Slide

I looked at the e-mail. Another request for my tutoring services. I'd developed quite a reputation in the city.

I sent a reply asking for the usual details. Tracy, age 22, wanted help with advanced mathematics. She was living in a small apartment nearby, lived alone, and was a first-year graduate student, having completed her undergraduate work the year before and gotten her degree.

We worked out a time slot: Tuesdays and Fridays from six to nine p.m. She would pay me the usual hourly rate.

Tuesday evening rolled around, and I headed over to Tracy's apartment.

"Hello. You must be Ben."

"I am. Nice to meet you, Tracy."

We shook hands and she invited me in. I walked over to the living-room table, where her textbooks were. She had me sit adjacent to her, and we began to work through her math. Three hours later, she paid me and I rose to leave.

"You seem to have a good grip on this. Why did you think you needed a tutor?"

"Two heads are better than one. I didn't really have a good grip on any of it, but you helped me understand a lot."

"Seems like what you really need is a study buddy, not a tutor per se."

"Well, you can call it what you want, but you're the first person to succeed in getting the material into my head, so I intend to keep our schedule for the rest of the semester at least."

The semester had started one week ago.

"I'm glad I was able to help, Tracy. If you want to keep paying me to come by because you think it helps, I have no objection. Money is money and you're a nice person."

She blushed. "Thank you. See you Friday."

When I arrived on Friday, Tracy was wearing a shirt that exposed quite a bit of cleavage. Her breasts weren't the size of beach balls, but they weren't exactly mosquito bites, either. Probably around a C cup, though since I was a man, I was no expert on cup size. I put the thought to the side and focused on the math.

Tuesday, Tracy's top wasn't as revealing but her skirt showed a lot of leg. Once again, I kept things strictly professional.

Friday, she was wearing some sort of perfume. It was very alluring, and it took a lot of my will power not to comment on it. My ability to maintain strict professionalism was being severely tested.

Tuesday, she was wearing both a revealing top and a short skirt. My brain kept going places I didn't want it to go, but my mouth refrained from making any inappropriate comments.

Friday, she was wearing a robe and her breasts were practically falling out of the top of it.

Before we could sit down at the table, she turned and addressed me.

"Ben, are you gay or something?"

"No, Tracy, I'm straight as an arrow. Why did that come up?"

"Because you haven't responded to any of my efforts to draw your attention."

"You didn't hire me to have sex with you, Tracy. You hired me to help you with your math. It's called being professional."

"What if I want both?"

I pulled out a small tape recorder from my jacket and placed it on the table. "I intend to record the rest of this conversation. Do you have any objections?"

"I do not."

I pushed the button.

"The voices on this tape belong to me, Ben Jenkins, age 29, a tutor, and Tracy Calhoun, age 22, a graduate student who has hired me to tutor her. I have been tutoring her for three weeks. Ask your question, Tracy."

"What if I want you to have sex with me in addition to being my tutor?"

"We are both of age and unattached. You are quite attractive. If you agree that it will not have any effect on our professional relationship, that you initiated the sexual aspect of it and were not coerced into doing so in any way, and that any time we spend having sex will take place separately from the time I spend tutoring you, I am willing to enter into a sexual relationship with you. Do you agree to those stipulations?"

"I do."

"Good."

I turned off the recorder, placed the tape in my car, and returned inside for Tracy's three hours of tutoring.

After the three hours were up, Tracy stood up and pulled open the top of her robe, fully exposing her chest.

"Lovely," I observed.

"The idea is for you to kiss them, not compliment them."

"It's usual to start by kissing someone's lips, not their chest."

Tracy walked over to me, lifted me up, and pinned me against a wall. Her lips forcefully met mine. I returned the kiss gently. She pried my mouth open and rammed her tongue inside. I softly explored her mouth with my own tongue as she stuck hers what felt like halfway down my throat.

Eventually, she had to release my lips so she could breathe. I gulped in air and whispered, "Wow, you're a good kisser."

That drew a smile from her. "Glad you noticed."

I had a question for her. "You're a very attractive college student, so I know what made me willing to do this. When did you get the hots for me?"

Tracy grinned. "Since I saw your picture on your website."

"There's nothing about me that -"

She placed her finger on my lips, shushing me. "You have kind eyes and you're in a profession where you help others. Now kiss my breasts."

I kissed my way down from her lips to her neck, slowly exploring her skin. Tracy shivered as my tongue gently teased her sensitive flesh. I lightly nibbled her earlobe, making her giggle, then planted a kiss where her neck meets her shoulder. She held me tightly against her.

"Mmmmmm. Keep going."

I kissed down towards her chest, unhurriedly. She made soft little sounds of pleasure. I drew a line with my tongue through her cleavage, and she pressed her breasts into my face.

"Oooooh."

I kissed up from the base of her breast to her nipple, then took it in my mouth. Her body trembled and she pinned me more aggressively against the wall.

"Don't you dare stop."

I suckled harder and placed my hands on her butt, with only the thin robe in between. She moaned as I groped her rear. She pressed against me even tighter, and I felt something against my thigh. Something throbbing.

