Buyer's Remorse

Story Info
Marriage isn't always the best deal.
5.5k words
3.8
33k
33

Part 1 of the 2 part series

Updated 06/16/2023
Created 06/03/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
chymera
chymera
620 Followers

I think that I got all the education I needed my freshman year of college, because I missed out on a dorm room.

Her name was Wanda, and she was my landlady. Well, she and her husband Bill were my landlords. But Bill worked all day and Wanda was home. All day. Every day. As a freshman, I was at the bottom of the list when it came time to sign up for classes. Sophomores, who couldn't get their classes as freshmen, filled up most of the general ed classes I'd planned to take as a freshman. The only ones that I could get into were night classes. So, my scheduled classes were T-Th mornings and M-F 7:00 PM to 9:00 PM. Monday, Wednesday and Friday I was free all day, and had afternoons off Tuesdays and Thursdays.

Wanda was always around, saying "hi", offering me coffee or a coke, or just wanting to talk. I think she was lonely. There were three other tenants, but they were all gone during the day, so it was just the two of us. I felt strange around her; she was over twice my age, in her forties, but it felt like she was flirting with me like a teenager. I declined her offers, tended to mumble a return "hi" and flee to my room.

One hot October day I was attempting to draw the aorta for a biology paper when my red pencil broke. I lacked a sharpener and the only knife I had was my steak knife. I was hesitant to use a knife I used on food to sharpen a red pencil, so I headed out to buy a sharpener at the five & dime store. Before I'd walked three steps from my door, Wanda was there, asking where I was headed. When I told her, she said she had an extra sharpener. She said she'd go get it and then sent me back to my room.

When she returned, she came through my open door and to my desk to give me her sharpener. She looked at the partial drawings I'd made and in a flirty sing-song voice, said "What'cha doin'?", wiggling her hips and shoulders as she said it. I hunched over my desk, putting a point on my pencil with the sharpener, and muttered "Biology."

"Oh, goodie," she said. "I'm great at biology! Maybe I can help?"

I politely, but rather curtly, refused with a "No, thanks."

I kept my head down as I heard her walk to the door. When the door closed, I breathed a sigh of relief and finished sharpening the red pencil, planning how I would finish the illustration I was doing. Then I felt a hand brush my neck. I turned and saw Wanda. Really saw her. Naked. Ruffling my hair.

"You sure I can't help?" She made a moue face. "I'm really, REALLY good at biology!"

Well, I was an 18-year-old virgin. For maybe another half hour. Then I wasn't.

Over that semester, Wanda taught me about biology, and about how it applies to women. She instructed me in how to use my tongue, how to take advantage of different sexual positions, how to have anal sex safely and cleanly, and generally how to please women, in and out of bed. She drilled me on erogenous zones, using her body as our practice dummy. We had sex several times a day, most weekdays. And talked. She told me what most men do wrong in a relationship and in bed.

I was an apt and attentive student. And Wanda gave AP classes.

Unfortunately, for Spring semester the school found a dorm room for me. I tried to avoid it, but it was cheaper than staying with Bill and Wanda, so my father insisted I move. I ended up in an all-male dorm and had classes every day. I couldn't get to Wanda for days, but finally cut classes to go see her. I found her entertaining her new tenant. I went back to my cheaper dorm room, thought about what I had lost. Cheaper? Cheap is cheap. I flicked my roommate's discarded underwear off the floor and onto his bed.

I went from multiple orgasms a day to a three-week dry spell. I'm kind of nerdy and the girls in my classes seemed intent on the jocks or rich frat boys. I couldn't seem to get a date.

Then my dorm mates threw a party. Booze flowed and women were all over. I'd drunk too much and flopped down on the bed. A few minutes later a girl staggered in and asked if she could sit on my bed with me. We both felt like the room was reeling from the alcohol.

People passed in and out of the room, until it was just her and me. My roommate stuck his head in the door, saw us on by bed, sitting side by side, smirked at me, turned off the light, and closed the door. We sat for a minute in the near dark, lit solely by the LED lights on our rechargers and computer peripherals.

The girl's perfume reminded me of Wanda, and I thought, "What the hell!" I leaned over, gently nipped her earlobe, and tenderly kissed the spots on her neck that Wanda had pointed out. Soon, she turned and stared at me for a moment, before leaning in to kiss me.

