Over 35 years I’ve had several of these encounters. If he response to this one is good I will publish the others
So I’ve taught college for over thirty years. I am now retired. Early in my career, I was married, and I resisted the occasional come on from my female students. Unfortunately my wife did not, and she left with a recent graduate 15 years her junior. She is a trust fund kid, so she could live the life of the cougar. God bless them.
Her departure left me more open to any advances by female students. I no longer had a wife to feel faithful to. I loved that some of my students were attracted to me, the attraction was mutual, to be sure. But I did not take up all of the students on their advances. I always passed on the “blowjob as extra credit” offer, as it was ripe for the scenario where the student rethinks her choices when leaving your office with a mouthful of your jizz.
I did, however, take advantage of student overtures when, first, they came on to me, and second, there was no quid pro quo expected or offered. That cut down on the number of encounters, but they were much more meaningful and memorable.
Over my career, I had amazing encounters with five different students (or their moms). All the students were aged 20-22. I’ll start with the first. If readers prove interested, I will write up the rest.
I met Jessie her first year at college and was immediately attracted to her. Truth be told, Jessie was the only one of my students that I ever truly fell in love with. But I never told her. Full red hair, fun-loving with a wonderful laugh. She took several classes with me, and we talked often outside of class. But we never socialized outside of the academic setting. She liked me as her teacher and I liked her as a student.
During her senior year, Jessie signed up for a month long course I was teaching in China with a colleague. We moved around a lot exploring China, and the students and I spent 18 hour days together exploring or traveling by bus. We all got to know each other well, and Jessie and I often spent long bus rides talking and laughing and enjoying each other’s company.
I thought maybe it was wishful thinking on my part, as well as years of inexperience, but Jessie seemed to be flirting with me. She rushed to sit next to me on the bus, and sat very close, always touching me in a way that any other student would have made me very uncomfortable. With Jessie, it just made me excited. As the class wore on, it seemed to me that Jessie’s clothes got skimpier and skimpier. Tops were looser, and on travel days she often didn’t wear a bra. When the bus windows were open and the wind was blowing, I was often treated to views of Jessie’s lovely C-cup breasts, capped with bright pink, often erect, nipples. I tried to be discreet in my fascination with her breasts, but I failed. More than once she caught me looking at those tits and imagining them in my mouth. Jessie always smiled when she caught me ogling those breasts, but made only token efforts to cover up. She took to wearing spandex running shorts that clung to the crack of her ass and attracted everyone’s attention when she walked by.
The thought of what pleasures lay under those skimpy clothes gave me a raging hard on during the daily bus excursions, and more than once I caught Jessie staring at my cock bulging through my pants. Once when I caught her staring, she just smiled and said “You must be having very pleasant thoughts, Professor.”
I was a bit embarrassed by her boldness and said “You have no idea. And you should stop looking at my crotch and flirting with me.”
She feigned shock and said “Why would I be flirting with you? You are just a dirty old man!”
We continued like this for a couple of weeks into the trip. Some days I could have sworn her tight shorts were damp in her crotch. She insisted that her flirting was just my imagination. I was about to bust.
By the second week, the students had settled into an evening routine where some went out to bars, if the town had one, and others gathered in my hotel room to watch Chinese TV and concoct their own translation for the endless period dramas that were the staple of Chinese television. My door would stay open, and students could come and go.
One evening students were watching TV while I was making travel plans for the class on my computer. Jessie was there, sitting on the bed with other students. She was dressed in a tight stretchy tank top that showed great cleavage, and short, loose flannel pajama bottoms. I couldn’t keep my mind or my eyes on my work, much to her delight. When she sat with her legs crossed, she angled her body so I could see up her legs and catch a glimpse of fiery red pussy hair. She enjoyed tormenting me, which was obvious.
As the evening drew to a close, students drifted off to bed until Jessie and I were alone; she sitting on the bed pretending to still watch TV and me still pretending to work. She kept adjusting her top, both to distract me I think, but the friction of the fabric also made her nipples hard, protruding through the thin fabric.
“Jessie, if you’re going to keep distracting me from my work, I will have to ask you to leave!”
“But I am just sitting here! I’m not doing anything!”
“Well, you’re not sitting very still, and you are flirting with me again.”
“Oh my God, I am not flirting with you, I am just watching television!”
“Okay, you’re not flirting with me. But if you are just watching television, you can do that in your own room where you won’t distract me.”
“Geez, my roommate is out somewhere and I just wanted company and you are throwing me out,” she said as she got up to leave.
“Stay if you want, just sit still.”
Rather than leave, Jessie closed the door and flipped the deadbolt. “I won’t bother you anymore, I just want to watch the end of this show.”
“Okay, fine,” I said.
She watched and I worked in silence for several minutes, and I thought everything was back to normal. But then she said, somewhat indignantly, “What difference would it make if I was flirting with you?”
I stopped working and looked at her. “None, I guess. It is just kind of a mean thing for you to do to your poor teacher. I might have to punish you.”
She smiled and giggled. “How could you punish me? Send me home from China?”
“I guess that wouldn’t work,” I said, returning to my computer screen. “I guess I would just have to spank you.”
She laughed again. “You couldn’t do that! Wouldn’t do that! You’re just kidding me!”
“Okay, if you say so” I replied, feigning indifference. “If you say so.”
She bounced off the bed and came over to the desk and stood in front of me. “Okay, I admit it. I’ve been flirting with you. Constantly. Mercilessly. Now spank me.”
