Disable your Ad Blocker! Thanks :)
Chapter 8
by
Trom1806
You're tired from this whole period of time studying with Miss Fernandez... Maybe you should stop these extra classes?
You think it's necessary so you don't get expelled from college... So in the following weeks you continue to take extra classes with Ms. Fernandez.
But not everything went as smoothly as miss Fernandez wanted. The problem was that even after masturbating, you could not fully concentrate. The energy was beating out of you, even your vestments in the female image could not completely appease it.
Then Miss Fernandez came up with a new, more advanced method. For the next class, she told you to come an hour early and not eat anything in the morning. A couple of days later, you stood intrigued in front of this mysterious woman, it is not clear why she is showing such great interest in you.
“For this procedure, you will have to undress, so take off your things. I will give you a special massage that will teach you to focus on your feelings.” When I undressed, Miss Fernandez asked me to get on all fours, and she settled herself behind me near my hips.
"Close your eyes and breathe deeply."
With her hands, she began to knead your buttocks, pushing the halves of the ass with her thumbs.
"Don't be scared, now I will put some lotion on your ass."
You felt how her wet fingers began to massage your ass right in the sphincter area. Having thoroughly lubricated this place, she began to caress your anal hole in a circular motion.
“Spread your legs wider. Did you do everything I asked you to do?"
You nodded. Ms. Fernandez gave you clear instructions not to eat in the morning and to go to the bathroom before class.
Meanwhile, her hands moved more and more, sometimes pressing on the place between your testicles and your anus.
“Now I will give you a prostate massage. This is a very useful procedure that helps to be healthy and also very pleasant. We will use it as a way to relax and relieve stress. After all, it is precisely what prevents you from reaching heights in training. After the massage, you will be able to solve the most difficult problems and this will make me very happy.”
Taking a little more lotion on her hand, she actively began to torment your hole, trying to penetrate it with her finger. Instinctively, you tensed your muscles, not letting your finger inside.
“Relax and breathe deeply, that's the only way to enjoy this massage, and that's exactly what we need. Well done, now push a little."
As soon as you tightened the ass, her finger deftly penetrated inside you, causing unusual sensations. You squeezed your ass again, but she did not take her hand away until you relaxed again.
To my shame, the sensation of penetration didn't make you uncomfortable. On the contrary, you enjoyed it. Miss Fernandez began to move her hand and say how good you are, that you agreed and how this massage will positively affect your character. You got used to unusual sensations and enjoyed it.
When you got used to one finger, she added a second finger. Your ass has adapted over time and Miss Fernandez's finger movements have become more rhythmic. When two fingers were already freely passing into your ass, they began to touch some point in the depths of your ass. Touching her was a special pleasure, and you began to wave your ass, trying to improve contact.
“You feel it, right? This place is called the prostate, and for some guys, its stimulation is a special pleasure. Apparently you are one of those. Some even end up without touching their penis, they feel such intense feelings.
From the movement in the ass, you began to gradually go crazy, moaning with pleasure and unknown pleasure. Who would have thought that in such an unusual place there is a source of such acute pleasure.
With her other hand, Miss Fernandez took your little testicles and began to gently massage them. This made your small white cock desperately tense. You so wanted to jerk him off and take the pressure off, but Miss Fernandez wouldn't let you.
You felt that a little more and you will experience an orgasm. At this moment, another penetration hit that very point in your ass, and you started to finish with a scream. The muscles of your anus began to contract furiously, trying to release your fingers. But Miss Fernandez would not allow it. Cum squirted from your cock and your whole body convulsed. It was your strongest and longest orgasm ever.
When the orgasm ended, you collapsed on the bed exhausted. You were still shaken a little. What was it?! You finished from anal penetration, and how. Does this mean you are gay? But you don't like men! For a moment, you imagined how a man's penis enters your ass, how it pushes it apart, and with horror you stopped this fantasy. Although men did not turn you on by themselves, but for some reason this thought aroused in you a lingering desire.
Did you feel that your anus was now gaping and stretched...

“Great, huh? I think that from today we will continue our classes in the same spirit!” Miss Fernandez was clearly pleased with herself. She gently caressed your body.
"Look what you've done." She took some cum and brought it to your mouth. You obediently licked her fingers. After an orgasm, your mouth was dry and you licked the sperm from your fingers with relief.
“That's enough for today. Now take a hot bath and relax well.”
Immersed in hot water, you comprehended what had happened. What happened seemed to you something wrong, shameful, forbidden and vicious. But at the same time so pleasant and inviting!
So, these additional classes have become something not just strange, but already simply frightening! Is it worth it to continue your extra classes with Ms. Fernandez?
Billy's Sissy Adventures.
Adventures of a young white sissy guy in sunny California and maybe somewhere else...
You are Billy Atkins, a white male student at Hayne College in Hautenville, California.
Updated on Jun 20, 2026
by Trom1806
Created on Aug 21, 2023
by Trom1806
- 2,429 Likes
- 1,132,348 Views
- 505 Favorites
- 285 Bookmarks
- 297 Chapters
- 69 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments