The Last Time

The Last Time

A retiring colleague asks for a favor.

All characters are at least 18. The characters in this story are flawed, just like you and me. Sometimes they make bad decisions as they struggle to live their lives, or in this case to end their lives. All characters and situations are complete fiction, a product of my fertile imagination. Any similarity to actual people and situations is purely a coincidence. All constructive criticism is welcome.

*****

As chair of the search committee, Brenda was the driving force in getting me hired at the college a dozen years ago. Since then she had been my mentor, advocate, and friend. Back in September, she submitted her retirement paperwork, effective July 1st. She had been a professor for 42 years. As the department chair, I had to sign off on it. Brenda, now 73, had earned her retirement.

My friend is a petite woman. She has pictures of her children and grandchildren all over her office. Brenda is also a devout woman and observant Jew. She always took the High Holy days off and observed other Jewish traditions. She is extremely modest and I have never heard her use profanity, a vulgarity, or an obscenity.

It was the first Wednesday in May, the end of the school year. Finals started on the following Monday with Commencement a mere two weeks away.

I sat at my desk grading papers, when Brenda knocked on my door frame, "Got a minute?"

"For you my friend, I have hours not minutes."

She closed the door and sat down across from me, "You have always been so kind to me."

"That's because you have been so nice to me. I wouldn't be here if it wasn't for you."

"I was just following my intuition and I was right. You're the best hire this college has made in forty years."

"Now, you're being kind. Are you ready to become a professor emerita?"

"Yes and no. It will be a change, but I'm prepared. That's why I'm here. I have a favor to ask of you."

"Anything for you Brenda."

"Before you say 'yes', you need to hear my proposal."

I nodded, "Fair enough, but I'm still going to say 'yes'."

She crossed her legs, modestly pulling her skirt over her knees. She leaned back, "As you know, my husband died 19 years ago. I finished raising my sons myself and now I help with my grandchildren."

"You have eleven?"

"Yes. Eleven grandchildren." Brenda averted her eyes, then looked back up at me, "This is hard. I need to start at the beginning. How much time do you have?"

I looked up at the clock, 2:06, "I'm free until 4:30. You may have every minute."

"Thank you. As you know I grew up out on the plains of Nebraska. My family were farmers. You didn't know this, but I grew up Lutheran."

"I didn't."

"Bradley was Jewish and I converted when I married him. I digress.

"There was no way I was ever going to college. My family couldn't afford it. This was 1968 and a poor farm girl didn't have many prospects. Most likely I'd get married to one of the boys from a neighboring farm and pop out a bunch of kids. I'd live and die all within a hundred miles of the place I was born, living a hardscrabble life.

"Since I was going to graduate valedictorian, my high school guidance counselor convinced me to apply to several scholarships. Well, I applied to several prestigious programs and I won one of them! It was a full ride to any Christian college in the country. My guidance counselor helped me look for a college. When I saw the catalogue for Pepperdine, I knew that was the place for me. Back then, it wasn't in Malibu. It was in South Los Angeles. It looked perfect. Palm trees, warm weather, no snow. That September I packed two suitcases and got on a Greyhound bus bound for California.

"California was quite the shock for me. This was 1968 and hippy culture was everywhere. Lil' ole Nebraska girl didn't even know there was such a thing. That fall I had my first drink. I smoked pot for the first time. And most importantly, I had sex for the first time. That was a life changing experience for me. Right now, you see me as this modest grandmother. Back then I became a fucking machine."

My face must have registered a shock at Brenda's use of the f-word because she laughed out loud.

"Let me tell you, back then I was a different person. I rushed for a sorority. At first, I'd only have sex on the weekends, but then it became a daily thing. I didn't care who I had sex with, I just needed sex. No, my body craved orgasms. I fucked every guy I met.

"I developed a reputation on campus as a slut and I tried hard to live up to that reputation. My sorority sisters and I would go to a frat party just for the sex. We'd strip naked as soon as we got there. On a whim I'd drop down and blow a guy. Maybe fuck them. I'd have some kind of sex a dozen times at a party. Freshman year I probably had sex with half of the guys on campus.

"This was also Los Angeles. My sisters and I would catch the bus up to Hollywood and we got to see some of the movie stars. We wanted to have sex with them, but we weren't sure how to go about setting that up.

