From Charity to Chastity

During one of my rare free periods, I was in the teacher's lounge at the same time as a teacher I'd formed a friendship with and who had been my mentor my first year. She was already in the lounge and had her nose in an oldCosmopolitan when I entered. Megan Hawthorne was about thirty-five and had been teaching Spanish and Latin for a dozen years. She was smart and funny with colleagues, with a quick wit and a tart rejoinder always at hand. She was all business in class. She was also the object of more than a few schoolboy fantasies. Some of the faculty, too for that matter. She was divorced and dressed to be noticed. Nothing that would raise eyebrows with the administration. She had the body for it. She had to know some of the boys practically drooled when they looked at her. Frankly, I think she liked being the MILF they fantasized about, though she didn't have children. But I know she didn't do anything to encourage them.

'Megan, can we talk for a few minutes?' I asked as I poured a cup of coffee. I grimaced when I took my first sip then dumped it in the sink.

'Sure, Evan,' she responded, not looking up from her magazine. When I'd gone to her for advice in the past, it had never been anything earth-shattering.

'I've got a problem and need some advice,' I told her. 'It concerns one of my former students.'

This time she looked up, but didn't look perturbed, only curious. 'Okay. What's the problem? I know you're not stupid enough to be romantically involved with a student. Or our conversation will be moving to Sheila's office.'

'No, I'm not seeing a student. I've gone out with a former student's older sister a few times.'

'How old is she? Or is it really he and you don't want to admit it?' she asked with a devilish grin.

I laughed. 'It's she. She went to school here but isn't a recent graduate. She's about my age. I met it her last year during a parent-teacher conference.'

'Is your former student still here?' Megan asked.

'She's a sophomore. I had her last year. She's not in any of my classes this year.'

'Are you serious about the older sister?'

'I don't know yet, Megan. Maybe. I like her. And it's clear she likes me. But I'm not sure where it might go just yet,' I answered.

'Well the sister is old enough to make her own decisions. Is the former student aware you're seeing her sister?'

'Yeah. She's been with us a couple of times during social events. So, she knows something is going on. She hasn't indicated she has a problem. At least not yet,' I told Megan.

'It's best you don't have the former student in your classes in the future. Notify the administration that the student shouldn't be assigned to you because of an outside personal relationship. Other than that, I don't see a problem,' Megan turned her attention back to her magazine, satisfied the topic was closed.

I breathed a sigh of relief. I didn't have to worry about ethical issues. At least not as far as Megan was concerned. I trusted her advice. She hadn't steered me wrong before.

'Who's the former student?' Megan asked, again leafing through her magazine.

'Charity Teagarden,' I told her.

Megan closed her magazine and put it down. She was grinning widely. 'Charity Teagarden? You're seeing Chastity?' she asked, sounding incredulous.

I wondered what the grin was all about. 'Yeah, is there something I should know?'

'No,' Megan laughed. 'I had Chastity in Spanish class all four years she was here. Nice kid. Pretty. Smart. Good athlete. I think she was all-state in soccer and softball. It's just . . .' she stopped herself before she finished.

'Just what?' I asked, wondering memory Megan had dredged up.

'Well, it's just she was so quiet. A bit of a loner except for her involvement in sports. She was whip smart but often distracted. I never heard of her dating or even showing interest in any of the boys in school with her. Not that they didn't try. While she was here, I was still chaperoning school social events. She didn't go to junior or senior prom. Or any of the student social events. In fact, outside of the soccer and softball teams, she didn't participate in any school activities. And if I recall, she didn't play soccer or softball her senior year. Some of the teachers thought she might be struggling with her sexuality.'

I didn't betray anything about Chastity's and Charity's home life. But I thought I understood her absence from school events. Senior year must have been especially difficult at home for Chastity to give up sports. Being an all-state athlete as a senior might have led to a sports scholarship. And if the events at my house after Brie's cookout were any indication, Chastity was sure of her sexual preferences. I went to my next class far more at ease.