I stopped working and looked at her. “You admit you’ve been flirting?”
“Yes, so punish me.” I looked at her long legs, her slim body and long, wavy red hair. I never wanted to take a woman as badly as I wanted to take Jessie in that moment.
I sighed. “Well, you leave me no choice. Turn around.” With a sly grin on her face she turned around and bent over slightly, hands on her knees, assuming the position for a spanking. “Just one more thing,” I said. I reached over and grabbed the hem of her pajama bottoms and gave them a tug. They slid down her legs and landed at her ankles, revealing a pale, pink and heart shaped ass. She caught her breath and stood up, but didn’t object. “A proper spanking requires a bare bottom. Now I have to put you over my knee.” With that, I took her arm and laid her across my knee, her lovely bare ass right in front of me. She gasped slightly but said nothing as I swatted her behind three or four times, thoroughly enjoying watching her pale skin turn pink under my lash.
After taking her punishment, she slid off of my lap and onto her knees in front of me. She rubbed my hard cock through my sweatpants, making it stand fully erect. I thought she would untie my sweats and suck my cock. But instead she stood up and pulled me to my feet. She stood on her tip toes and gave me a long, passionate kiss. I fondled her beautiful ass.
“So Professor, has my flirting been making you frustrated?”
“Uh, yeah. Terribly.”
“You’ve already took my pants off, and we both know what you want to do…”
“Yes. Definitely yes.” Jessie gave me another fantastic kiss. I thought I would cum in my pants like a lovesick teenager.
“Well, if you thought flirting was bad, tonight I am going to get you back for spanking me,” she said with a grin. “You are just going to have to wait—maybe forever.”
With that, Jessie pecked me on the cheek, bent over, careful to show me her ass and her tight pink asshole, and picked up her pajama shorts. She started to bounce to the door, but I grabbed her around the waist and pulled her close. Her pj pants dropped to the floor.
“Ooooh, Professor! You don’t want to wait do you?” Jesse said playfully.
“Nope,” I replied, dead serious. “I hope that’s okay, because I’m going to do it anyway.” I grabbed the bottom hum of her skimpy spandex top and pulled if off of Jessie’s body with one quick, rough snap. Jessie was now totally naked in front of me. She was neither shy nor embarrassed about her nakedness.
“I was hoping you’d say that,” she purred, turning and kissing me again, and stroking my stiff cock though my sweatpants. “But remember, I don’t have any birth control. We don’t want little professors running around.”
“No problem,” I said, scooping Jessie into my arms, loving that red hair cascading down towards the floor. Jesse caught her breath when I picked her up, but smiled as she wrapped her arms around my neck.
Without another word, I walked across the room and placed Jessie on the edge of the bed and spread her legs wide. I got down on my knees between her legs and wrapped them around my neck. I brushed my nose through her ample, trimmed red bush, savoring her feminine scent.
“Uhhhmmm…” Jesse moaned. I did the same with my tongue, playing with her pussy hair but not touching her skin. Her bum wiggled in frustration and anticipation.
“Please Professor…don’t tease…ahhh…don’t make me wait.”
I grabbed her ass and pulled her into my mouth, thrusting my tongue up inside her. I tongue fucked her, thrusting and wiggling my wet, slippery tongue as deep as it could go.
“Ohh! Ohhhhh! Yes…yes…please,” she whispered as her arousal rose. She grabbed me by the hair and thrust her hips at me, taking me deeper inside as the first waves of orgasm took hold of her body.
I slid my tongue out of her dripping wet pussy to catch my breath, replacing my tongue with a well-practiced finger probing for her G-spot. As my finger pressed against that soft tissue, I ran the flat of my tongue over Jessie’s engorged clit. She almost jumped out of her skin.
“My God! Keep doing that, whatever it was!” I was only too happy to oblige, rubbing her special spot harder with my finger, and scraping my rough tongue across her protruding clit. Jesse’s orgasm was quick in coming, as I felt her body tense, her hips pushed up against my face and she came almost like an explosion.
“Mmmm…mmmm…ahhh…geeeezus!” Jesse’s hips bucked in the air and thrusted as she sought to milk every sensation out of her body. She pushed against my face, she tried to get away from my tongue, but I held her ass, keeping her firmly in my mouth as I tortured her clit, causing her orgasm to continue for a minute or more. Finally her body relaxed. Jesse burst into incredulous giggles.
“I’m done. I’m dead. I’ll never cum again. You broke me,” she said, very much out of breath.
“I’ll wager that’s not true.” I started using my tongue to clean the juices from her beautiful pussy hair. I licked her essence from her pussy lips and got another moan when I spent some extra time making sure her taint was clean as well.
I stood and dropped my sweatpants, exposing my very eager cock. Jessie was still on her back, legs spread wide. Her eyes were glued to my throbbing cock, her face slightly apprehensive. I think she may have feared that I had forgotten our lack of contraception. But I had not.
I knelt on the bed next to Jessie, and pinned her arms over her head. I lifted my leg over her youthful shapely body and straddled her chest, nestling my balls between her tits. I let go of her arms and slowly started stroking my cock while locking her beautiful green-eyed gaze. Jessie smiled in anticipation. She brought her arms down and squeezed her tits together around my balls and began to play with them. I straddled her a little lower until I could slide my cock in her cleavage. I slid the length of my shaft between her breasts. Jessie gave the tip of my cock a little lick each time the head came close to her chin.
