As I opened my eyes on Friday morning and took in the college dorm room that had been home for the past week, I couldn’t help but smile, as all of the images and sensations of the night before flooded back so vividly. My right hand began to move its way down to touch myself once again, but before I could indulge, your text arrived: “Are you awake, yet?”
“Yes!” I responded instantly, delighted to hear from you so soon.
“How was your night?”
A few more quick texts back and forth, and then you asked if we could talk. I eagerly dialed, pulling on just enough clothes to be decent so that I could go outside and talk to you freely, away from the thin walls separating me from the colleagues with whom I was sharing the apartment.
I couldn’t wait to share with you what I had done, just how much of a slut I had been to please you, and of course pleasing myself in the process. But for the purposes of this written account, I should first share a bit of background before I describe that wild Thursday night.
It was a weeklong conference hosted on a university campus that will remain nameless to protect the innocent, as well as those less than innocent. I had traveled there with three colleagues, all women who proved to be lovely roommates. As I shared with you earlier that week, I was - at 30 - not only the youngest of the group, but also the only one without a tattoo; that still makes me laugh. Our days were largely spent apart, attending our separate workshops and meetings, but we would typically gather in the evenings for a meal.
I came into the week knowing that I would not do anything to do my professional relationship with any of these colleagues, but also that you had challenged me to take advantage of the conference to continue the exploration of my slutty ways. My goal was to have at least one, but preferably many, encounters to tell you about. “Pictures if possible,” you had said before I left.
My first opportunity came on Monday evening, the first night of the conference, when I attended a reception hosted by the conference. I was there with my colleagues, but thankfully we split up early on and began mingling with other attendees. I sipped my wine, responded to a variety of naughty suggestions from you via text, and before long found myself at a round standing table with a man whose nametag read ‘Jon’.
We chatted, but I remember very little of what he said aside from where he worked. He stole numerous glances at my cleavage, and found every excuse to touch me on the arm or shoulder during our conversation, so I decided to make my move. I reached down, glancing around to make sure nobody was watching us, and grabbed his crotch. He seemed a bit surprised, but did nothing to stop me, and so I began stroking, slowly at first and gradually faster.
I was already tipsy, but took one more sip of my wine, and then decided to try bringing the encounter to another level. I stopped stroking him, and when he made eye contact, clearly disappointed, I motioned for him to follow me, and led him to a long hallway which led to the restrooms. I pressed him against the wall and resumed my fast stroking of his still-hard cock, all the while listening to the room where everyone was gathered. I was simultaneously afraid to be caught, but also turned on by the risk.
When I was confident that no footsteps were headed our way, I quickly crouched down, unzipped his slacks and pulled out his cock, and he came almost instantly. It was all I could do to get his 4-½ inch long but fairly thick cock into my mouth in order to catch every drop of cum, but I did. I know you would have been proud. He went back to find his colleagues, and I mine. While I made small talk with them, I couldn’t think about anything but the taste of cum in my mouth and my throbbing clit.
After that first bit of excitement, the following day - Tuesday - proved uneventful. I began my Wednesday assuming it would be as well, but was quickly in for an interesting surprise. While my roommates slept in, I left the room just after 6am and walked to the Starbucks that I was very thankful was just a few blocks away. Coffee in hand, I then explored a bit further, finding a quiet park on the water with a small beach.
Given the early hour, I wasn’t expecting to see anyone, but as I walked towards a small parking lot near the beach, I noticed one car parked, and could see two people inside. As I drew closer, it was obvious from the motion of the silhouetted figures that the people were not just sitting and talking. I was witness to either a hand job or a blow job, or a combination of the two. I had no intention of interrupting their encounter, but the closer I got, I recognized the profile of the man in the driver’s seat as that of a fellow conference attendee. My curiosity now heightened, I couldn’t help but glance into the car as I passed it. I kept a decent distance, but as I was walking on a gravel path, my footsteps attracted their attention.
