breasts, kissing my way down the right first, pausing to gingerly kiss her nipple before biting softly. Her nipples were already erect from the stimulation, and were sensitive, causing her to tremble as I kissed them. I moved from the right to the left, giving the other side similar treatment. She was panting now, as I came back up, biting her lower lip tauntingly. She smiled a bit and tried to take advantage of this, and tried to kiss my lips again; but I was faster and moved my head out of the way. She whined a bit, grinning a bit “You are such a tease.” She giggled.
“So? You know you love it.” I responded with a grin before kissing her again, giving her the chance to kiss me back this time. She took advantage of this and began to kiss me ravenously, invading my mouth with her tongue. I tried my best to keep up, but was terribly unsuccessful. After this she pulled away this time, before whispering in my ear “Can I try something?” I agreed, at this point I would have done just about anything for her. But to my pleasant surprise, she slowly shifted to her knees and began to kiss around my crotch region. She missed a couple times, trying to find me, but eventually her lips found the bulge in my shorts. “Help?” she asked, smiling up at me. I happily undid my belt and removed my shorts without hesitation. I then pulled my boxers down enough for me to pull out my member, already erect and ready for her.
She found it quickly and kissed the tip sweetly, before kissing up the shaft a bit, before bringing herself back down to the tip. She licked it a few times, her tongue flicking the underside, just below the head, where there is a sensitive vein. I had not previously been aware of said vein, but now I was very much aware of it, and was happier for it. She then took me into her mouth, sucking on the tip first, then slowly worked her way down until she gagged a bit. I pulled out immediately, worried about her, but she shook her head “I’m not done yet.” She said with a smile before going back down on it. She could not fit my entire length into her mouth without gagging and made it about halfway down, but even that felt incredible, especially when she began to work her tongue around me while I was in her mouth. My legs felt like jelly, as a virgin who had only ever felt the touch of my own hand, it felt otherworldly. I ran my fingers through her hair, for lack of anything else to do. I realized that with her on the floor, there was little I could do besides let her pleasure me. I certainly could imagine worse, but I still wanted to do something for her while she made me feel this good. I slid my bare foot between her crouched legs and lifted up a bit, my toes rubbing against her damp panties. She moaned a bit around my member, which caused a slight vibration that felt pleasant in conjunction to what she was doing. I continued to rub her through the panties as she sucked; causing more moans and in turn more vibrations. I can’t remember exactly how long we stayed like that, I’d gander at close to 45 minutes before I finally felt close. Being the gentleman I am I warned her of my imminent ejaculation. She pulled off and licked the slit a few times and pushed forward her chest, indicating what she wanted clearly. I found no reason not to and within seconds I had cummed on her exposed breasts, though some made it on her chin. She eagerly licked at the small glob on her chin and smiled “ Love you Toby.”
“I love you too.” I replied, leaning in and kissing her forehead. I then scooped her up in my arms and set her on the bed. “ Now let me return the favor.”
She gasped as I picked her up, not exepcting that. “Toby, you don’t have to-“ I didn’t let her continue as I pressed my lips to hers. I untied her hands and retied them above her head for comfort. I then pulled away from the kiss, softly biting her lip. She blushed, unable to speak as I brought the ball gag to her lips and she opened her mouth invitingly. I did not buckle it in too tightly, as I was very concerned about her safety, and also if I hurt her somehow, I wanted her to be able to push it out to tell me.
I then kissed her gagged lips as a final taunt before kissing down her jaw, then to her neck, where I left a hickie on the other side. I could feel her heartbeat increase a bit as I kissed lower down her body, careful to avoid the mess I made. I finally stopped at her now soaking panties. I pulled them off slowly kissing her exposed nethers softly. Her breath quickened, and she tried to move closer to me.
I started by licking up from the bottom of her slit. My tongue barely grazing her, just slight touch. I then went for her Clitoris; at this point I was glad I had read an article on how to do this properly. I did my best to wrap my lips around it and suckle as the article had said. I received immediate results. She gasped and moaned as I pulled her small bump into my mouth, using the pressure to stimulate it. I remembered the article mentioned using my tongue, so I tried that. I flicked my tongue over it, going multiple directions, figuring out which worked best based on her response. I soon found the vertical pattern earned more of a positive response and stuck with that for a few minutes. A few seconds in I began to realize that this particular motion with my tongue was much like the one I used in band when playing trumpet to change the octave of my pitch. With this in mind I grew more aggressive with my strokes, and saw immediate results. Within 5 minutes she had reached climax, squirting a bit, catching me off guard. After realizing that I had brought her to orgasm, I went in again, this time targeting the slit. I ran my tongue down to her slit and lapped at it a few times, not sure what to do from here. After licking and kissing it a few times I gave up and went for her clitoris again, performing the same actions as before. While I had tied her hands above her head, I had not secured them to the headboard and so she had the ability to bring them down and push my head down. I was surprised at first, but also flattered that I was this good at it. That’s when she began to scratch my head, her nails dug into my scalp as she moaned loudly into the gag, her breaths short and rapid, and her hips grinding against me. This time she managed to last around 10 minutes before I brought her to orgasm.
Before I could go down on her again she pushed the gag out “Toby, I need to rest, can we stop now?” I was a bit disappointed she couldn’t last more, but I hid my disappointment as I removed her gag and blindfold. When I went for her wrists, she pulled them away, shaking her head with a smile “No, I want to stay like this for a bit.” I couldn’t argue with that logic, and so I cleaned her up with a towel before tending to my bleeding scalp. After I had finished I climbed into bed with her and we cuddled for a few hours. Unfortunately I had to let her go before our friends came back. But on the bright side, this was not the last time.