I had been anticipating this moment so long it did not take long before I felt myself close to cumming. I took my cock in my hand again and began stroking it more urgently.
“Open your mouth,” I commanded. Jessie opened wide and stuck out her tongue. I could feel my cock about to pulse, and my balls began contracting and pushing out my load. One final pulse and jets of hot, sticky cum shot across Jessie’s chest and covered her face and hair. Jessie licked her lips as some of my cum found its target in her mouth.
“Oh, God Jess! That’s it…oh fuck…” My mouth was spewing nonsense as my cock spewed my seed across Jessie’s face and hair. As my cock slowed its ejaculation, Jessie lifted her head and took the head of my cock into her mouth. With her tongue and lips, Jessie coaxed the last shots of cum out of my cock and down her throat.
Jesse now had a large load of my cum streaking and covering her face, hair and neck. Keeping her eyes locked on mine, Jessie started scraping my cum from her cheek and chin with her finger and depositing it in her mouth. My legs could not hold me up any longer, and I laid on the bed next to Jessie’s warm youthful body. Jessie laid her head across my chest and smiled brightly at me.
“You caught me by surprise, Professor. And I’m glad you did.”
“Yeah, sorry. Waiting was not in the cards for me tonight. I couldn’t wait.”
“Even though we didn’t do the deed, that was fun. I didn’t know what to expect next. I wish I hadn’t stopped taking my pills. Didn’t think I would need them, not having a boyfriend or anything. You have got to find some condoms, though. I want to see what else you can do.”
“We could, Jess. But I don’t think I would trust Chinese condoms,” I said, slipping back into teacher mode. “Have you seen how many people are in this country? Any country with over 2 billion people may be doing something right—but it isn’t making condoms!”
We shared a good laugh at that thought, but also concluded that condoms in China may well be too risky. We reluctantly put what few clothes we had back on and kissed good night.
About ten days later, our travels led to a very rural area in western China, Sichuan Province. Jesse and I had not had much chance to be alone since the night I spanked her. The group was booked for a couple of nights in an old communist era hotel by a nature reserve. It was clean enough and comfortable enough, with good food. By this time it was hard to find bad food in China.
But the showers in the rooms were a horror movie. There was no central hot water. So to take a hot shower, one had to open a valve to fill a galvanized metal bucket above the shower stall. This bucket had dire warnings—red Chinese characters with exclamation points. You could tell it was dangerous, but you couldn’t tell why. Our host explained that there was a heating element in the bucket. After filling the tank, you had to turn on the heating element. You did this by throwing an electrical switch on the wall—a switch that looked like the switch Dr. Frankenstein threw to bring his monster to life. Our host was adamant, however, before starting to take your shower, you MUST turn off the heating element or risk electrocution. Wiring without very good grounding apparently.
So, what does this have to do with our story? We had taken a morning hike into the reserve. After lunch we were scheduled to go to a museum, but I begged off. We were to be guests at a Chinese banquet that night, so I needed to steel myself for a night of toasting in my honor as senior teacher. I laid down on my bed to close my eyes for an afternoon nap. It seemed like I slept for about five minutes when the bedside phone rang. It was Jessie.
“Professor, I made a mistake, I need your help!”
“What’s wrong? Why didn’t you go to the museum?”
“I wanted to shower after lunch and I lost track of time and they left without me. That’s my problem.”
“I messed up the shower and didn’t turn off the switch before starting the water flow. The water’s running and the electricity is still on! I am afraid I did something terrible.”
“I’ll be down in a minute, I will take care of it.” It was the third such shower problem I’d dealt with since we got there. I got to Jessie’s room and knocked on the door. Jessie opened the door, and I saw she was just holding a towel over her breasts.
“Jess, what the Hell are you doing? I can’t come in when you are like that! The hotel staff might see and rat us out!”
“No, please, Professor! I’m not kidding around. I am really scared. Come fix it please.” The fear in her voice seemed genuine. I checked the hall to make sure no one had heard or saw me, and slipped into Jessie’s room. I latched the door behind me.
“C’mon, hurry!” Jessie said as she turned and headed toward the bathroom. The towel was only covering her front. She was completely naked from behind.
“Jessie! You’re not dressed! We can’t get caught!”
Her demeanor changed slightly. “Oh Professor, it’s not like you've never seen my ass before. It didn’t bother you the other night!”
I had to admit she had a point. “Okay, okay, let’s just fix this shower quickly before the others get back.” The shower area was completely open, there was no stall to speak of. I grabbed the plunger by the toilet and used the handle to reach through the water to pull the switch. I reached up and shut the shower flow too.
Jessie was standing against the wall, still clutching her towel against her breasts, but maybe less tightly than before. One of her shapely legs was bent in front of the other. Her long red hair was sweaty and wild from a day in the reserve. I couldn’t stand it. I had never seen anyone so gorgeous.
Without another word, I walked across the bathroom, grabbed Jessie by the wrists and pinned them to the wall above her. Her towel fell to the floor and my tongue slipped into her mouth. She offered no resistance, and moaned softly as she kissed me back. I kept her pinned to the wall as I bent down and sucked a pale pink nipple into my mouth. Jessie moaned a little louder. I ran my tongue down her body as I dropped to my knees in worship of her beauty. My tongue found her pubic mound.
“Oh God Professor! That feels so good. I want to fuck you so bad!” Jessie’s hips wriggled in rhythm with my tongue lapping at her clit. “I need your cock inside me!”
Without a word I rose and took Jessie’s hand and led her out of the shower room over to the bed.