"We learned that one of the guys in a frat worked security at Paramount Pictures. He got one of my sorority sisters a date with a famous actor. Afterwards she fucked his brains out all night and suddenly we had an in. That actor talked up our sorority and we all started having dates with movie stars. By dates I mean fuck fests. All night orgies."

"Any names I would know?"

"Oh, yes, but it wouldn't be right for me to say. From there we branched out into rock and roll. Back then they called us groupies. Hanging out with rock musicians introduced me to group sex."

I raised my eyebrows and Brenda laughed again, "At first I would have sex with one guy after another, but soon I learned how to handle more than one guy at a time."

I couldn't believe she was telling me this.

Brenda kept her head lowered, "That summer, before a concert at the Hollywood Bowl, one band made me airtight for the first time. It was amazing having three cocks in me at the same time. Anal was my new thing. I wanted multiple men all the time after that.

"In the fall, I volunteered to do an entire frat. Sixty guys. Most of the time with all holes filled. I was in heaven being a cum dump. I'm sure it was a lot more than sixty, because I had a cock in one of my holes for over five hours. One of my sorority sisters said they were bringing in guys off the street to fuck me.

"I moved into harder drugs and it started getting bad. For example, many years later I was reading No One Here Gets Out Alive, a biography of Jim Morrison of the Doors. There is a scene where a woman passed out naked on a table, spread eagle. The author wrote, 'we all had a poke'. As I was reading that, I realized that that woman was most likely me. Many times I'd wake up in a strange place with cum flowing from my cunt.

"Two of my sorority sisters and I were backstage at Altamont in 1969. I had just turned 20 and I was getting fucked by all these famous men." She looked up at me, "I know what you're thinking. Yes, I fucked all of them. I've lost track of how many men I've had sex with. Over the years I've probably had sex with a minimum of two thousand men. Most likely that number is four or five thousand. I have no idea. That's probably a record for a non-professional.

"I've had big cocks and little cocks. A couple of huge cocks. I didn't care as long as the cock was in one of my holes.

"Believe it or not, I still had excellent grades. When I graduated from Pepperdine, cum laude by the way, I had to get away from L.A. because of my reputation. I ended up at the University of Minnesota where I got my doctorate. That's where I met my husband. Since that day, I have had sex with only one man - Bradley."

"Brenda, why are you tell me all of this?"

"William, I'm dying."

What!

She leaned over and took my hand, "I have an inoperable brain tumor. I have refused chemo and radiation. I don't want to go through that. The doctors have given me six months to live. I don't plan on waiting that long.

"My last day on Earth will be July 5th. I will fly out to my son's house in Portland, Oregon. I'll watch the fireworks the night before. Then I'll go to a place that specializes in assisted suicide and leave all that I love.

"Before I go, I am hoping to relive just a little of my youth." She pointed at her crotch, "I have a dried up, old cunt that no longer provides me with any pleasure, but I hope you will let me give you a blow job. It will be my last sexual act. I have missed having sex since Bradley died. Just one last time I want to experience that amazing feeling of control and intimacy, of having a cock in my mouth, the lovely taste of semen."

How do I say 'no' to a request like that? I can't. "I will gladly be your last lover."

A wan smile spread across her face, "Thank you, Will. I have a proposal. How about if we meet here on Saturday morning around nine. I find my body works best in the morning." She handed me a plastic baggie, "There is a Cialis in here. If you could take it an hour before hand, you will be ready for some sustained sex. I like I said, I have a dried up twat. They used to call it vaginal atrophy. It means I don't produce my natural lubricants anymore. Plus, because I take Lexapro, I am incapable of having an orgasm. Trust me I have tried ... a lot. I will suck on you for a long time and eventually have you cum in my mouth."

We were both quiet for a few moments. She asked, "Any questions?"

"Why me?"

"I love you, Will." She looked down, then back up, locking eyes, "More than you will ever know." She swallowed hard, "I hope you care for me."

I nodded, "You are one of the dearest people I know." I laughed, "Although I always thought of you as my big sister."

She smiled, "Well, you know what they say, incest is best." She stood and squeezed my hand, "Thank you my friend. See you Saturday."

She turned and left.

*****

I didn't see Brenda the rest of the week. After much consideration, I decided that I would at least offer her some vaginal sex. I bought a tube of KY at the drug store and borrowed a yoga mat from a friend of mind. We could have sex on the floor of my office.