Chastity and I spoke regularly and even managed to take a few weeknight meals together over the next month. Some nights we corrected homework together at my kitchen table. Though some affectionate clinches occurred, none got as heated as the night of Brie's party. In mid-November, Chastity told me her mother was going on a retreat with some of her AA friends for the Thanksgiving weekend. Charity and Chastity were invited to Brie's for Thanksgiving dinner, as was I. But I hadn't seen my parents since the previous August. My mother would have my head at Christmas if I didn't show up for Thanksgiving. I invited Chastity to come with me, assuring her we'd be home the same night. It would be late, but she wouldn't miss her weekend work shifts. I knew how important they were to her.

Brie encouraged Chastity to go with me. I told my mother I was bringing a girl but that she shouldn't get too excited. It was far too soon for her to start planning to spoil grandchildren.

Charity would spend Thursday night at Brie's. And would watch Kevin when Brie went to work Friday. I thanked my cousin and told her I owed her. She just smiled impishly, which scared me a little. But I decided I didn't care.

I picked up Charity and Chastity early Thanksgiving morning. I dropped Charity off then headed for my parents' house. Chastity wore a dress that ended above the knees for the first time that I'd seen. It wasn't anything that would distress my mother. But those great legs were on display for the entire ride. I'd started getting used to seeing a Chastity that wasn't disguising herself in frumpy clothing. She wasn't dressing to draw attention to herself. She just wasn't trying to be invisible.

It was a cold and clear day. An early season storm had dumped nearly a foot of snow the previous weekend, but the state and town crews had the roads in good shape for the holiday. The traffic wasn't bad as we drove through small towns on lightly traveled secondary highways. Mom must have been watching for us. She came out of the house and met us in the driveway. I got a quick hug and a kiss. Then got ignored like I wasn't there. She was all smiles, warmth, and welcome when she introduced herself to Chastity. So much for tamping down my mother's grandchild fantasies.

Chastity was overwhelmed at first. Except for my father, my extended family are all huggers. My father isn't an ogre by any means. Just a bit more reserved than the rest of the clan. But Chastity quickly got comfortable and was drafted into helping with meal preparation. My mother didn't need help. It was her way of getting acquainted with new friends. The day went well. As always, there was far more food than the crowd could consume.

When Chastity and I announced we had to get going, Mom brought out a bag of leftovers for us, mostly desserts she didn't want my father to eat. She gave Chastity a hug and turned to me, her face aglow. She whispered, 'I like this girl, Evan,' into my ear as she hugged me and kissed my cheek. My father smiled and shook my hand before I left. He hugged Chastity, which was unusual. Otherwise, he didn't say much more than goodbye to us.

It was well after dark, almost nine when we were finally in the truck headed for home. My grandfather gave me his '68 Ford pickup truck as a college graduation gift. He bought it new and maintained it like it was a Rolls Royce. It still looked new when he gave it to me. Chastity sat next to me on the bench seat, held my arm, and leaned against me as I drove.

'Your family is nice,' she told me with sigh. 'My sister and I are the last of the Teagardens. We have some family on my mother's side, but they don't live near here and don't stay in touch. Everyone else is gone,' she added wistfully. 'I've never been to a family holiday like this one. Thank you for inviting me. It was nice.'

We didn't talk much on the drive. Chastity slid away then rested her head on my lap. When she remained still for a while, I thought she fell asleep. Until her hand moved along the inside of my thigh, just above my knee. As she rubbed my thigh, I began to get aroused. I wasn't sure if that was what she had in mind. But it felt nice and I wasn't inclined to stop her. She'd figure it out soon enough, if she didn't already know the effect she was having. Her head was resting just above my thickening cock.

It wasn't long before I was fully erect. There was no way Chastity didn't know it. My erection was pressing against her cheek. She continued to rub my inner thigh until I adjusted my position in my seat a bit. It didn't change anything other than shift the pressure points on my butt slightly. Chastity slid her hand farther up my leg and lightly rubbed my now obvious erection. She turned her head slightly and nibbled on the head gently, the material of my chinos protecting me from direct contact with her teeth.

She sat up and reached over to undo my belt. She unhooked the waist and struggled with the zipper until she managed to get it down. She leaned against my shoulder and slid her hand inside my pants but not inside my underwear. I squirmed a little, wanting to relocate my cock, which was trapped in the right leg of my chinos. Chastity smiled at me and relocated it for me, so it was pointing up. If felt much better freed from the confines of my pants leg.