“On your knees. Head down, bum up,” I ordered. Jessie looked a bit confused, but knelt on the bed while I took off my pants. Jessie watched while I stroked my cock to full attention.
“Head down.” Jessie obeyed, presenting me with her beautiful red trimmed pussy and pale pink asshole. I grabbed her hips and put my tongue deep inside her.
“Ohhh, uh-huh…” Jessie moaned and pushed her pussy into my face. I tongue fucked her pussy while one finger massaged her clit.
“Professor! Mmmmh! Oh God! I am going to…agggh!” Jessie couldn’t finish her sentence before a massive orgasm radiated from her tiny clit and shook her whole body. I continued to probe her pussy with my tongue. She gyrated her hips, fucking my face. She got quiet for a moment.
“Professor?” she said tentatively. I still had my face in her crotch.
“Mmmm?” I replied, not wanting to interrupt my snack on her snatch.
“Do you, umm, do you like anal?” I didn’t think it possible, but my cock got harder still at the thought of Jessie offering me that tiny pink prize. I answered her question by sliding my tongue slowly across her taint and stopping to rim her asshole.
“Ohhh…good,” she moaned. “I want you to fuck my ass.” My attention turned to eating her ass, and probing her tight hole with my tongue and a finger. She tasted amazing. Jesse was thoroughly enjoying her rimjob, while my finger was massaging her G-spot and she was playing with her clit.
I took my finger from her pussy and spread her ass wide to open her asshole for my tongue. As she relaxed, I could get the tip of my tongue in her ass. Just then another orgasm took over her body.
“Ah, ah, ah, oh God! Oh shit, Oh fuck!” as she pushed her ass as far onto my tongue as she could. “Professor, I want your cock in my ass. Now.” With that she bounced off the bed and rummaged through her suitcase, producing a small jar of petroleum jelly. I was still on my knees on the bed where she left me.
“Hold still,” she said as she kissed me again, putting her sweet tongue in my mouth. She took two fingers of jelly from the jar. Holding my cock in one hand, she slathered the head with the jelly, spreading down the length of my shaft. She then took both hands to slide up and down my cock, completely coating it with the jelly. Next she handed me the jar and turned around to present her ass to me again.
“Lube me up, Professor. Use a finger or two to lube inside my asshole.” I followed directions.
“Sounds like you’ve done this before,” I said, making stupid conversation.
“Just a couple times,” Jesse replied. “Both times were during my period and I really wanted to fuck. Just like I do now.” I worked two jelly-coated fingers deep up Jesse’s ass. She worked her hips to help me do the job right. I slid my fingers out of her ass and stood next to the bed. I grabbed Jesse’s hips and pulled her ass towards me. She gasped a bit when she felt the head of my cock at the entrance to her asshole.
“Oh, yeah. Do it,” Jesse ordered. I pushed my well-oiled cock against her tiny puckered asshole. I almost came when I felt her asshole start to spread and swallow the head of my cock.
“Mmmmm…ow…ow…owwww!” She cried softly. “Go slow, it’s really tight. No one’s been in there for awhile.”
“Tight is good. Tight is amazing,” I said as I worked the head of my cock to stretch and relax her anal sphincter. Jesse drew a sharp breath as I pushed another inch deeper in her ass.
“God that is so fucking nasty! That is just wrong….” Yet she was pushing against my cock hard with her hips, trying to get me deeper into her ass. She was making guttural, grunting animal sounds as I continued to violate her ass. She wanted to take me deeper. Her hips were grinding her ass on my cock now, moving me an inch or so in and out as she tried to relax her asshole so it wouldn’t hurt so much.
After a few minutes, she looked back over her shoulder at me and said “Fuck me as hard as you want now…”
The next few minutes are a blur. I grabbed a big handful of that fiery red hair and pulled it hard as I went balls deep in her ass for the first time. My cock was slamming in her ass, my balls were slapping up against her pussy. We were both gasping and groaning. Jessie was talking smack,
“Yes…yes…harder…oh God! Harder. Cum in my ass!” She was stroking her pussy while I reamed her ass. She reached a bit farther and grabbed my balls and squeezed.
“Oh God, Professor…give it to me…” Her bum squeezed my cock tighter each time she came. Her ample tits swung in rhythm with our bodies slamming together. I pulled her hair harder, pulling her head back like a bucking steed. I slowed my thrusting so I wouldn’t cum just yet. I was pulling my cock all the way out and slowly slid it all the way back inside her ass. It was so fucking hot, Jesse’s hair pulled back like a mane, watching my glistening cock slide in and out of that ridiculously tight asshole. I couldn’t help it, I was so close. I pushed my cock slowly into her ass one more time. My cock started pulsing and shooting my load into her bum.
“Ahhh…ahhhh…oh geeeeez.!” Her ass felt so good on my cock as I dumped a big load of sperm into her rectum.
“Tell me how much you love that. Does that feel good?”
“Oh God yes…yes…yessss…” Jessie moaned.
All too soon my cock was spent, but Jessie’s ass was full. I slid out of her, but had enough erection to slide back in a couple of times. She was still head down, but the beginnings of a nice creampie started oozing from her ass. It was beautiful. Jessie looked back at me over her shoulder. She was still catching her breath.
“Now you have to clean my asshole, Professor.”
“I know. I will go get a towel.”
“No. With your tongue. Clean it all up.” Jessie spoke firmly but did not raise her voice.
“What?,” I asked. I did not see this one coming.
“Clean my ass with your tongue. I saw it on a porn site and it looked really hot. Do it!” Her voice got a bit more commanding. I noticed my cum was flowing pretty freely our of her stretched asshole.
“Yeah I’m not into eating my own cum.”
“Like I care, asshole. I said clean my ass!” Jessie said with feigned authority.
“You talk pretty big for a little college girl who just took it up the bum.”
“What part of “lick my asshole” isn’t clear to you?” With that Jessie reared up and grabbed me by the hair and pushed my head down toward her messy asshole. I didn’t put up too much of a fight. While not a fan of eating my own seed, Jessie’s fucked and stretched asshole was relaxed enough that I could slide my tongue all the way inside. Call me a perv if you must, but I love the taste of ass, and Jessie’s was luscious. I started slowly tongue fucking her ass, cleaning my cum out of the way in the process. The taste of my cum and Jessie’s ass was pretty fucking hot after all. I slid a finger between her labia and gently stroked her clit. For all of her commanding tone, Jessie did not expect a tongue all the way up her ass and she melted again.
“God! Whoa! What are you doing? That’s gross!” she exclaimed without recoiling.
“Should I stop?” I asked, withdrawing my tongue from her ass while still massaging her clit. Jessie answered by grabbing my hair again and shoving my face into her crack.
“Not until you’ve finished cleaning my asshole! I said it was gross, I didn’t tell you to stop! Stick out your tongue…” With that, Jessie held me by hair and kept my face in her crack. Her hips began to move, riding my tongue with her asshole, taking me deeper up her ass. Her breathing quickened as her orgasm built in her body. Her other hand held mine against her pussy.
“Ummm…oh yeah, fuck, yeah. Yesss…” Jessie’s voice trailed off as her clit took control of her body, convulsing her body with ecstasy from head to toe, but keeping her ass on my tongue as she wreathed. When it had subsided, she collapsed onto the bed and I collapsed beside her.
“How did you like my ass?” she said brightly. “I loved you just taking what you wanted. But that last thing was gross. I loved it but it was gross.”
“Sometimes when you think it is gross it just means you are doing it right. I thought it was one of the hottest things ever. I would do it again right now. I loved everything about your ass.”
“I would do it again too…We’d better clean up, that field trip could be back at any time now.”
Jessie and I shared a quick, cold shower to wash off the detritus of our love-making. We needed to cool off, and we weren’t taking any chances with those bizarre Chinese showers…
The course was winding down and Jessie and I did not have any further encounters in China. For the flight back from Beijing to Detroit, the class was booked on one of those now-extinct Northwest 747. Being experienced China travelers, my colleague and I booked one of the only two-across economy rows back in rows 51 and 52. That way we wouldn’t have to sit with any of the students or strangers. Of course, the students often swapped seats during the 13-hour marathon flight.
I was in the window seat first getting settled when Jessie came down the aisle wearing her tiny, light blue spandex shorts and top. Funny, because she was in jeans shorts and a cotton top on the ride to the airport. She must have changed prior to boarding. This outfit covered very little, and I noticed that I noticed each male passenger (and a couple of female passengers) checked out her ass when she passed. Jessie plopped into the seat next to me.
“Jessie, this isn’t your seat,” I said, actually disappointed.
“It is now. My row was empty and the other professor was happy to switch with me.”
“Really? How about that?” Truthfully I was happy to share the space with Jessie, although I wasn’t looking forward to flying 13-hours with a raging erection. We chatted about the course, her post-graduation plans, and had a few stiff drinks each, ostensibly so we could sleep. After the meal, the shades were drawn and the lights were dimmed. It was cold on the plane and we both had blankets across our laps as we prepared to try and sleep for a while. Jessie visited the lavatory and returned to ask me to join the Mile-High Club, but we knew that the modern lavatories are really small, and the airlines are not very pleased when passengers try to pull that off.
I was just dozing off when Jessie took my hand under the blanket and held it tight as we drifted off to sleep. I woke up a couple of hours later I guess. Jessie was awake with her headphones on, watching a movie on the seatback screen. She looked over at me and smiled and returned to her movie. As I was trying to decide what to do, I saw Jessie out of the corner of my eye reaching for something under her blanket. Without taking her eyes from her movie, she pulled out her hand and dropped an object in my lap. I looked down to find Jessie’s blue shorts on my lap! She started laughing, still looking at the screen in front of her, as I quickly hid her shorts under my blanket.
I gave Jessie a quizzical look while she stayed looking at her movie. Under the blanket, she took my hand and guided it between her legs. My hand ran over Jessie’s naked thigh and stopped when I touched her soft pussy hair, already damp with her wetness. I broke out in a cold sweat. I could not believe that my young student was sitting next to me, pantless, on a crowded airliner! What if my colleague wanted her seat back? I started pulling my hand back, but Jessie grabbed my hand, selected a finger which she used to rub her clit. I took over from there. Jessie put her seat back, closed her eyes and switched her headphones to a music channel. I watched her face change expressions as I rubbed out a few on her pussy. She kept a pretty poker face, but I could feel her orgasm through her clit. After she had cum several times and created a large wet spot on her seat cushion, she opened her eyes and put her seat upwards. Still wearing her headphones, she mouthed “my turn” in my direction.
She put her hand on my cock through my pants and almost made me cum. With one hand she started unbuckling my pants and lowering my zipper. I grabbed her hand to stop her, shaking my head. I pulled at one of her earpieces.