The man saw me first, and immediately turned bright red. He obviously recognized me as well, and as he turned towards me, I could see that he was wearing his conference name badge. As I mentioned, I hadn’t intended to interrupt them, and it was obvious they didn’t want to say hello, and yet the man seemed to feel obligated to cover for their behavior by waving me over to the car to say hello.
The woman in the passenger seat reached down for something, which I later realized was her jacket, to toss into her companion’s lap - undoubtedly to cover the evidence of his unzipped slacks and perhaps even his still-hard cock. When I reached the car and leaned in to say hello, I noticed that the woman - who I guessed to be in her early 20’s to the man’s mid-50’s - was also wearing a conference name badge.
A quick glance to both name badges - his name was John and hers Whitney - confirmed that they were from the same institution. It didn’t take long for the source of his painfully awkward embarrassment to become clear - obviously they were teacher and student. I wish I could remember my exact words, because I rarely think so well on my feet, but I managed to express to them two facts: I had no objection to their public meeting for sex, but I also knew that I now held something over them that I might choose to use for my advantage. Whitney, her wavy brown hair tousled from their encounter, blushed now as well, although she didn’t look as terrified as John.
My favorite part of the story, as I’m sure I told you at the time, is that after I walked away, they got right back at it. It couldn’t have been more than 30 seconds after we said our goodbyes and I walked away that I turned, looked back, and noticed that the car windows were beginning to steam up.
That evening, I had a networking dinner to attend at a pub off-campus. My colleagues and I drove together, and given their presence and the relatively small room in which we were meeting, I didn’t expect to have much opportunity to be slutty for you. There was wine and mingling for about 45 minutes, during which I enjoyed texting you, before we were ushered to tables where our dinner would be served. I was a bit disappointed to find myself sitting at a table with just women. Ah well, I told myself, I’ll enjoy the conversation and try again tomorrow to be naughty.
There were five of us squeezed around a small round table - myself and two of my colleagues, a very entertaining older woman from Scotland with fiery red hair, and a shy young brunette who sat next to me, her nametag reading ‘Hello, my name is Jen.’ I found myself working to bring her into the conversation, as she was so quiet, but she did begin to loosen up after her first glass of wine.
Before long, into the second glass, we had found some common areas of interest to discuss, shared some laughs, and she had even touched my arm a few times during the conversation. I was proud to have pulled her out of her shell, but didn’t think much more of it. That is, until the other three women at the table were occupied with their own conversation, and a now quite tipsy Jen leaned in and told me that her husband loved tits like mine - full and firm - and that she always wished hers were bigger.
I couldn’t help but glance down at her chest, which I hadn’t done up until that moment, and while her tits were perfectly lovely in their perkiness, they were probably no more than an A-cup. She was petite anyway - 5’2”, about 110 pounds, and so her boobs looked perfectly good on her frame. But as soon as she’d said what she’d said, she kept staring at mine, obviously jealous. Jen was probably in her late 20’s, with a cute, girl-next-door kind of look. She was wearing a black bra and camisole under a sheer white blouse, and slightly baggy jeans.
Although I was surprised by the direction the conversation took, I still didn’t think it was an opportunity to have much of a story for you, given the crowded professional environment. After all, I was the designated driver to take my colleagues back to our rooms. Undoubtedly, I’d soon have to say ‘good night’ to Jen, perhaps never to see her again.
As the event wound down and people began heading for the exit, I excused myself from the table to visit the ladies room. Jen quickly did the same and followed me. Again, naive as I apparently am, I didn’t read between the lines. At least not until we found ourselves alone in the restroom. We took care of business, washed our hands, and then Jen moved between me and the door, and asked, with a disarming directness, if she could see my tits.
She put her foot against the door, so that we’d at least have some warning if someone else tried to enter. I smiled, and without breaking eye contact, pulled down my camisole and bra to free my tits. Her eyes immediately dropped to my erect nipples, and she reached out to feel them, her touch extremely gentle.
I reached to her as well, trying to unbutton her blouse and gain the same access, but she stiffened up and reached out a hand to stop me. Before I could say anything, she leaned forward and began licking first my left nipple, then my right. Not sucking, but gently licking. It wasn’t the kind of rough treatment I love so much on my tits, but it was unexpectedly nice. We both heard footsteps approaching, so she pulled away, I re-dressed myself, and we left the room, saying our goodbyes.
