It was my first term at Oxford University and I was enjoying my freedom - the ability to wear what I liked when I liked and to have friends visit me without getting my parents' permission first. I had been wearing women's panties in secret under my male outerwear for nearly two years but keeping it a secret from my parents, not to mention the washing and drying, had been very stressful. Now independent, I was able to enjoy my transvestism. I started wearing feminine outer garments too - slacks and blouses; not too feminine but enough that I attracted those of similar inclinations.

I well remember the first personal tutorial with Dr Roberts at which I wore nothing but feminine clothes. I was wearing lightweight smooth womens slacks with the fly fastening the women's way and a women's polo necked top which was almost long enough to conceal the feminine fly on the slacks. However, it wasn't long enough for Dr Roberts as he introduced the tutorial with,
"One thing we welcome here at Newton College is diversity, whether in intellectual pursuits, behaviour, personality or sexual inclinations. I've had a feeling that you had a softer, feminine side, and I rather like that in a student."
(I must mention that Newton was an all male College at the time) Despite his reassuring tone and the words he had just spoken, I blushed and muttered something like,
"I try to be the person I am but it's not always easy".
"Don't worry about it John; these tutorials are confidential and anything said or done here will go no further."
The tutorial then moved on to more academic lines but that somewhat embarrassing beginning had me thinking.

Next time I visited Dr Roberts in his rooms, I wore the same slacks as before but this time a very feminine silky blouse replaced the almost unisex polo of my previous tutorial. Dr Roberts was obviously pleased with my appearance as he complimented me with,
"Good to see you looking so smart, John, and wearing what you're most comfortable in. I must say that blouse really suits you and it goes well with the slacks."
"Thankyou sir." was my reply. This time I still turned a little pinker than usual but my blush was minor compared with last time. Dr Roberts invited me to join him on the sofa rather than sitting facing him " ... as we can both go over your essay together if we're sitting side by side" was his reasoning. After a discussion on the merits and failings of my essay writing Dr Roberts got up to brew some coffee but as he did so he put his hand on my knee and then said,
"Oh, sorry my dear!" as if the physical contact had been an accident.
"That's all right", I replied. Indeed the feel of his hand on my lower thigh hadn't been just a touch, more of a brief caress which I must admit I had rather enjoyed. I wasn't sure how to encourage him - assuming the caress had been deliberate - but Dr Roberts soon solved that problem.
"I couldn't help noticing what a nice smooth feel those slacks have"
"Yes, sir. That's one of the things I like about women's clothes; many of them are so much softer, smoother and silkier on the skin than menswear. He returned to my side and this time, obviously relieved by my positive response, he deliberately stroked my thigh through my slacks. At this I developed an erection which, because my slacks and the french knickers underneath were of such thin material, was visually obvious to Dr Roberts who said,
"I see that you enjoy being caressed through your slacks!"
"Yes sir. You have a very gentle touch and it is very pleasant."
At this his hand moved higher and started stroking my balls and my erection which now grew to its very respectable maximum.
"I too enjoy being caressed", Dr Roberts said, "but these trousers are too thick. Would you mind if I took them off?"
"No sir. I'd like to see you in your underwear." I couldn't believe what I'd said - it had just slipped out that way.

Dr Roberts then stood up and removed his trousers to reveal his thigh length tight white lycra underpants whose stretchy material was holding down an erection even larger than mine and, having made that earlier remark, I decided to go all the way so when he sat down again, I reached over and stroked him through his underpants and his erection pulsed as I touched it. I was now in a state where I wanted that erection; I wanted to feel it inside me, pulsing as it pumped its seed deep inside me and again I could hardly believe what I was saying as I asked,
"Would you like me to remove my slacks too, sir?"
"That would be very nice" was Dr Roberts reply and as I stood up and took off my slacks, my loose fitting pale pink silky panties with lace trim came into view.
"My, you really DO like girly things, don't you" was Dr.Roberts reaction and before I could sit down again he had stood up behind me and was pressing his crotch against my bottom. His desire was now obvious and again I was amazed at my boldness as I said,
"Yes sir, I like everything about being feminine and I'd like a boyfriend to make love to me."
"Would it be acceptable if that boyfriend was a much older man who finds your young slim feminine body extremely arousing?"
"Oh yes sir, that would be great!"
At this he stopped rubbing his erection against my panty-clad bottom as he stepped back, removed his underpants and got a tube of lubricant from a desk drawer.
"Is this your first time?", he asked, knowing full well that it was.
"Yes sir, so please be gentle with me."
Dr Roberts squeezed some gel onto his erection, now standing proud, and also applied some to my anus after raising one leg of my panties to reveal my intimate hole. He slipped his gel-coated finger right through that ring of muscle ensuring it was well lubricated. Still holding the panty leg clear with one hand, he used to other to guide the tip of his moist penis to my puckered and glistening rosette. The feel as his penis touched my anus was almost like an electric shock and my desire for it to be inside me grew even stronger. He then started to push gently and told me to push as if I was about to empty my bowels. This distended my anus and prepared it to open which it did slowly but surely as Dr Roberts' penis gently pushed its urgent way in. Although there was a little discomfort as my anus was stretched beyond it normal open size, the feeling as that long engorged shaft slid inside me was indescribable. He held still for a good 20 seconds to allow me to get used to his presence and then he slowly withdrew until I felt the back of his glans against the inside of my anus. A gentle thrust followed as he slid all the way in until his balls were touching my perineum. Regular withdrawal and thrust followed in a gradually accelerating rhythm until with a long "oooooh" I felt his penis jerk and spurt its huge load of semen deep inside my arse. He started to withdraw but I begged, "Don't pull out yet!". He was softening by now so I alternately tightened and relaxed my anal sphincter, squeezing and then letting go at the base of his cock which soon hardened again with this treatment.

"I need to pee." were the next words that Dr Roberts spoke, but I didn't want the wonderful feeling of a stiff cock up my arse to go away and I rashly told him,
"If you've got to pee, do it now - inside me."
It took a few seconds for the idea to hit home and for Dr Roberts to relax enough to let his bladder contents start to flow though his still stiff cock and deep into my bowels. It was a lovely feeling as the urine gushed into me, bouncing off the walls of my rectum as it gradually filled that welcoming void. After another two minutes I again felt his penis go soft and this time I let Dr Roberts pull out and I felt my anus close but not before a little spurt of his urine escaped. I thanked him for his kindness and gentleness and told him that I was very much looking forward to our next tutorial. I put my slacks back on and walked back to my room with my new experience fresh in my mind. I was so enjoying the feeling of fullness in my rectum that I didn't realise quite how urgent were the signals from my bowels indicating a need to empty. It was as I unlocked the door to my rooms that a spasm hit me and I felt a spurt of urine emerge from my arse. It soaked my panties and slacks and I made a dash for the bathroom. I got to the toilet just in time before the dam burst, but not in time to lower my slacks and panties. I sat on toilet fully clothed and felt a warm flood envelope my crotch as Dr Roberts' pee poured from my rectum. At this point I myself felt a need to pee and as the panties and slacks needed washing anyway, I just opened the floodgates and let my own bladder empty into my pink panties and silky slacks. This had been a morning to remember!