“It will make a mess, Jess, we can’t do that here. I am not going to cum in the airline blanket.” Jessie made a pouty face and released her hold on my cock. Her face then lit up with an idea and she rummaged through her little carry on backpack, emerging with the skimpy cotton top she’d worn on the ride to the airport. She slid the top under my blanket and continued to unwrap my cock.
“You can cum in my blouse. It will catch it all.” Not being one to refuse a tug job from a beautiful girl, I put my seat back and closed my eyes, letting Jess do all the work. She now kept her eyes straight ahead on her movie while she tugged the length of my cock under the blanket. I don’t know how much of a poker face I had, but soon my cock was pumping streams of sperm into Jessie’s shirt. When I was done and she had cleaned off my cock, she withdrew the shirt from under the blanket and showed me what I’d done. The middle of the shirt was soaked with a good-sized wad of my cum. I passing flight attendant’s smile turned to a look of shock when she realized what she was looking at.
“You’re going to throw out that shirt? I asked.
“Hell no,” she smiled. “This is the greatest college souvenir ever!” This was several years before Bill Clinton and the blue dress, but I was wondering if letting a young girl walk off the plane with a shirt I had splooged on was such a good idea. I prayed that Customs wouldn’t get too curious. But I trusted Jessie to keep our confidence.
We both fell asleep for the rest of the flight.
Fast forward ten years…
I heard through the grapevine that Jessie was coming back to campus for her tenth reunion. We hadn’t had much contact in recent years, but I knew she was married with a couple of kids. I met the family at the welcome reception, and her husband Justin seemed like a decent sort. The two little boys had their Mom’s red hair. Jessie and I exchanged a knowing glance, but nothing more.
The next morning I was in my office, clearing away the papers of the semester just ended. Jessie appeared at my door in a short, halter-top sundress that let her breasts bounce as she walked. Those erect nipples I loved so much betrayed the fact that she wore no bra. My cock stiffened.
“Good, you’re here,” she smiled, “I was hoping we could visit for awhile.”
“Absolutely, please come in! Where are Justin and the kids?”
“There is a spouse and children trip to the zoo. They will be back in a few hours. This is supposed to be time for people to reconnect.” I noticed that she checked to make sure the door was locked on the outside before she closed it.
We met in the middle of the room and embraced the standard hug of old friends. But neither of us let go. Our eyes met and we kissed passionately. She still tasted the same. But I quickly broke away, “Jessie we can’t do this! You’re married now.”
“I know. I know I’m married. But I have been wanting you again for ten years. Don’t tell me you never think of what we did in China!” she said with a faux pouty face.
“Oh Jess, don’t think that. What we did in China is about the hottest nastiest thing ever. I think about it all the time, if you know what I mean. And your pantless thing on the plane…better than the Mile High Club!”
Jessie laughed, “I’m amazed that we didn’t get busted then. That must be a security breach.”
“There was one flight attendant who kept smiling at me every time he passed if I was awake. I always wondered if he knew what you did.”
“Me?” Jessie said indignantly. “That wet spot on my seat was your doing Mister. I was sitting there minding my own business.” We shared a good laugh while in each other’s arms. I knew then my attempt to keep Jess out of marital trouble were futile. I wanted her too.
“I can sit at my desk at work and make myself cum just thinking about you fucking my ass. I don’t even have to touch myself.”
“Justin doesn’t do anal?” I asked even though it was none of my business.
“My husband is hung pretty nicely and does well in the sack, but he refuses to eat my pussy and he won’t do me in the bum. He thinks it’s nasty and wrong. Which it is if you do it right,” she said with a grin, kissing my lips again. She started loosening my belt and unbuttoning my pants. “So I want you to take me nasty—hard, nasty, hair-pulling, the whole works.”
“Aren’t you worried that Justin and the kids will come here while we’re, uh, busy? That won’t be good.”
“No, but he won’t come here. I told him I would meet him back at the room when they get back from the zoo. The boys will be tired and he will have to give them a nap. Besides, I kind of think Justin knows where I am and what I’m doing here. He knows from my girlfriends that I fucked a professor in college. He has probably figured out it’s you. He told me to “have fun” when he left this morning. So I am going to take him at his word.” With that, Jessie reached into my underwear and wrapped her fingers around my stiff shaft. “Besides,” she said, “this part of your body is telling me you want this.”
Jessie reached behind her neck and untied the halter-top. Her dress fell to the floor. Jessie stood naked before me, capturing me again with those damn green eyes. As she tugged at my belt and zipper, she explained herself.
“After China I couldn’t think of anything else but getting fucked in the ass. A couple of boyfriends tried it, hated it, thought it was nasty—what’s wrong with men today?” She knelt down to remove my pants completely. She licked her lips as she jerked down my underwear to free my throbbing cock. My pants came off easily and were tossed into a corner of my office. Cupping my balls in one hand she took me down her throat. I almost came right then. Between licks of my cock, she continued,
“I can sit at my desk at work or in my car and make myself cum just thinking of how it felt when you came on my face that time. I can remember how your cum tasted. She licked a bit of cum from the tip of my cock. “Mmmmm…still tastes the same.”
“So Professor, here’s what I want from you,” she said as she stood while still stroking my cock. “I want you to take me, do me, fuck me, whatever you want to call it. I don’t care what you do to me as long as it is hard. Dirty. Nasty. Illegal in some states,” she said with a smile. “Don’t ask me any questions, don’t argue with me, don’t tell me what you are going to do, just do it. Any questions?” She retrieved a small jar of Vaseline from her bag and set it on my desk. “In case you go that route.”
