tagFirst TimeShaving Rupert

Shaving Rupert


Rupert intrigued me. Unlike most boys of his age, he seemed more comfortable in the company of girls than the company of his male contemporaries. I and the other girl's didn't mind, he was every girl's older and wiser brother. We could rely upon him for an honest opinion of our clothes, our makeup, and hairstyles. He never criticised, just made positive suggestions about changing this or that, a different colour better for my complexion.

We'd been close since childhood, we walked home together when at school, he'd stop off at my house to play games when we were younger and later to talk about our hopes and fears, life, love and the universe. He displayed effeminate characteristics, his mannerisms girlish rather than manly. I remember when he started shaving how upset he was to lose the soft boyish sheen of silken hairs on his cheeks.

The first time he shaved was at my house, the blond hairs on his upper lip and chin had begun to freak him, not enough to shave properly but more than enough to ignore. I sat him on a chair in my bedroom and brought my fathers razor and shaving foam, covered his shirt front with a towel and sprayed foam onto his chin, screaming and jumping back because I pressed the nozzle too long and covered his plump red lips with white foam.

I wiped off the excess and spread what I needed into his chin and across his upper lip. Then taking up the razor I tried to figure out how to shave him. I hiked my dress and straddled him settling my crutch onto his lap barely aware of what I was doing, concentrating on the task before me. Not that it mattered, he'd seen me often enough in my underwear when we tried on clothes if I was going on a big date.

I shaved him delicately, little strokes, shifting my position on his lap to reach where I needed to shave, I slowly became aware of his hands on my hips, it was innocent, he really had nowhere else to put them. That was a mistake; once I was aware of his hands, I became aware that my cunt pressed against his crutch. The shaving quickly became of secondary importance my mind concentrating on what I could feel through my panties. I moved myself several times, always within the context of shaving him, trying to find his dick, slightly concerned that seemed to be no bulge in his jeans for me to press against. I stopped shaving him once I felt the dampness in my panties and caught my musky scent drifting up between the chimney formed by our bodies.

Taking the towel I moved back onto his thighs glancing down to see where his dick was hiding, seeing nothing except a slightly darker patch on the crutch of his jeans where my crutch had been rubbing his. I cleaned his face with the towel fully aware that he if looked down he would see my damp panties, probably see my cunt silhouetted through the fabric.

"There Rupert. Your first shave. How does it feel?"

He rubbed around his chin and upper lip, delicate fingers, touching gently, I had an urge to place them elsewhere, but I wasn't even sure that he realised what I'd been doing.

"It's great Lena, you did a really good job."

"All part of the service." I said swinging my leg off him, actually showing him how wet I was but he didn't look, just twitched his nose as if he'd suddenly caught my perfume.

To be honest, I felt a bit of a fool. I loved Rupert dearly, I'd just never thought of him sexually and it was quite clear to me that he didn't think of me sexually at all. Any other boy I went out with was only too keen to squeeze my breast or try to touch enter my knickers. They just didn't understand, patience is all that's required. A trip to the cinema and an attempted grope was not going to win them the prize. It took much more than that and no one had come close. Not with Rupert on my mind.

Shaving Rupert became a regular weekly ritual. I'm still not sure who was getting the most out of our weekly sessions. Rupert seemed to enter some sort of trance once the ritual began and I found myself rubbing against his groin with a lewdness that embarrassed me. Once I even considered not wearing panties, just to see if he'd notice but chickened out at the last minute. Eventually I got to the stage where I looked forward to our weekly sessions with a distracting intensity, only to find that once we assumed our positions I was anxious for him to leave so I could throw myself on my bed and bring the release he denied me.

Once school finished, our weekly shaving sessions stopped. Only in real life; in my fantasy world I shaved every hair on his body working delicately with my imaginary safety razor around his penis and balls, I'd masturbate like crazy and longed for him to return the favour, to shave my cunt, to rub the shaving foam over my slit until I screamed.

I went to university, Rupert went to work for a local patisserie, we saw less and less of one another. I heard rumours that Rupert was homosexual, he'd been seen in the local town in a pub frequented by the gay crowd. I didn't believe it, I know Rupert enjoyed our sessions, I'm sure he got aroused, there were always moments in our sessions when he closed his eyes, lay his head back, breathing short sharp breathes of barely concealed excitement. But that was as far as it went, he seemed content to receive only half of the prize.

One Saturday in late October I sought him out at the patisserie. I hung around until his lunch break and walked with him to the local sandwich bar. We talked about inconsequential things and over lunch I invited him to the Halloween Ball at the student union. He took a lot of persuading but finally agreed. I told him he needed a costume, nothing too fancy just something to match the spirit of the night.

He came to my room at about seven pm. I opened the door, quite deliberately, in my bra and panties. He hid his eyes with mock embarrassment, or so I thought.

"Lena, put some clothes on, were not kid's any more."

"I'm sorry Rupert, am I embarrassing you."

"Well, you not a girl any more, you shouldn't really be walking around in front of me half naked."

"What about completely naked?"

He frowned considering his reply, "I'm not sure that would be right, between us."

I didn't know what to make of that, he seemed to be rejecting me, it only served to increase my resolve.