In a short time, we were naked, and my tongue was playing a concert on her vulva. I played all the instruments, crescendoing on the clitoris. She hummed through her first orgasm. She squealed her second, but was screaming her head off as her third, fourth and fifth thundered through her, one after the other.

My door flew open and the men and women in the hall looked in to see who was being murdered. I lifted my head out of her crotch and embarrassed by my nudity, looked drunkenly at the faces in the doorway. Then my head was violently grabbed and shoved back into place while she screamed "Don't stop! Don't stop! Don't fucking stop!". The door closed on the sounds of laughter.

I, nerdy Robert Price, was now a legend. I had no more problems getting dates in college. Women wanted those screaming multi-orgasmic experiences.

The problem was that by senior year, I felt like a piece of meat. Wanda and I had had a lot of sex, but we talked. We connected. True we never dated outside of my room, but I felt like Wanda knew and liked me. Now my dates were in sorority rooms, hotel rooms or dorm rooms. Rarely did I get to go on a real date. It was always a rush to get back to bed. It seemed to be a competition between the Pi's and the Beta's to see who could achieve the most orgasms on a single date. They were calling it the "Price Bowl", and the Thetas were making book on it. Seems no one wanted my tongue, fingers, or dick to do anything that didn't directly lead to a climax.

Then I met Riley. She was a junior, but surprisingly was still a virgin. She came from a strongly religious family and had taken a purity pledge in high school. She was perversely proud of the pledge and her ability to honor it.

I ran into her in the library. Literally, ran into her. Knocked her down while trying to avoid a Sigma Chi who had objected to his girlfriend competing for the Beta's. I didn't know she had a boyfriend. I explained that to him, and I thought I had calmed him down. I promised to avoid her from now on. He accepted that until I opened my big mouth and said that it was a shame, since she was currently winning.

Anyway, flying down the stairs avoiding the jock chasing me, I slammed into Riley. Her books, purse and weirdly, her shoes all went flying in opposite directions. The librarians and the security guard rushed over. The jock looked at them, glared at me, and said "Later!" as he left.

I helped pick up Riley's stuff, apologizing profusely while I did. She brushed herself off, put back on her shoes, and smiling, said she was all right. She was pretty. I asked if I could buy her a coffee to further apologize. She accepted. After coffee, where we got to know each other, I coaxed her into accompanying me to a movie. I was going on a regular date.

I was infatuated with Riley. I dreamed about her that night and called her as soon as I thought it reasonable the next day. I asked her to dinner, and she accepted. It was wonderful.

I was walking on clouds until I entered her dorm to pick her up. Her roommate opened the door to my knock, took one look at me and closed the door in my face. I knocked again, waited, and knocked again.

Riley finally opened the door to glare at me. "Go away. Leave me alone." She started to close the door, but I stuck my foot out to stop it.

"Why?"

Her roommate pushed her way between Riley and the door. "Look, asshole. She took a purity pledge. You're not going to seduce her, so just leave her alone." She shoved me away, pulled Riley back into the room, and slammed the door in my face.

I tried reaching out to Riley but found my phone and email both blocked. I tried to approach her, but her roommate threated to report me to the dean for attempting to pressure Riley to have sex. She said with my reputation the administration would jump at the chance to expel me.

I retreated to my room. Other than classes and meals, I stayed in my room. The Pi's and the Beta's were pissed that I wouldn't continue the contest and girls who had dates set up with me were vocal about me standing them up. Rumors sprang up that I had an STD, maybe even full-blown AIDS, herpes, or hepatitis. I'd been threatened by the whole chapter at Sigma Chi and was hiding out in my room to avoid getting pummeled. Ironically, the rumor that spread the fastest was that I had come out of the closet, that I was gay.

After five weeks, things quieted down. I seem to have been pretty much forgotten. With only two weeks until finals, everyone had more important things on their minds. Except me. I still had Riley on my mind. Not being able to date her made me even more desperate to date her. Only, I couldn't even talk to her. Nothing Wanda taught me helped when you can't even talk to the woman.

Then, a miracle. I was headed back to the dorm after class when Riley stepped in front of me. "Can we talk?" she asked, taking my hand, and leading me over to a bench. We sat side by side, me looking hopefully at her face, her staring at the ground by her feet.

"I hear that you're not 'dating' (she used air-quotes to emphasis her scorn) anymore." She kicked at the grass. "Why not?"