“Still the bossy type, I see.”
“Yeah, like you don’t love it.” I had to admit it was pretty hot.
With that she wrapped her arms around my neck and probed my mouth with her tongue. I was amazed how I remembered her taste. That made me wonder if her pussy and ass still tasted the same. I sat her in my big desk chair and propped her feet on my desk, her legs spread wide. The chair tilted back, giving me a perfect angle on Jessie’s cunt. Jessie put her head back, eyes closed. I started finger fucking her pussy. Jessie started breathing harder, pushing her legs against my desk as she tried to ride my finger. I kept stroking her money spot until I saw her body tense with delight, and then release itself to ecstasy.
Keeping my finger inside her, I put my head between her legs and licked her clit with long, slow strokes. I could feel her body rise and fall with the touch of my tongue to her pink, engorged clitoris. If I rested my tongue on her clit, I could feel her pulse. Jessie grabbed my hair with both hands hand held my head between her legs. She held my face so tight against her pussy I actually had trouble breathing. Making her cum hard was my only chance to survive…
“C’mon Professor, eat me…lick me…” I went for the money move, running the flat of my tongue rapidly over her clit while massaging her G-spot. It didn’t take long.
“Uhhh…uhhh…oh geeezzus…yes…give…it…to…me!” Jessie’s body convulsed in my chair, almost overturning it if I hadn’t caught it with my free hand. That was one powerful orgasm.
“Oh my God…wow…shit,” was all Jessie could say. As I lifted my head from her pussy, I noticed that Jessie was playing with her nipples, pulling them hard and twisting. I lifted her legs off the desk and raised them high above her head, practically bending her in two.
“Grab your ankles, Jess. Hold them high, don’t let go.” Raising her legs while sitting in the chair exposed her asshole to me, in addition to her wet pussy. I hungrily and forcefully started rimming and probing her ass with my tongue. I slid two fingers inside her pussy this time. Her grunt told me she liked the tightness that two fingers created. I took my time with her asshole, licking and probing with my tongue, trying to get it to relax.
“Yes baby, eat my ass. My ass tastes nasty and you love it, don’t you?’ I looked up into Jessie’s eyes, her ankles up over her head, as I slid my tongue up from her asshole, across her taint and onto her pussy. I pulled my wet slippery fingers out of her pussy. Then without saying a word, I started sliding my fingers back inside Jessie, but this time one finger pushed its way into her tight asshole while the other finger slid back in her pussy. The expression on Jessie’s face told me she’d never had any double penetration, not even with fingers like today. And my mouth returned to her waiting clit.
“Jesus Christ, that feels good! That’s amazing!” Jessie gushed as I finger fucked her two nasty holes. Now I started sucking her clit into my mouth, torturing it with my tongue while Jessie was imagining she was getting fucked in the pussy and ass by two studs. Her orgasm came quickly.
“Oh my God…geezus…oh my God… fuck me like that, don’t…awwwhhh!” Jessie’s ass tightened on my finger as another orgasm coursed through her still-tight body. When her body stopped vibrating, I slid out of her and stood up. I grabbed her hair roughly and put her on her knees. My other hand held my cock for Jessie to suck. She didn’t hesitate. She took me in her mouth balls deep and worked my cock with her throat muscles. It seemed like Justin or someone has taught her a couple of new moves.
“Stand up,” I said, helping her stand with my hands under her arms. I turned her to my desk and bent her over it, elbows on the table. My wet cock parted her pussy lips and I began to slide slowly inside her warm, wet cunt. The smell of fuck emanating from her pussy was intoxicating. Two kids and she still had a nice tight pussy.
Jessie knew what I was thinking. “Um, yeah, I go to the gym every day since my kids were born,” she panted as her hips started rhythmically fucking my cock. “Do you think it was worth it, Professor?”
“Fuck yeah Jess. I never fucked your pussy in China, so I have had my own fantasies to fap to. This pussy is much tighter than my fantasies ever were.”
“Good. Fuck me long and slow. You have to save your strength to do me in the ass.”
“Don’t worry,” I grunted between strokes. “I think we’ve had the same fantasies there.”
Jessie looked back at me and smiled, tossing her long red hair. “I need your help to act out another fantasy, if you are up for it.”
“Oh yeah,” I managed to grunt. There was not a lot of blood in my head at that moment.
“Let me go to my purse for a minute,” Jesse said, sliding off my wet member. “Be right back.”
Jessie moved over to where her bag was sitting on the floor. She made sure I was looking when she bent at the waist to go into her bag, showing me her gorgeous asshole and dripping wet pussy. She stood to show me what she was looking for.
“I call it ‘The Professor’” she said, holding up a large, pink, penis shaped silicone vibrator.
“I should be so lucky, Jess. But thanks for the encouragement.”
Jessie wet the shaft of the toy in her mouth, propped one foot up on a nearby chair and slid the large toy deep inside her. After a few seconds, she withdrew “the Professor” and handed it to me.
“I just needed to wet it,” Jessie said matter-of-factly as she bent over and put her elbows on my desk again. “Turn that bad boy on and slide it into my pussy. It’s the best sex I get some days. Then fuck me in the ass.”
The toy purred softly as I switched it on. I got down on my knees because I wanted to watch that toy spread her labia. I picked up the petroleum jelly from the desk and dipped the tip of the toy into the jar, coating the head enough to get inside easily.
