Gap Year Experience Pt. 03

(This follows on from Gap Year Experience Pt. 02, so might be worth your reading that before reading this)

Following that first "date" after our tennis match I returned home as Andrew had another engagement that afternoon.

He was also busy on Sunday so the next time I saw him was at work. As he was a fairly senior figure, in overall charge of our sponsorship programme, I didn't get any real chance to spend time alone with him, and our interactions were entirely professional, giving no hint to any observer that we knew each other any more than any of the other students. I imagine this was by design as, presumably, he was violating all sorts of corporate rules by having sexual relations with one of the students - male or female.

In fact with hindsight the whole thing was somewhat morally dubious, but I genuinely didn't even think about that at the time, I didn't feel coerced and I certainly didn't think that there was any link between my job and career progression and my relationship with Andrew. (Later in my academic, and indeed professional, career I would go on to have sex with authority figures for much more mercenary reasons, but that is another story and we are jumping ahead...).

I was, sexually, extremely frustrated, having been given my first taste of actual real live sex for the first time, I wanted it more and more. I confess that I masturbated incessantly that week, reliving the experience of the previous Saturday.

I would imagine what Andrew might do to me by way of punishment, and I have to say that I was even a bit surprised at how far some of my ideas went!

I experimented with whipping myself with a belt, and also used a candle as an improvised dildo in my arse, imagining Andrew's strong cock forcing its way in there. Violating me.

On Friday after having no meaningful contact with Andrew all week I found a typewritten note in my messages folder (this was pre internet) that simply said "Tennis tomorrow? Meet at my house. No need to bring a racquet." The note was unsigned - anonymous and deniable - but there was no doubt who it was from. I immediately felt butterflies in my stomach and a rush of blood to my cock.

The "no need to bring a racquet" made me smile. Clearly he was signalling to me that there wasn't going to be very much, if any, actual tennis involved tomorrow, but could equally be interpreted, to anyone else, innocently, as his willingness to lend me a racquet.

I was excited that night, but also nervous. Unusually, I didn't masturbate, saving myself for the next day.

I arrived at his house the following lunch time, dressed in my tennis gear, as required for a tennis date. I knocked at the door and Andrew answered, dressed in casual slacks and an open neck shirt "Good morning" he smiled. "Come in."

His house was very normal. Quite old. Some heavy exposed beams. No sign of "gay taste". Several bookshelves, but nothing out of the ordinary, and certainly nothing sexual on display. One of the bookcases was locked and I was later to learn that it contained quite a collection of erotic literature, "artistic" photographic books by the likes of Robert Mapplethorpe (of whom I had not, at that point, ever heard) and straightforward pornography much of it focussed on young men (of, I am pleased to report, respectable and legal age) being dominated by older ones.

He served a simple lunch of fish and salad, accompanied by a glass or two of white wine. I suspect, with hindsight, that the wine was pretty average, but at the time I thought it delicious, and very sophisticated.

We chatted about generalities before the conversation inevitably came around to sex. He asked me about my fantasies; what I usually fantasised about when I masturbated. I was pretty taken aback, but he persisted "For example, which actors or actresses do you fancy?"

I confessed to having a crush on a few famous actresses, including a couple of the classic English upper middle class type, one American and one Australian. Also, appropriately, a couple of female tennis players.

"What about actors?"

"No not really. It has never really occurred to me."

He looked slightly disappointed.

"What about boys and girls at school?".

Here he was on more fertile ground as I had been at an all boys school and confessed to a few unrequited crushes on class mates, the details of which I will not go into here.

We talked about the other students on my current course. Which of the guys we thought might be gay or bi. We agreed that one in particular, a studious slightly nerdy, but quite cute, guy called Timothy was a likely candidate.

He assured me that I was the best looking guy on the course, and that most of the girls and some of the guys would be masturbating about me each night. I didn't really believe it, but it turned me on to hear it.

I had certainly given a lot more thought to the guys on the course over the past week since Andrew had first seduced me. I had started to look at the guys in a new, sexual, light. I was doing a certain amout of "crotch-watching" and mentally undressing some of them.