"Because our one date showed me how shallow it all was. I'd thought we'd had a connection, but you treated me like damaged goods." I shrugged. "It hurt. I wanted that connection. I needed that connection. Everything else, everyone else, didn't matter."

She smiled at the grass, still not lifting her head. "We did have a connection. I felt it, but my roommate Janice said you were just trying to get in my pants, that I was just a challenge to you."

"I didn't even try to kiss you! I was happy just to talk with you." I twisted on the bench to face her. "Please, please go out with me. I'll tie my hands behind my back, I'll wear handcuffs, whatever you need to feel safe. But please, go out with me?"

She smiled and nodded.

We dated those last two weeks and through finals. It wasn't until graduation day that she finally let me......

Yeah, she let me. Let me hold her hand. I seemed to have acquired a new nickname in those final weeks. I was now Pussy Whipped. Ironic that neither pussy nor whips were involved, ever.

I'll spare you the details of our summer of dating. Suffice it to say that by the following September we'd progressed all the way to kissing, but not French kissing. But the more time I spent with Riley, the more infatuated I became. She was my world.

Labor Day weekend, I went all in. I got down on one knee and proposed. She accepted.

She was a virgin on our wedding night, and shy and hesitant, but she assured me that she was looking forward to consummating our wedding. I know I was looking forward to it. By the time we were wed and heading to the hotel, I'd been celibate for almost a full year. My bride didn't need anything blue on her wedding day. I was carrying enough blue in my scrotum for a battalion of brides!

Alone in the bridal suite, I took Riley in my arms and tenderly kissed her. Then I let passion erupt from under the rock I'd been keeping it buried under and crushed her lips with mine. My tongue hungrily thrust between her lips to wrestle with her tongue.

I was surprised when she pushed me away with an "Eww! Don't put your tongue in my mouth! That's disgusting."

"Sweetheart, that's French kissing! It stimulates passion. Everyone does it." I chuckled at her reaction.

"Not my parents! They don't do that!" She declared, indignantly. Then her face softened. "Honey, it's our wedding night. Can't we just go to bed. I want to feel your body. Help me take off my dress."

I reached for the zipper at the back of her neck and slowly pulled it down. There's something about seeing a woman's nude back that I find so incredibly sexy. So delicate, so curvy and soft looking. I helped slide the dress off her arms and shoulders and down past her waist.

I was taken aback. I'd seen Riley in swimsuits, bikinis even, but had not noticed before how angular and strong looking her back was, with wide shoulders and her straight, stiff back. If I didn't know better, I would have thought I was looking at a man's back. But as she turned, dressed only in bustier and bikini underpants, with garters and white stockings, I could verify that she wasn't a man. But I was thrown off by the mannish aspect of her back.

I pushed her back onto the bed while I softly kissed her lips, while keeping my tongue in check. As she sank onto the mattress, I moved down her neck heading towards her breast. She stopped me, sitting back up on the bed. "Now honey, let's get undressed and under the covers. Come on! Get those clothes of," she demanded.

I liked this enthusiasm. "Yes, Ma'am," I declared, stripping off the tuxedo, the studs flying everywhere as I pulled at the shirt. Damn, I'd have to find all those tomorrow.

I turned to get a quick glimpse of my wife's body as she dived naked under the covers. I pulled off my socks, pants, and underwear as I followed her into bed. I pulled her body into mine and we kissed and kissed again.

I ran my hands down her back and over her beautiful butt. She pressed her breast into me, smashing herself against me. I massaged her body and kissed her neck again. She giggled and tucked her chin into her neck. "That tickles!" she complained.

I tried to slip my hand between our bodies to manipulate her vulva, but she twisted her body away. "What are you doing?" she exclaimed. "You shouldn't touch me there!"

"But, Mrs. Price, you need a little foreplay to get the juices going, to get you set to orgasm...."

"No."

"What do you mean, 'No'?" I was kind of shocked. WTF?

"Look, honey. My mother explained this to me. You put your penis in my vagina, move about until you put your seed in me, and I have a child." She smiled brightly at me.

"Wait. What?" Riley had me confused. "No, there's a lot more to it. There's a lot of enjoyment before that. Look, just relax and ...."

Riley put up her hand in my face. "Stop it, Robert. Do you want to have sex or not. If so, then climb on top of me, now."