"Tracy?"

"Oh, yeah. Guess I should have mentioned I'm transgender. The nice thing is that since my mom named me after Tracy McGrady, I didn't have to change my name."

"I've never been... involved... with a transgender woman before."

"Don't sweat it. I'll guide you."

"Tell you what. Let's stop for now, and I'll come back tomorrow evening strictly for a date. No tutoring since it will be a Saturday, not a Tuesday or a Friday."

"Need a little time to adjust, huh? Okay, be here at 7 p.m."

I would need a little time to adjust, but it's not like anything had really changed. Tracy was still a beautiful woman who wanted me, it's just that she had a little something extra.

I spent most of Saturday reading up on tips for cisgender (a new word for me) men who were dating transgender women. It could be boiled down to "Treat her exactly like you would a cisgender woman, assuming you already know how to treat a cisgender woman like a person and not a sex object. If you don't already know that much you shouldn't be dating any sort of a woman."

I showed up at 7:00 with a small box of chocolates. Tracy smiled, let me in, kissed me, set the chocolates aside and took me straight to her bedroom.

"Get naked," she demanded.

"Yes, dear."

In two minutes both of us were naked and on her bed. Once again, she forcibly kissed me and jammed her tongue down my throat.

"Calm down and let's take it slow," I suggested. "I like you and think you're very attractive. Let's do long, gentle foreplay before sticking penises in body orifices."

"Normally I'd like that," Tracy observed. "And I'm glad you're trying to take my needs into account. But I haven't got laid in three years and I'm very ready. I don't have any STD's, so you can do me bareback and fill me up."

"I'm STD-free, also, and haven't had sex in over a year," I informed her.

"Good, then fuck me hard and cum in me."

Tracy dripped some lube into her butt crack and rubbed it in, then stroked me a couple times to make sure I was fully hard.

"What position do you want?"

"Missionary. I want to be able to look at you."

Tracy lay on her back and spread her legs. I carefully eased my way into her very tight hole.

"Mmmm, you fill me up nicely."

"And you feel awesome," I assured her. I moved in and out slowly at first, letting both her and me adjust, before establishing a smooth rhythm. Tracy's breasts jiggled a bit as I pumped her.

She noticed where I was looking. "Go ahead and suck them."

I leaned downwards and took her nipple into my mouth. Her body shivered as I suckled. Her legs wrapped around my hips.

"This is great, Ben. I've needed this."

"Glad you like." I continued sliding steadily into her rear. Her butt muscles squeezed my rod very pleasantly.

"Remember to fill me."

"Will do." I sped my thrusting a bit. Tracy more actively tightened her back-channel around my pole, trying to milk the cum out of it. I moaned and popped my head up so I could drill her with more effort. I put my hands on either side of her and started slamming her deep and fast.

"Oh my. Ben, you're making me..."

Tracy's words dissolved into a lustful scream as her body violently shuddered. Sperm shot out of her cock, coating her belly. Feeling her go off set me off, and I flooded her rear with my cum.

We rested for a moment, then cleaned up together in the shower, dried off, and returned to the bed.

"That's exactly what I've needed, Ben. Thank you."

"It was my pleasure."

"Spend the night, please. Now that the edge is off, we can enjoy each other and in the morning have more fun."

I agreed. We ate dinner, watched a movie together and we cuddled in the bed for a bit before we fell asleep with her head on my chest.

In the morning, we both did our morning routine and returned to the bed. She reached down and gently stroked my pole to life.

"I'd like to give you a tit fuck."

"Go right ahead."

Tracy got in position between my legs and wrapped my cock between her nicely round, firm breasts. I moaned as she slid up and down a bit.

"You can move your hips."

I began actively participating, thrusting my pole upwards into her cleavage. She shivered and used her hands to squeeze her breasts more firmly around my rod.

"Mmmmm. I can feel you throbbing."

My cock was indeed throbbing as I thrust it steadily between her orbs. Tracy dipped her head downwards and with each of my thrusts, she began licking the tip. That got me even hotter and I increased my pace.

Tracy opened her mouth and now she was actively sucking my cockhead with each thrust. My balls were filling quickly. I moaned and shivered, and she merely sucked the tip harder every time.

My legs tightened up as I approached the point of cumming. Tracy sensed what was happening and slipped her head downwards more, this time sealing her lips around my pole, taking the top half in her mouth. I blasted my cum down her throat, and she swallowed every drop.

When I recovered, I asked what she wanted me to do to reciprocate.

"Nothing right now. Like most transgender women, I'm more of a receiver. Just fuck the cum out of me at least once per weekend."

"You want me here every weekend?"

"Tutor me Friday evening, then spend through Sunday afternoon here."

"You like me that much?"

"Let's find out."

The next semester, she didn't have difficulty with her math, and we switched over to only dating. As promised, I fuck the cum out of her at least once per weekend, and she loves blowing me and tit-fucking me and sometimes just jerking me to climax. I love being in her. And when we're not having sex, with her.