Saturday morning I got up at seven, showered, and shaved extra close. I just wore jeans and a t-shirt. I went commando to make things easier. I arrived at my office around 8:40. I didn't want anything to ruin this for Brenda. I even went to the men's room and brushed my teeth a second time. I kicked off my shoes and socks before she arrived.

Brenda appeared in my doorway a few minutes before nine. She wore a yellow sundress with blue flats. She had put a little curl into her grey hair. She looked lovely. I could imagine what she looked like fifty years ago.

I stood up, "I don't know how you feel about this, but I bought some KY and a yoga mat. If you would like to try having regular sex, I would be cool with that."

Her mouth moved, but nothing came out. She smiled and a tear rolled down her cheek. Finally, she whispered, "I'd like to try."

I stepped over and took her into my arms. I gently kissed her.

She groaned, "Oh, that's nice."

I cupped her cheek and began kissing her with more passion. She wrapped her arms around my head, pulling me down toward her face. Her lips parted and our tongues entwined. Sparks shot down my spine and my cock stirred.

Brenda broke the kiss and whispered into my mouth, "Wow. I haven't had something like that in a very long time."

"Let's savor the moment."

She kissed me again. We stood there kissing for quite a while, holding each other. Enjoying one other.

Brenda stepped back, "This is nice. Let's spice it up a little." She reached down and pulled her sun dress over her head. She stood there in all her glory. Even at 73, Brenda was a beautiful woman. She had smaller than average breasts with lovely pink nipples and just a touch of sag. There were wrinkles, but not many. Her slim body had very little fat. Her hips flared nicely. She'd trimmed her thin, grey pubic hair.

"You are a beautiful woman, Brenda."

"Thank you. You are kind."

"And I am correct." I pulled my t-shirt over my head.

Brenda stepped forward and ran her fingers through my chest hair, "Back in the day, hair was the thing. Girls had it. Guys had it. Not so much today." She kissed me, "I love a hairy man. So virile." She undid my belt, "I feel like a young woman again, undressing a handsome man."

A burst of fear rushed over me. Brenda had had seen, sucked, and fucked thousands of penises. How would she react to mine?

She unbuttoned my jeans, then knelt before me. I started to help, but she interrupted, "Let me do this." She slowly unzipped my fly. The two halves separated, and my pubes came into view, "You still have some very red pubic hair Mister Man." Her hands pushed my jeans off my hips and they fell to the floor, "Oh, that's nice."

She lifted my shaft and kissed the head, "Mmmm." A little suck. Brenda looked up at me, "Perhaps you would be so kind as to have a seat."

"Gladly." I stepped out of my jeans and sat naked in my chair.

She knelt between my legs, "Over the years I have found that I get a tremendous feeling of power and control when I am between a man's legs, his cock under my control."

Brenda produced a rubber cock ring, "I was thinking one of these would keep you harder longer." She slipped it onto me, then lovingly took my tumescent shaft in her hand. A drop of pre-cum glistened at the tip and she licked it off. She raised the head to her mouth, "Oh, my." She pressed her soft lips to the head, then looked up at me, "Perhaps because I married a Jew, but I prefer circumcised men. You're perfect, Will."

She traced the tip of her tongue around the sensitive crown of my cock, "Hmmm." Next around my circumcision scar, then long licks the length of my shaft. I rapidly moved from tumescence to raging hard-on.

"Put your feet up on the desk and scoot forward."

I knew what came next. When Brenda's tongue flicked my anus, a shiver shot up my spine. A groan involuntarily escaped my lips.

Brenda looked up into my eyes as she licked my shaft like a lollipop, "I want to make this last as long as possible. If you feel an orgasm coming on, let me know." I nodded. "I'm going to take you to the edge a couple of times."

She began sucking the head, while stroking the shaft. All the while her eyes never left mine. I felt a moistened finger circle my anus. She probed into my ass and touched my prostate.

"Oh god, Brenda."

She gave my cock a lick, "You like that? I know how to drive you wild."

I felt her finger in my ass, sparks flying up my spine. Her mouth bobbing, sucking. In less than a minute I felt my orgasm approaching, "Stop, Brenda."

Rather than stop, she shifted her focus to areas that weren't as sensitive, like my balls and perineum, "Very nice. Very nice. So, here's my plan. I'm going to take you up on the traditional sex offer, except I'll be on top. We'll do that for a while, then we'll move back here. I want to have your load in my mouth."

