The Journey - Chapter 7... The Stocking Challenge

So where did I leave you in Chapter Six?

Oh yes, I was opening the envelope to see how I’d be getting fucked after my “Stocking Challenge”.

And what did it say.................. Pussy!
(I actually don’t like that term particularly, but that’s what it said!)

Oh yes, it was about to happen at last, my first full sex with Tom. My heart skipped a beat as it jumped for joy, a huge smile broke out on my face as I looked up at Tom. He already knew what it said so it wasn’t a shock to him, he was just watching, waiting for my reaction.

“Are you ready?” he asked. I stood up from my chair and held out my hand to him so I could lead him to my boudoir, and I said a wholehearted “YES”. I really was ready for this, I had waited long enough, and I’d thought about this moment literally hundreds of times. He took my hand and we headed into my bedroom. I guess you could say it was a little bit awkward, and I guess we were both more than a little nervous, which can be expected.

We sat on the edge of my bed and we kissed. Then we started to undress each other, at this point it was very much like a vanilla sexual encounter. But once my dress and bra was off, leaving me in my thong panties and fishnet stockings, he reached for a small bag he’d brought up with him. He’d come prepared, and pulled out some thin ropes. I was nervous, this was going to be my first D/s sex session, but I trusted him, and knew I’d be okay.

He tied my hands together, and then lifted them above my head and tied them to the bed. My Uni dorm-room standard bed wasn’t ideal, but he somehow made it work anyway, tying the rope around the frame as there was no headboard, and leaving enough rope between that knot and the knot that tied my hands together so I was comfortable. A few weeks earlier when he’d been in my bedroom I noticed him having a good look at the head of my bed, it made sense now, a recon mission! Lol.

Once I was tied to the bed, I was his for the taking, but he didn’t just take me, first he put a blindfold on me, and then he teased me, and teased me, and TEASED ME! He used his fingers, he used my vibrator, he squeezed my breasts and pinched my nipples. I don’t really know how long it was, but it felt like hours. He kept it slow and easy, just keeping me on the edge of cumming but never quite doing enough to make me cum. It wasn’t just unskilled foreplay, he knew EXACTLY what he was doing, he didn’t want me to cum too early. Occasionally he would stop and move around the room, to get a toy or to get something else, and it was an agonising wait for him to come back to me. I couldn’t see what he was doing, so I intently listened, trying to figure it out, only to be surprised when he returned and slipped an ice-cold dildo into me, or poured cold liquid lubricant onto me, or just gently touched me, kissed me, or pinched or nibbled on my nipples when I wasn’t expecting it.

It finally happened though, after a fair bit of pleading from me to be completely honest. “Please! Please, fuck me! I need you to fuck me! Please!” I said continually under heavy breathing. It’s funny how he managed to get me to beg him to let me suck his cock, and now he got me to beg him to fuck me. The subtle ways of the experienced Dom, I guess! Lol

He put the tip of his cock at my entrance and teased me some more, rubbing it up and down, lubricating his rock-hard pulsating cock with my juices before he thrust into me. It felt so good. I wrapped my legs around him to stop him from getting away and teasing me anymore. I needed this, I wanted this, and at that moment, I didn’t want him to be anywhere else other than inside me.

I was still blindfolded, which heightened all my other senses even more, and he fucked me for what seemed like forever. Sometimes gently, and sometimes hard and rough. My hands were tied but I still had fairly free movement as long as my hands remained at the head of the bed, so he started fucking me whilst I was lying on my back, but we soon switched positions and I was on top. Still blindfolded, still in my stockings and heels, bouncing up and down on his glorious cock, having the time of my life. And we finished with him fucking me from behind until he came deep inside me, pulling my hair as he did so. I think I came about 4 times, it was really my first multiple orgasm experience, I didn’t really know it was possible, but it didn’t really matter to me how many official orgasms I had. I was practically in an orgasmic state since the teasing started at the beginning, the whole experience was just so pleasurable.

He untied my hands and took my blindfold off at the end and I lovingly licked and sucked his cock clean before we nestled in each others arms in a tender moment. “You are a fucking God!” I exclaimed to him. He really was, it was the best sex I’d ever had. I’m not sure it still is from a physical perspective, but with what it meant to me at the time, the combination of physical and emotional aspects combined with it being my first time in a D/s scenario, I can probably still say that with some degree of truth that it still is the best sex I’ve ever had.

I guess you’re all wondering if the stocking challenge continued after this, aren’t you? After all, I still had two pairs left unworn, and two holes left unfucked.

Well it did continue over the next few weeks, as did our sexual encounters, we got together for a bit of nookie at least once or twice a week for the rest of the Uni term, which had about 2-3 months left. Our sexual encounters often entailed me being tied or blindfolded, and we experimented a bit with other things too, but keeping in mind that neither of us actually owned any significant bdsm equipment or toys, I couldn’t afford to really buy any on my minimum wage part-time job, and Tom couldn’t go around spending money freely on me with his family responsibilities. So we generally improvised where we could. We even booked a cheap hotel room a few times to get some extra privacy. Sometimes having sex in secret in a shared flat is pretty difficult. Especially as we were trying to keep our relationship secret to all, due to the circumstances – he was older, and married, as I’ve mentioned in previous chapters. I think we did a pretty good job of keeping it on the down low, I think a few suspicions arose a few times with a few people, but we did our best to avoid each other in public sometimes, and deflect the suspicions and rumours. I’d become a bit of an outrageous flirt to be honest, and nobody really thought the older mature student had much of a chance with the popular, somewhat-attractive 19 y.o. blonde. So the rumours ended up being more a tale of unrequited love from him, and me just being too flirty with him. We were happy to keep the rumours that way though.