We put on our costumes. He came to my room on the university campus to change because he didn't want to walk across town in his skeleton body suit. He changed in the bathroom, much to my growing annoyance.

During the evening he stayed by my side, danced with me, talked little with my friends, didn't object when some other drunken geek danced and mauled at me. He was a disappointing date, I felt he'd rather be somewhere else. We walked back to my room trailing our feet in the dew-laden grass, taking the short cut.

"You didn't enjoy yourself." I said.

"It's not really my scene. I feel out of place with the student crowd, they're too boisterous."

"So what would you prefer?"

"Tonight, Halloween night? I'd rather be on a mountain top under a full moon and let the spirits of Halloween enter my soul."

"That's a strange thing to say."

"Why? Halloween is supposed to be when strange things happen, when you let yourself be taken over, when you do wild things with the excuse that it is the 'spirits' making you do it. That Halloween Ball was just another excuse to get pissed and grope a few girls."

"Tell me about it! I'm sure my bums bruised. Why didn't you come to my rescue?"

"Did you want me to? You seemed to be enjoying yourself."

"You're hopeless. You were supposed to be my date. You're supposed to protect me from getting mauled not just sit on the sidelines."

"I preferred to watch you. I like watching you."

"You didn't like watching me when I was in my bra and panties."

"Ah... that's different."

"How so?"

"It was blatant, too obvious, not like when you used to shave me."

I gasped and felt myself blush.

"What do you mean?"

"When you used to shave me, you became a different person, possessed in a sense, like a spirit had control of your body. You were not a girl, you were a woman taking her pleasure while I sat before you."

Now I really blushed.

"I... I didn't think you noticed."

"Hemm... Why would you imagine that? Your movements were quite explicit. Even that first time you let the sensations control you, I could smell the sweet muskiness of you, I can still almost taste that smell."

Jesus, does he know what he's saying, he's going to smell it again in a moment if he carries on talking like that.

"But you never reacted, you never showed that you noticed."

"Oh, I reacted Lena."

"Then why didn't you..."

"Screw you? Why? You clearly enjoyed what you were doing and it gave me pleasure, why spoil a good thing. I miss those sessions, they were the highlight of my week."

"Mine too."

I closed the door to my room and leant back against it, looking at Rupert standing there in his skeleton costume and eventually laughing at the ridiculousness of the situation.

"What's so funny?"

"Well you in that costume for a start and the thought that we spent six months getting each other off without the other realising. Can I get you anything?"

"Such as?"



"Tea, beer."


"Is there anything you would like?"

"I'd like to play a game."

"What sort of game?"

"A Halloween game, a game of fantasy."

"How do we play this game?"

"You have to imagine the wildest thing that you want to do. You have to imagine it's not you that is doing it, but you are being controlled by spirits. You have to let yourself go completely and let your inner spirit control the things that you want to do."

"I've never heard of this game. How do we start?"

He turned around, reached into his rucksack and handed me a razor and some shaving foam.

This time I didn't wear panties, I didn't wear anything. I sat him on the chair and removed his skeleton body suit; his penis lay stubby and tumescent against his thigh. I sprayed foam onto my hand and worked it around his penis, touching it for the first time, feeling a tingle in my nipples that gently effused down across my stomach searching for greater sensation. I shaved him carefully concentrating on not nicking him holding his penis clear from his body to make room for the razor, feeling it pulse, its heat.

I wiped him clean with the towel and looked up at his eyes as I lowered my mouth toward the tip of his penis poking my tongue just to touch the head, feeling him jump at that first caress. Then becoming bolder I edged forward letting the bulbous head kiss my lips, tasting for the first time the salty leak at the tip. He sighed edged forward pushing gently at my mouth, showing me what he desired. My nervousness evaporated, other sensations took over as I opened my mouth and let him enter me. Not far, not too much, enough to moisten and excite, I wanted this elsewhere.

His hands held my hips, just like before, I straddled his crutch and lowered myself gently onto the wetted head of his penis. I used my fingers to open myself, not really certain how to do this but knowing it must fit in there and slowly eased him inside me wincing as his penis burst through, then feeling the pain pass to heat, and the heat pass to desire, and desire pass to lust as I sank down upon him and rested breasts against his chest, while my cunt felt the measure of him.

I insisted I shave his face while we gently fucked, both of us for the first time. I don't know how many times I came, for a time it seemed that I came with each stroke of his penis, with each stroke of the razor. We stayed for as long as we both could bear it, his erection keeping me pinned in place until finally he subsided and only our secretions bound our bodies. He never touched my body, not then, his hands never moved from my hips that first time. He said it was my fantasy, for me to act out.

Later in the night, he shaved my cunt and took me like a demon driving himself into me, shifting me bodily on the mattress with his thrusts, living out his fantasy, commanding my body to respond and I came with a series of convulsive spasms as he spilled the heat of his body into me.

In the morning, Rupert reverted to his former gentle self, his demon spirits vanquished with the dawn. Now we make love at our own pace, for our mutual pleasure, and even now, once a week he places a chair in the middle of the room and hands me the shaving foam and the razor.

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