There were two I found quite attractive. One was cool, dark and brooding looking. I thought he was sexy, but he had already seduced and paired-off with one of the girls on the course, so I didn't think there was much opportunity there.

Timothy, on the other hand, had not appeared to show any interest in the girls, or vice versa, and I had started to entertain the possibility - encouraged by discussion with Andrew - that he might be gay or at least bi. I had fantasised about being in bed with him a number of times, and the things we might do in that situation. But in reality I had to confess that the person I had fantasised about most over the past week was Andrew, to which he responded "Good, that is very good."

(As an aside, readers might think that somehow Andrew was "bad" for turning an impressionable 19 year old "gay". I don't think like that at all. Apart from disagreeing with the basic premise that it is somehow "bad" to be gay, Andrew didn't turn me gay. He was just the first person who offered me an outlet for a part of my sexuality that had always been there, and indeed always would be there. I am grateful for that because it opened up many amazing experiences, with some amazing men (and some bastards too!) over the years. I wonder how many of these I would have missed if Andrew hadn't taken the initiative to seduce me, so for that I will always be grateful).

After a while of this sort of flirtatious chitchat he suddenly said "Although you look very sexy in your tennis gear, I'd like you to take it off now."

I wasn't quite sure I had heard correctly as it seemed to be a bit of a non sequitur.

"I am sorry?"

"I said you can take off your tennis gear. As I am sure you can guess we aren't actually going to be playing tennis today."

"No but..."

"So you don't need to wear your tennis clothes. Whilst you are here I want you naked."

"What?"

"Or you can go home now. I want you naked so I can enjoy your body. But if you don't want to you don't have to stay."

I was slightly shocked at this idea, but immensely turned on.

" Ok." I said, rather hesitantly, and began, equally hesitantly to take off my shirt, tennis shoes and shorts.

I stopped and looked at him questioningly, as I stood there in my underpants.

"Yes, those too. Your body needs no adornment and I want to be able to see it. The house is very private and no one will see you except me."

It was an odd situation. I didn't really imagine that anyone would have any reason to find me physically attractive, so when someone, a sort of authority figure, tells me he wants me naked so he can admire my beautiful body it is a bit of a head fuck. I removed my underpants and stood there naked for him to examine me.

He sat in an upright kitchen chair.

"Come here."

I walked over to him. My naked cock was approximately at his eye level. He reached round to grasp my buttocks and pulled them apart. In the same motion he pulled my crotch close into his face.

"Gorgeous. A lovely cock. Lucky me that I get to play with it. "

He then made me turn around and bend over so he could admire my arse.

"Touch your toes."

I bent over to touch my toes, exposing my arse to his gaze - and his touch.

He ran his hands over my cheeks, and his fingernail down my crack. He poked at my sphincter. "You could - and probably will - make a lot of men very happy with this arse."

"By the way, you know I am going to fuck you today?" he said casually.

For the first time. I was actually terrified by the idea of his huge cock forcing its way inside me.

"How do you feel about that?"

"Uh, I don't know. Wouldn't it hurt?"

"Haha, yes, probably. At least the first time. But once you get used to it it feels amazing."

He caressed my ass again. Then kissed the cheeks. He pulled them apart, and ran his tongue along the crack, further teasing my anal bud, but now with his tongue.

Then he paused and said "But you also know I am going to punish you first. Do you want that?"

I didn't quite know what to say. Part of me was screaming "Yes, yes, yes!" but the reserved conventional side of me was unable to admit this.

I said "What sort of punishment?"

"Oh, it depends."

"Depends on what?"

"On how I feel, and what I think you would like."

"On what I would like?" I was surprised.

"Yes. I never punish anyone who doesn't want to be punished. That would just be assault!" He smiled.

"Let me explain. I enjoy punishing sexy young men. That is I enjoy punishing sexy young men who want to be punished."

"But who wants to be punished?" I replied.

I realised I was being deliberately obtuse here as, deep down, I knew who wanted to be punished. I was one of those people. But the alternative was to admit it publicly, and I wasn't ready to do that. I recalled being caned at school once and I was alarmed to have some quite disturbingly erotic thoughts at the time, involving the headmaster who administered the caning. However I had pushed these way to the back of my mental cupboard as something I did not want to deal with.