Back in my room later, you and I talked, and as I told you about Jen, you asked me to get out my toy and push it all the way inside my tight, wet pussy. Overwhelmed by the sound of your voice, my encounter with Jen, and your suggestions that I pursue more naughtiness with all these new friends, I brought myself to a fast, powerful orgasm. I told you I love you, and we said good night.
And that brings us to Thursday. During the day, as you were at work and I was in my conference meetings, we had several conversations in which you challenged me to make the most of my encounters, and be the slut you knew I could be, getting you a picture of Jen’s tits and sucking John’s cock - and whatever else…
Luckily, between workshop sessions, I managed to figure out where both Jen and John’s apartments were within our complex of student housing, and invited myself over to see each of them, back to back, on Thursday evening. And when I say ‘luckily’, I mean that my desire to please you was so strong that I made damn sure it happened.
During dinner with my colleagues at the campus pub that evening, I was practically drooling over a sexy red-headed waitress, so much was I anticipating my evening to come. We finished our meal, returned to our rooms, and I pretended to settle in for the night, waiting for my opportunity to leave my room without anyone noticing. Just as I was about to do so, a fire alarm went off in a nearby building, and I watched and waited as evacuees gathered outside, the fire truck arrived, and the minutes passed. I was still filled with anticipation, but now also with anxiety, that perhaps one or both of my encounters wouldn’t happen!
As soon as the commotion in the courtyard outside our buildings had passed, I left as quickly as possible, arriving at Jen’s building by about 10:15. I knocked on the door, she welcomed me in within full view of her colleague/roommate, and invited me into her room to “continue our conversation” from earlier in the day. Amazing, I realized, how two women can pretend to be ‘just talking’ when truly they have much different intentions.
We went into her room, shut the door, and she immediately reached to pull out my tits and began touching them. This time around, I encouraged her to be rougher, instructing her in how much pressure she could use in grabbing my full breast and squeezing it, or in pinching my nipples between her long, delicate fingers. She licked and sucked and pinched and twisted my nipples, and whispered her amazement at how much pressure I could take.
This time, she also let me touch her. She was much more sensitive, but I pushed her boundaries a bit, nibbling and pinching her nipples more than she seemed accustomed to. I asked if I could take a picture of her perfect tits, and explained that the picture was for you, and as soon as I promised that I wouldn’t capture her face, she was excited by the idea. She quickly pulled off her shirt and bra and posed for me.
Once I had that picture for you, I helped her out of the rest of her clothes - shorts and panties, and she laid back on her bed, naked, and got a toy out of her dresser and handed it to me. She was clearly inviting me to pleasure her, but didn’t have any concept of how to make that happen except with her toy. I took one more picture for you, but then put my phone down so that I could give her all of my attention.
I turned on the vibrator and rubbed it against her clit and wet pussy for a few moments, but I soon set it aside in favor of using my fingers and tongue. She did nothing to stop me, her dripping wet pussy completely exposed as she spread her legs wide for me. Her pussy lips were pink and dainty and everything was completely shaved. I licked and sucked her clit as I explored her incredibly tight pussy with my fingers.
Jen came twice as I licked, and sucked, and rubbed, and fingered her. This was a first for me, going down on a woman, and it was amazing. I was covered with her juices and she tasted absolutely delicious. I could feel her every moan and shudder as I kept licking and finger-fucking her, and my clit was throbbing the entire time.
We then reversed positions, with me lying on the bed and her kneeling between my legs, spreading them wide, and giving my pussy the same attention I had given hers. I didn’t last long with her gentle tongue licking in slow strokes from my pussy to my clit, and her gentle fingers probing my wet hole.
As I panted and recovered and the room stopped spinning from my powerful orgasm, Jen climbed on top of me and we attempted a 69 position. With the ridiculously small dorm bed positioned up against a wall which we both banged into, undoubtedly waking her roommates, we gave up on making it work, collapsing into giggles. We got dressed and I said my goodbyes, my clit still throbbing and her taste still in my mouth as I moved on to John’s building.