But getting back to the stockings challenge. It was set again, and I had a choice of two pairs left to wear. I wore the plain black ones with a very sexy little dress. I must have flashed a bit of stocking top several times that day, which would have been a first for me, but it was amazingly fun and I loved doing it, as I was so sexually buzzed waiting for the unveiling of the envelope later that day. I’d given him dozens of blow jobs, so I wasn’t sure how big a deal that one would be, but the anal one would be a new experience and a new challenge.

Upon unveiling the envelope, it wasn’t meant to be at this stage, as it said “MOUTH”. I was quite nonchalant about it, it wasn’t going to be a big deal, but as it turned out, I was wrong. If you remember at the start of the Stocking Challenge, Tom said that the condition was that he’d get to fuck whatever hole corresponded to the choice of stockings. The wording of that is quite important, and I was about to learn that giving a blow job and getting your mouth fucked really aren’t the same thing.

The rope came out again for this encounter, as I knelt down and he tied my hands together behind my back, and then he tied my ankles together, and finally he tied my wrists to my ankles. I really was stuck in this one position. I was quite happy and chirpy, and really wanting to get down to the business of sucking his cock. We soon did, and I started licking and sucking the best I could with no hands. We’d been working on me being able to take more of his length into my mouth – deep throat training if you will. I was nearly there at this point, able to take about 6 of his 8 inches into my mouth and the opening of my throat. And this is how we started, me taking all I could and then moving away. Slowly moving my head back and forth. “You give great blow-jobs” he stated. “But this isn’t about you giving, so much as receiving. Do you trust me?” He asked. I never once took his cock from my mouth, but I looked up at him, gave a slight nod and a “uh-huh” sound.

He then put his hands on the back of my head, intertwined with my hair, and took control of my movements. He was fairly gentle at first, pretty much doing what I’d already been doing, nice slow, deep movements. But he sped up a little bit soon after, and we soon found out that yes, I could take all of his cock, as he pushed every last millimetre into my mouth and down my throat. At the point where my gag reflex begins to kick in, I’d usually stop and withdraw, but the hands on the back of my head stopped me from pulling back, and he firmly carried on pulling my head toward his waiting crotch. The pace gradually quickened, and I wasn’t particularly happy or comfortable at this point, as I continued to gag, and tears began to stream from my eyes, and I was actually quite upset with him. My sounds of disapproval got lost in the shuffle though, and his tight grip on my head, and my hands and feet being tied prevented me from doing anything about it. He’d soon sped up to a rapid pace and was fucking my throat quite furiously, and finally he came in my mouth. As he released my head, I leaned forward and coughed and choked as I tried to get my breath back, and his cum, mixed with saliva and flem came out of my mouth and onto the floor.

Like I said, I was very upset, I really wasn’t expecting what had just happened, I felt used and like the trust I had given Tom had been broken. He tried to be comforting, but as soon as I was untied, I just grabbed my clothes and was out of the door in a flash, dressing whilst walking.

Tom rang me, messaged me, e-mailed me, and tried to speak to me over the next few days, but I ignored him, giving him an icy glare when I saw him in person. I really was quite furious with him. I cried thinking about what happened, but whilst I cried, I’d get very aroused and would end up fucking myself to orgasm.

After a bit of internet research, I found out a bit more about “face-fucking”, and sent Tom an apologetic e-mail for being such a bitch. I really wasn’t upset anymore, it was more the shock about what happened that made me upset, I didn’t realise that people did what he did to people they cared for. But they do, and the more thought I gave it, the more I realised that it wasn’t so bad, I’ll admit I didn’t enjoy the physical act, but I did enjoy the helpless feeling I had, and how hot Tom thought it was, and how raw and physical the looks of pleasure on his face were as he did it. I kind of realised I wanted to give him that pleasure however he wanted it. I explained this to Tom, he explained how sorry he was for putting me in the situation anyway, and we kissed and made up, and we were back on track.

And the best news of all, next time I sucked his cock, I went all the way down with little problem at all. I even started to learn how to hold his cock in that position, without gagging, and lick his balls at the same time. It’s funny really, I was so proud of myself when I did that for the first time, more proud than I’d been of almost anything else in my life. That really is a ridiculous notion, but it is true.

We did re-enact our face fucking scene a few times after that, without me getting upset! It really takes some getting used to, but after that, it isn’t so bad, I promise! In case anybody out there is thinking of doing it! But it is better if you’re expecting it, rather than being naive like I was and it happening completely by surprise.

In mine and Tom’s penultimate ever sexual encounter we even took it to the next level. He set me the challenge of face fucking myself with his cock. He wouldn’t hold my head, he’d just stand there, and I was to treat myself like a slut and put to one side any need to gag or come up for air, and just go to town. It’s quite surreal really, when there isn’t anybody holding your head, forcing you down, to make yourself do it when every inch of you tells you to pull your head back, it’s a tough task. But it went quite well all things considered.

That’s all for this chapter – chapter 8 will continue with the third installment of this “stocking challenge”, plus the culmination of my relationship with Tom.

Until next time! Xx

PS: I’ve had a large volume of e-mails recently, and am doing my best to reply to all, and then reply to the replies, and so on, so please bare with me if I haven’t replied to you yet, or if my responses have been tardy.