“Mmmm…” Jessie moaned softly at the sight of her well lubricated toy. “Probably not a bad idea.”
“Spread your pussy,” I said. Jessie reached down and obligingly pulled her labia apart. The sight of her ass hole and the smell of her fucked pussy was almost more than I could stand. Jessie’s flattery aside, her vibrator was quite a bit larger than my cock. I would have been proud to pack something like her Professor toy. I wondered to myself if she’d ever taken this toy up her bum. I placed the head against her pussy and began to gently push, twisting it slightly as I pushed. Jessie grunted, as her cunt relaxed and let in the new invader.
“Push,” she whispered between grunts. “Push harder.” Her cunt swallowed up this large toy. I guided her hand to hold the vibrator in her pussy. The toy purred happily as I dipped my cock in the Vaseline jar and got a nice wad of jelly on the tip.
I held my oily cock, and put the head against her asshole and started to push. With the help of the lube, her tight little pink asshole gave way without much resistance. She’s putting something up there, I thought in passing.
“Mmmmm…yeah…that’s what I want baby,” Jessie purred as my cock disappeared up her ass an inch at a time. “Push it in all the way…yeah…fuck me hard...please.”
I needed no further encouragement. Jessie’s ass felt as hot and tight as it had ten years before. And she loved a cock in her ass maybe more than she did ten years before.
“Ah…did your cock get bigger, Professor? I love that.”
“No,” I grunted. “I wish. I think your ass got tighter,” I panted as I began slamming my cock inside her with more urgency. Jessie moved her hips with mine, slapping my balls up against her pussy. I could feel the vibrator humming away inside her cunt as I put my cock up her ass to the hilt.
“Oh! Yeah! Fuck…just fuck me like that…just like that…” Her hips slammed hard against mine two or three more times before her whole body began to tremble and shake as she came hard on my cock, squeezing me with her tight anal sphincter.
“Ahhhhh! Ahhhh…oh…yes…Prof—Ahhh…” The waves passed after a minute of hard breathing. I was still sliding slowly in and out of her asshole. I loved watching my cock disappearing and reappearing from her butthole.
“Geez! I never did that before, you know both ways. Wow. I’ve missed having my ass fucked for ten years…ten years! Why’d I wait that long? That was amazing.” Jesse pulled the vibrator from her pussy as she slipped her ass off of my still erect cock. Turning to face me, she kissed me and then locked my gaze with those beautiful green eyes.
“Your turn, Professor. But I want it in my mouth,” she said as she dropped to her knees, still stroking my cock. My cock was still slippery with the lube and her ass. If she minded the taste, she didn’t let it show. Jessie licked around the head slowly, eating a bit of cum she coaxed from the tip. Then she pulled and squeezed my balls as she slid me into her mouth and down her throat. She massaged my balls and even took a tentative finger and massaged around my anal opening.
“Oh, God Jessie, you are going to make me cum…so hard…Jeesus…” was all I could muster. She kept swallowing my cock faster and faster. I could not hold on any longer. I grabbed a big handful of her tousled red hair and pulled her head off my cock.
“Stick out your tongue…let me watch you eat it…” Jessie obeyed and laid the head of my cock on her tongue, her mouth open wide. She flicked her tongue on the base of my cock and gooey streams of cum shot into her mouth and onto her lovely face.
“Oh yeah…fuck yeah…that is so hot…don’t swallow it baby, show me your mouthful.” I could see Jessie’s mouth filling with my milky white semen, and still she coaxed more out of my balls. Drips started escaping from the corners of her mouth, running down her chin and onto her firm breasts. By the time she got it all, her mouth was overflowing, dripping more cum onto her breasts. She stood, opened her mouth and showed me all of my seed that she’d sucked out of my cock.
“Fuck that is so hot,” I whispered to myself. “Now swallow it baby, let me hear you swallow my load.” Jesse gulped it down without hesitation, and licked the remnants from her lips. She looked down and took a fingerful of jizz from her breast and rubbed it onto her erect nipple. With her other hand she grabbed my hair and pushed my head down.
“Now it's your turn to swallow some cum,” as she guided my mouth to her semen covered nipple. I licked her hard pink nipple clean before sucking into my mouth and biting it hard.
“Oooh…ouch…now the other one” she whispered as she rubbed some cum on her other nipple. I cleaned that one of all my cum and flicked it with my tongue before biting down and pulling her nipple with my mouth.
“Oooh…oh…yes…” she said to no one in particular. For good measure, I licked the rest of my cum from her breasts before collapsing into my desk chair. Jesse jumped into my lap and wrapped her arms around my neck. She kissed me deeply, giving me one more taste of my semen.
“Wow.” That was all I could say. I was truly fucked stupid and almost speechless.
“I needed that, Professor. You have no idea how much. And it was perfect,” she smiled at me. “Now I have new memories to make me cum at work.”
My office was a mess, from Jesse’s sun dress and my pants on the floor, to the stack of papers we pushed off the desk during a moment of intense passion. Jesse got off my lap, and still naked, began to straighten up the fallen papers.
“Leave it baby. I like having my office look like I just got my brains fucked out. I may never clean it.” Jesse was slipping into her dress as her feet slipped into her sandals. I reluctantly tied her halter straps behind her neck while she held up her hair. I kissed her neck one more time and murmured softly,
“I love you Jessie.”
“I love you too, Professor. Always have, always will.”
With that, and a small wave at the door, Jessie left my office, and my life, forever.