This was different. I was an adult and I was embarking on a journey of sexual exploration and I wanted to know where it was going to take me. I wasn't yet ready to admit to Andrew (or anyone else) that I wanted to be punished, but I wanted him to draw it out of me, or even better, forcibly punish me without my having to admit I wanted it. Do I sound complicated? It is a miracle that I ever get laid at all...

"Oh, lots of people like to be punished. I insist that in a relationship with me, my lover must accept regular punishment. I have a dominant nature and I like sexually submissive young men."

I heard "relationship", "lover", "punishment", "submissive" and my cock started to swell.

"But how do you insist? Isn't that just assault if you don't give them a choice?"

"Oh they do have a choice. They can leave. I just told you to take your clothes off. I didn't offer you a choice, but of course you had one. You could just have said "no". You could have left. You are a strong young man. I couldn't stop you leaving and I think I would have a tough time forcibly undressing you" he smiled at the notion. "You chose to stay here and you chose to undress. Is that correct?"

I nodded in assent - it was hard to argue when couched in those terms. He had "made" me undress, but in reality I had chosen to undress.

"How would you punish me?"

"Well it would depend. I could spank you with my hand on your bare bottom. I might then progress to the belt or the cane. Or maybe, if I am feeling a bit adventurous,I might use the tawse or the flogger."

I had never even heard of a tawse, but I didn't admit that.

"Would it hurt?"

He laughed again.

"Well yes, punishments are meant to hurt. Of course there are many different degrees of pain depending on the punishment. I mean a spanking", at which he slapped my bare arse with his hand "can be quite playful, whereas the cane, if used really hard, can be indescribably painful. The trick for me is to inflict the right amount of pain for you."

As he spoke my perfidious cock betrayed me and gradually sprang to attention. It was exquisitely embarrassing to be naked as it was so obvious when I was turned on.

Obviously he noticed this and said "So you like the idea of being caned? You don't need to answer" he laughed "your cock is telling me loud and clear" he laughed again, spinning me round and sitting me down on his spread knees.

He kissed me, and gave my cock a squeeze "shall we proceed?"

I nodded, silently. Not looking him in the eye.

"Good. Stand up and follow me." He took me by the hand and led me through to the living room.

In the middle of the room was an old, leather, chesterfield sofa.

"Bend over the back of the sofa".

I hesitated and then walked to the sofa and bent over to rest across its back. Head down, hands on the cushion. Hips across the backrest, my erect cock pressing into the hard shiny leather of the back of the sofa.

"Legs apart" he demanded, and I opened my legs, spreading my feet a couple of feet apart. I was completely exposed.

Initially he gave me a few hard spanks with his hand, alternating between each cheek. They hurt, but really this was just a warm up. It got the blood flowing and my arse started to feel warm and sexy.

Then he started to up the ante, and spanked harder and harder. This now really hurt. Also, with each spank, my cock was driven against the back of the sofa, adding additional stimulation to what was already sensory overload.

He paused. "I see you have worked up a nice colour! How does it feel?"

I couldn't really answer.

"Let me guess. It hurts, but your arse is starting to feel warm and it is making you horny. You don't want me to spank you again, but at the same time you do."

I nodded. he was right. That was exactly how I felt.

"Well I am going to stop now"

I realised that I felt a pang of disappointment.

"But your punishment isn't over."

He then removed the belt from his trousers and wound it around his hand at the buckle end, leaving a couple of feet of supple leather hanging free. He swung it into my line of vison and then slapped the belt gently onto my back, and let it run gradually down my spine towards my buttocks. He then grasped it near the tip and traced the end down my ass crack, over my anus and down to my scrotum. He gave my balls a couple of gentle taps which, despite their gentleness, were quite painful.

He was emphasising my vulnerability and the power he had over me by his ability to inflict great pain with minimal effort. I received the message loud and clear, and my cock strained further against the leather of the sofa. Exquisitely aware of my submission.