While Chastity leaned against my shoulder, she rubbed her hand up and down the length of my erection. I was on the brink of going crazy. I looked for a place to pull over but didn't find a suitable place to stop. Chastity continued to press against my erection, sliding her hand deliciously up its length, only the jersey material of my boxer briefs separating her hand from my erection. As my breathing quickened, her hand moved faster and held me a little tighter.

'Chastity, I'm going to cum soon if you keep that up,' I told her through gritted teeth as I forced myself to focus on driving the winding secondary highway. Fortunately, the road was nearly devoid of traffic.

'I know,' she whispered softly. 'I want you to.'

My breathing continued to quicken until I was nearly hyperventilating, Chastity moved her hand faster. When I finally felt the familiar tingle in my testicles, I grunted. Chastity gripped my cock even tighter as she stroked. Her thumb moved back and forth across the crown as she rapidly massaged my shaft. When I grunted again, my cock let loose a stream of ejaculate. Pins and needles engulfed my shaft, sac and heat shot up my spine. Fortunately, we were on a straightaway. I don't think I could have navigated any curves as a jolt shot through my body with each pulse of ejaculate.

When my orgasm abated, my breathing gradually returned to normal. Chastity continued to rub my softening erection, seemingly unconcerned about the massive wet spot being absorbed and spread through the front of my underwear. I glanced over at her. Her smile beamed at me. She bent down and kissed the end of my cock through my wet underwear. She nibbled on the head for the briefest moment, then sat back up and leaned against me. We finished the drive like that. Her head on my shoulder. Her hand caressing my cock through underwear growing stickier as I drove.

I wanted to return the favor and reached over to caress her leg. But she held my hand, stopping my progress up her thigh. 'Not tonight,' she said softly. 'Another time. I just wanted to do something for you tonight.'

When we finally pulled into her driveway, I put my truck in park and set the parking brake. I hugged her tightly and finally got to kiss her.

After we held each other for a few minutes, she moved away from me. 'I should go inside now,' she said softly. 'It's late. I need to get to bed. I'm working the lunch and dinner shifts tomorrow.' I started to fasten my pants so I could walk her to the door, but she stopped me. 'Stay, just watch until I'm inside and the door is closed.' She kissed me again, got out of the car, and went inside. I watched her go inside, staying in the driveway until she was inside and turned the front door light off.

The weeks between Thanksgiving and Christmas passed in a blur. I didn't see Chastity again until the end of the first full week of December, though we talked for at least a few minutes most nights. The school held a semi-formal dance for students each year just before Christmas break. I got to chaperone. Charity attended the dance. Brie dropped her off. Chastity was to bring her home. The dance ended at eleven.

I spent the evening monitoring the kids. Breaking it up if a couple got too risqué while dancing. Making sure they didn't sneak out to the parking lot to drink or get high. Or wander off into the school building for some reason. I hated being a buzz kill because I still remembered being a high school student. But I had a job to do. Two girls and one of my colleagues asked me to dance. I politely declined. It was a long night.

Chastity arrived a little early and came inside to say hello. She smelled like garlic, bread, and marinara sauce standing next to me. It made me hungry. We got stares when Chastity hugged me. I guessed they were checking out their competition, which I found amusing.

When the deejay announced the last dance at ten-fifty, Chastity pulled me onto the dance floor. She got a little round of applause for getting me out there. We talked for a few minutes before she left to take her sister home. I remained behind to help supervise the students who volunteered to take down the decorations and clean.

Chastity's student teaching gig ended the following Tuesday. We had dinner and did some Christmas shopping together Wednesday night. I had high hopes for the Christmas break. Chastity was working the weekends but neither of us had commitments during the week. The weekend before Christmas didn't go well for the Teagarden girls.

Chastity came home from work the Saturday before Christmas between her lunch and dinner shifts. Her mother was passed out on the floor, holding a nearly empty bourbon bottle. Fortunately, Charity had left early that morning to go Christmas shopping with Brie. An ambulance took the unconscious woman to the hospital where she was admitted. Her blood alcohol level was so high she might have died if Chastity hadn't come home. After she was out of danger, she was moved to a rehab and psychiatric ward where she would remain until after the new year.