I was much later in getting to John’s than I had said I would be, and he was obviously waiting nervously by the door, because he answered almost instantly after I knocked gently. He pulled me quickly into his room, clearly nervous that any of his roommates would see or hear. Once we were in the room and the door was closed, he put his finger to his lips, driving the point home that I should be as quiet as possible.
He immediately pulled out my tits and began playing with them, and I encouraged him to be rough, even though I knew I would be a bit sore from two people going to town on my nipples in the same evening. Luckily, it was nothing compared to the treatment you’ve given them in the past - I’ve developed some real stamina when it comes to having my tits abused.
After a few minutes, he sat down on the bed, I pulled off his boxers, and I got down on my knees between his legs. He was already hard, and I was impressed with the size of his cock. He wasn’t long, probably 5 inches, but he was very thick. I could only make my fingers meet when wrapping them around him if I squeezed, hard. His balls were huge and hairy. I remember thinking how these two encounters couldn’t be more different - Jen’s soft skin and tight little pussy, and now John’s thick cock and hairy balls.
I began the blowjob slowly, cupping his balls and gradually taking his thick cock into my mouth. I asked if he would take my picture while sucking his cock, and his nervousness from the car the morning prior returned. Under no circumstances was he going to let me have a picture which included any part of his anatomy. Fine, I agreed, and went back to work, still hopeful that I could convince him once I had him closer to climax.
After a few minutes, he began tugging at my pants, and I took the hint, standing up to remove them, my panties, and then his shirt. I was still wearing my shirt and bra, although both were shoved aside to give him plenty of access. He laid down on the bed and pulled me on top of him into a 69, much more successfully than my earlier attempt with Jen. I got the sense he’d done this before, perhaps with Whitney?
I went back to work on his cock, sucking and stroking, struggling to keep my focus as he began licking me. His tongue was stronger and rougher than Jen’s, which was a huge turn-on. First he licked my clit and thrust two fingers inside of me. Then, he grabbed me by the hips and pulled me down firmly onto his mouth, fucking me with his tongue. I came very quickly, still stroking and sucking him as I did, although without any rational tempo, I’m sure. I don’t know how I found the ability to remain quiet, remembering my surroundings, because I wanted to scream, my orgasm was so powerful.
After I recovered, I turned around so that I could face him, as it seemed an easier position to continue sucking him. The whole blow job, I’m guessing, lasted about 15 minutes. Nothing compared to the workouts you’ve given me, but still very impressive compared to many of my other encounters with strange new cocks. I once again reached for my phone and asked if he would at least take a picture of me, even without him in it.
I told him that I wanted him to cover my face and tits with cum, and capture pictures of that for me. He instantly agreed, and I could tell that the suggestion brought him closer to climax. My goal was to catch what I could in my mouth, so that I could taste him, and then quickly pull away so that I would still be covered for you to see.
After another minute or so of fast stroking and bobbing up and down on his cock, I could feel that he was ready. His cum was salty, but fortunately plentiful, and I was able to accomplish my goal, swallowing the first bit of it and then pulling away, keeping my grip on his cock so that I was able to control where his load hit me. The majority hit my glasses, while the rest trickled down my tits. I took my phone back from him once he was done, making sure that he’d taken the pictures I’d asked him to.
He was perfectly nice about it, but it did seem as if he hurried me out of his room - I’m guessing he either had plans to see Whitney, or was still nervous about being caught - but either way, I dressed very quickly, and was soon walking back to my room with cum still dripping from my glasses and down my chest.
Even though I had already cum twice, once with a woman and once with a man, I was still so turned on by all of my activities that I knew I’d have to bring myself to orgasm one last time once I was back in my room. I stripped off my clothes, got my toy, laid down, and worked as slowly as I could given my excitement, so as to prolong the outcome and make it as satisfying as possible.
And that brings our story back to where it began.
“Are you awake, yet?”
I love being your slut. I love telling you stories about the naughty things I have done. I love how much I trust you, and how much you challenge me.