Then he took a step back and started to flog me. Gently at first, warming me up further. Depite their gentleness the strokes still hurt, and caused a sharp intake of breath as each stroke impacted my naked cheeks. He gradually increased the force in each strike, and the leather bit into my flesh. Now it really hurt. I started to wonder whether I was going to be able to take this, but after the first 10 or so strokes the pain sort of plateaued. It was odd because he was hitting me harder, but as my arse warmed up more and more the pain no longer mattered so much. It still hurt - a lot - the final 10 strokes were really quite brutal, and I had to grit my teeth to maintain my composure and deal with the pain, but it was less than I imagined.

Finally he stopped and I was left breathing heavily, relieved that the pain had finished, but feeling the throbbing in my buttocks as the blood pulsed through my tortured flesh.

He put his hands on my cheeks and carressed them. " How was that? " he asked "How did that feel?"

I couldn't really speak, so he continued

"You mark up nicely" he said, appraising my arse like a piece of meat.

He stroked and massaged my buttocks and then squatted behind me to take a closer look. He kissed my cheeks and then pulled them apart and kissed my arsehole.

"I think we might apply a little lubricant just here" he touched my anus "what do you think?".

I still could barely speak. " What for?" I croaked.

"Oh, just in case...."

He disappeared for a moment and came back. I could hear the click of a plastic bottle or tube being opened and then I winced as I felt cold slimy lubricant squeezed on to my anus. I felt his strong fingers massaging it in and around my anal bud, and then I gasped and clenched as he slipped a finger inside.

He started to massage me internally, in what I later learnt was a prostate massage, this actually felt good and I started to relax and to grind my hips a little and push back onto his finger to enhance the sensation.

Then to my dismay he abruptly withdrew his finger and casually wiped it clean in the crease between the top of my inner thigh and my perineum.

"Right, now time for the real punishment" he said.

"What do you mean"I gasped "haven't you done that already?"

"Oh no. That was just the warm-up. Now it is time for the cane. A proper punishment instrument"

As I have mentioned previously I had been caned once before, at school and that, I recalled, hurt like hell. And I had been fully clothed. Now I was naked and bent over the back of a sofa.

He was obviously experienced in this, as he said "Now, we need to adjust your positioning here. You are going to need a bit more padding on your bottom to take the cane properly. He carefully adjusted me so that my legs were a bit more stretched out, and less bent at the hips. It is a little hard to describe, but this had the effect of reducing the extent to which my buttocks were stretched over my hip and pelvic bones, so now there was more flesh there to absorb the impact of the cane.

He again stepped away briefly and returned swishing something through the air. He came around to the front of the sofa...and showed me the cane. To be honest it wasn't really a cane. It was more like a piece of wooden dowel rod, about 5mm in diameter and about 75cm long. So it was light weight and quite whippy. He slapped his hand with it a few times, and then whipped the arm of the sofa hard to demonstrate its power. I shuddered as I saw the way it thudded into the leather of the sofa, leaving a distinct mark where it impacted. I couldn't quite imagine what that would be like on my arse - except that it would be bad!

I also noted that, although he was still fully clothed, he had unzipped his trousers to release his cock. Judging by its semi tumescent state, presumably a result of his whipping me, it was probably getting uncomfortably constrained inside his trousers.

He disappeared around the other side of the sofa and then l felt the tip of the cane tracing the familiar path down my back to my arse. Then down my arse crack to my anus, where it stopped. I then felt pressure against my sphincter as he pushed the tip against it. My well-lubed anus opened to receive the wooden implement and he slid it an inch or so inside. I flinched and squirmed at the intrusion, not knowing how far he planned to insert it.

He chuckled "I think it likes you" and pushed it in and out, not going further than an inch or two each time, but enough to make clear to me, once again, just how vulnerable I was.

Then finally he withdrew. "Enough of this. Time for your punishment. I am going to give you thirty more strokes. But you must ask me for each one, and you must thank me after each one. And you must address me as sir."

I realised that he was living out some schoolmaster fantasy, and as that chimed with mine I was aroused by the idea.

The first stroke was relatively gentle, but still much more painful than the belt. Then the next was harder and the third harder still. I really thought I wasn't going to be able to cope with the pain. He struck harder and harder. Always controlled, and always making me ask for the next stroke before he struck. This was some kind of perverse mind-fuck in the sense that it was a sure way of gaining "consent" for each stroke, but it also added an extra kick for him to hear me asking for the pain.