The family always gathered at my parent's for Christmas. Since Beatrice Teagarden wasn't being allowed visitors during rehab, we invited Chastity and Charity to go with us after I discussed it with my mother. The Berry clan festivities were two-day affairs on Christmas Eve and Christmas Day. We'd be there at least overnight. I thought Chastity would have to work, but her restaurant was closed between Christmas and New Year. Chastity accepted the invitation to my parents'. Charity, a typical teen, was more like, 'Yeah, whatever.' Brie and I did a little extra Christmas shopping to make sure Charity wasn't left out when gifts were opened. We booked two rooms at a motel near my parents' home for Charity, Chastity and Brie. Kevin was spending Christmas with his father. I'd be in my old room at my parents' house.

My mother took Charity under her wing as soon we arrived. My mother did her best to make Charity feel like part of the family. I helped my father and uncle get the sleigh ready for use after a few minor repairs. It basically sat untouched between Christmas festivities. My aunt Debbie and her husband Bob arrived with their kids shortly after the sleigh repairs were completed. Their youngest daughter, my cousin Dina was fourteen. Charity and Dina quickly became inseparable.

We had a pleasant day. My grandfather drove the sleigh, everyone getting a chance to pile in at some point for a ride on the trails on my parents wooded thirty acres and some of the adjacent state forest. Everyone had too much to eat. Of course, a few had just a bit too much to drink but had enough sense to understand someone else should drive.

At the end of the day, Dina and Charity wanted to have a sleepover together. Everyone was gathering at my parents' house in the morning for breakfast, the gift exchange, and Christmas dinner. I gave up my room to them when Chastity, my mother, and Dina's parents okayed the sleepover. That left me without a room until Brie offered to bunk with Chastity. I took Brie's room.

I had a couple beers that evening so Brie drove us to the motel. Brie and Chastity checked us in while I unloaded the luggage. Our rooms were both on the second floor. I carried the ladies' luggage up to the second-floor landing, got my room key and a hug from Brie, then a hug and a kiss from Chastity. I ran down the stairs to get my own bag while they went to their room.

I usually slept in a tee shirt and a pair of gym shorts. But for some reason, I turned on the television and stretched out to watch the end of a John Wayne movie before getting changed for bed. I was drifting off when there was a knock on my door.

It was after ten. I wondered what was up as I went to the door. I looked through the peephole and saw Chastity, looking around nervously and hugging herself against the cold. I opened the door and ushered her in quickly; she wasn't wearing a coat.

I closed the door and started to ask what she wanted. I never got the words out. Chastity wrapped her arms around my neck and kissed me passionately. It left me breathless.

When we stopped to catch our breath, Chastity asked softly, 'Can I stay with you tonight?'

'Absolutely,' I answered. 'What did you tell Brie?' I don't know why I asked.

'I didn't tell her anything. I was fidgety while she started getting ready for bed. Brie asked if I was okay,' Chastity told me. 'I started to tell her I was fine, but when I looked at her, she was smiling at me. She asked if I wanted to be in your room instead. When I hesitated to answer, she told me to go to you. She said she likes us as a couple.'

'Is this what you want, Chastity?' I asked. Despite the time we spent together, I was still unsure where our relationship was headed.

'Yes, I do,' she responded quickly. 'It'll be easier now. I'm done with school. I haven't told you yet, but I start work at Lincoln Park High School after the holidays. One of their chemistry teachers is going on maternity leave. It's only for the rest of the school year, but it's a start. They told me there might be an opening next year. I'll keep my waitress job until I get something permanent, though.'

I held her close and kissed her gently. Her response was unexpectedly intense. Chastity reacted like a long, slow burning fuse had finally reached the powder keg. I had intended to go slow, to explore where she was willing to go. But when our lips met, I found hunger. Passionate, desperate hunger.

Chastity's tongue probed at my lips. When I separated them, her tongue entered my mouth and sought out mine. I probed the warm, wet depths of her mouth, while she explored mine. She groaned into our kiss, the vibration reverberating along my tongue and cheeks. Her hands were flying down my shirt as she undid the buttons. My belt was unbuckled, the waist unbuttoned and the zipper down in a flash.