I've had more romantic request from drunk coeds that I didn't know, but hell, it had been a year and if this was what it took.... Well, I had plenty of time to straighten things out later.

I think losing her virginity was more painful for Riley than it had to be, but the deed was soon done. She kissed my cheek and rolled onto her side to sleep. I sat looking at her mannish back thinking that my wedding was starting out with the worst sex I'd ever know. I used to think that there was no such thing as bad sex, but beyond finally being able to relieve the ache in my testicles, my wife's deflowering had nothing more to recommend it.

I lay awake that night, contemplating the future. All that knowledge and training from Wanda and it seemed like I've married the one woman determined not to benefit from it.

I thought that the virgin bride was the one who was supposed to cry on the wedding night......

After a month of marriage, the term "unreconcilable differences" had a whole new meaning to me.

To the outside world, I'm sure it looked as if I had the world by the tail. My wife was beautiful, energetic and so attentive to me that she was practically glued to my side when were went out. I'd use the term "lovey-dovey", but there were lines she wouldn't cross or allow me to cross.

I could put my arm around her waist or hold her hand. I could pat her hand or caress her arm. God forbid I touch her legs or ass, or her breasts. According to her (and her highly religious mother), literally, God forbid. According to my wife and in-laws' belief, sex existed solely for procreation, breasts were strictly for feeding babies, and any kind of sexual activity or pleasure beyond that was Satan's temptations and a doorway to Hell and the fires of eternity!

None of this was mentioned prior to our wedding. I mean, yeah, my wife had taken a 'purity pledge' in high school and was extremely proud that she came to our marital bed a virgin, and yeah, I knew her parents were religious nuts. Hell, it was obvious the first night Riley took me to her parents' house for dinner. I had to stifle my laughter when we all had to kneel next to our chairs at the dinner table to say Grace before being able to sit down to eat.

And the twelve pictures of Christ in just their living room should have been a massive red flag. But in this day in age, who expects to marry into Cotton Mather's family of Puritans. My wife tended to dress a little conservatively, but I'd seen her in bikinis and halter tops with short-shorts.

Of course, the way she held me to just kissing, and not even French kissing, before the wedding, well, I just thought that that was part of her damn purity pledge. She always seems like a warm, willing body in my arms. How I had longed to squeeze her perfect ass or firm breasts! In the days leading up to our wedding I could have cum just thinking about caressing her naked back! Some days I could hardly walk for the ache in my testicles.

It wasn't until our wedding night that I learned that her mother had instructed her that sex was to be held to simply jumping on, pumping away and getting off! It couldn't get any worse, I had thought.

Yeah, I thought that until the second night of my "wedded bliss". That's when, in response to my amorous advances, I learned that sex was for Saturday nights. Not any other day. Could it get worse? Yes, when Riley had "her time of the month", that week was skipped. No make up days.

The Saturday after our wedding, I was ready for some release, and still convinced that given a chance I would bring Riley around with a few good orgasms. I was sure she hadn't had one on our wedding night. So, after the "pump and dump" that she insisted on for the first round, where again she failed to climax, I waited a while, cuddling and caressing the arm I was allowed to caress, as I recovered enough for round two. On our wedding night and now this night, I'd popped off way to fast when we'd had sex, in that I was suffering from blue balls going into each session. Now, for the second round, I intended to make sure that Riley had a good orgasm. That should open her religious mind to a real "come to Jesus" moment.

I lifted her chin and tenderly kissed her lips. As she returned my kiss, I began to roll over on top of her. She pulled back her head with a look of panic and demand, "What are you doing?"

"I was going to make love to you, darling." I smiled as I rubbed my chest against those firm breast and surprisingly hard nipples.

"NO!" Riley pushed at me but was unable to shift my weight. "NO! I'm way to sensitive from the first time!"

"What? What are you talking about?" Seeing her anger displayed on her face, I slid off her.

"It hurts, okay? I know I must let you and I will, but you can't do it when I'm already sore." With that she rolled over, presenting her back to me.

She was deaf to my entreaties; my explanations of what sex was supposed to be. How it's not supposed to hurt (although, some of the sorority girls seemed to enjoy a little of that), how it was the exact opposite. It was supposed to thrill, to excite and to overwhelm. Nothing I said seemed to get through. I gave up when she started snoring.

chymera
chymera
620 Followers
12