I spread the yoga mat and laid down on my back.

Brenda stood above me straddling my torso, "I hope you don't think I'm weird, but I have fantasized about having you in a position like this."

She got down on her knees and pressed an unknown quantity of lube into her vagina. Then she squeezed some on my cock, spreading the KY liberally over me.

Brenda laughed, "I hope this is like riding a bike."

She placed the head at her opening and gently pressed me in, just an inch or so, then back out, "I feel like a born again virgin. My first time I wasn't in control. For my last time, I'm in full control."

Again, she pressed me into her vagina, a little further this time. Her pussy as tight as I have ever experienced. She closed her eyes and began the process in earnest. In and out, little by little, Brenda pressed me into her womanhood. After several minutes, she bottomed out.

I pulled her down to me, kissing her with all the passion in my soul. Tears hit my cheeks as she met passion with passion. Her hips started moving, grinding. Brenda raised up, placing her hands on my chest. She closed her eyes, her lips parted. The excess lube squished between us.

I grasped her hips, "Slow down a little. Let's make this last."

She smiled down at me, "Agreed."

I reached up and cupped her small breasts, gently pinching her erect nipples. Her vagina gripped me, pulling me with her hip motion. Her sexual expertise evident. Brenda's grinding practiced and professional. She looked down at me with a look of pure love.

We were coupled together for ten, fifteen minutes when she collapsed onto me. My erection still buried deep, "I need a rest." She laid her head on my chest, "Looking back on my slutty days, no one ever cared for me like this. You and Bradley ..." Tears flowed onto my chest, "So kind and loving."

After several minutes, Brenda sat up again. Her hip motion began again, then stopped, "More lube needed."

She pulled off me and covered my cock in KY. She pressed me home with a groan, "God, how I love that feeling. I should have asked you to be my lover years ago."

She rode me for another ten minutes, then climbed off. "Back in the chair Mister Man. Time for me to finish you off."

As I stood, I pulled her into a hug, my erection pressed between us. I lifted her chin and kissed her again.

I sat down and she grabbed several tissues, wiping the lube from my cock. "Feet up!"

I obeyed, placing my feet on the desk again as Brenda settled between my legs. She pulled the cock ring off and began kissing and licking me. She looked up at me. Tongue twirling around the head. Finger probing my ass. Gentle sucks, then harder. Soon full blown face fucking as she took most of my shaft into her mouth.

A finger probed my anus. She rubbed my prostate and the orgasmic cliff came rushing at me, "Oh god, Brenda! I'm cumming!"

She just held the head of my cock in her mouth as she continued the prostate massage. Her eyes locked in on mine. I cupped her cheek as I felt my cock explode. An audible gulping sound came from Brenda's throat as she greedily swallowed my load. I let loose three shots, then she started milking my shaft.

"Mmmm. Mmmm. Oh, that's wonderful." She milked me until she devoured every drop.

I pulled her up to me and she straddled my lap. She wrapped her arms around my head. I kissed her, tasting my saltiness on her tongue.

I was still hard and she pressed my cock into her pussy, "Don't move. I want to feel you inside one last time."

After several minutes of kissing, Brenda said, "Thank you Will. You've made an old woman very happy."

"You're welcome. The pleasure was all mine."

She smiled, "And mine."

Brenda stood and pulled on her sundress, slipping into her flats. She stepped over and took my hands as I stood there naked, "I don't know if I will be able to communicate with you again. I don't think I'll be able to make it through Commencement without bawling my head off so I'm not going. I plan on giving the exams, submitting my grades, and then I'll be driving west. I won't see you again."

"I understand."

She placed her arms around my neck and softly kissed me, "I love you Will. I'm so blessed to have your friendship." She kissed me again, "Please don't say anything. Let me treasure this moment. A moment of pure love and joy."

Brenda kissed me again, pressing her tongue into my mouth. We stood there necking for several minutes. Then she turned and ran. I moved to my window and watched her cross the front yard of our building. When she got to her car, she turned and waved to me, then drove off. That was the last time I ever saw her.

*****

When her time came on July 5th, I stopped what I was doing and thought about Brenda, offering a silent prayer. I'd be lying if I said I didn't shed a couple of tears over her loss. The next day I received a large envelope in the mail. It contained an advance copy of Brenda's obituary. In the 'survived by' portion she listed me as her 'dear friend William'.