First Time For Everything Pt. 02

I was anxious to get back at college in August. My girlfriend, Tilly, had found another guy to satisfy her urges and it wasn't until late September I hooked up with Marilyn. She was full figured, not fat, but had some 'meat on her' as they say. Marilyn had the most beautiful face I had ever seen and tits to match. I became addicted to sucking on her nipples which only electrified her lust for my cock.

Marilyn didn't need me wearing a condom. She loved the rush of cum pouring in her pussy and I would eat her out when we had finished. It never was a problem. I had already tasted my cum with Delores and I was used to doing it. Marilyn thought I was a pervert but that was what she loved about me. We must have screwed three or four time a week when I knew her. After Thanksgiving, we both moved on to other adventures.

The first time I was involved in a threesome was when Delores suggested it during winter break. She asked me to help her put up Christmas lights on the house and do some decorating inside. We took time out for an afternoon fuck and then continued to do more decorating. We ended the day in the holiday spirit with a second, lengthier fuck that day.

"Have you had a threesome, Fly?" she asked. "You know, with two girls?"

"Not really. I did my girlfriend, Marilyn, in the morning then fucked a different girl that same night at a fraternity party."

"No, I mean with two girls at the same time."

"I can't say I've had that opportunity."

"Well there is a first time for everything. My friend Billie Shadhorn would like to meet you. She's out of town now with her husband but maybe you can meet her when you come home for spring break. She's such a good friend and her husband, Mike, only wants sex once a week, if she's lucky. That's why I go over to her place and help her get off. You know, Fly, in ways that only women can do for each other."

"I didn't know you were a lesbian," I told her.

"I'm not. It's just a favor to a friend. I guess you could call me bi, like in bisexual but I like men the best."

"I'd like to do what I can for your friend, Billie. Just give me the time and day."

My studies were going well. Marilyn and I were still together, and she kept me contented, but I was curious about Billie. What did she look like? How old was she? Was she going to be as good a fuck as Delores?

When I was home for spring break, I met Billie for the first time. Billie was an adorable petite woman, "five foot two, eyes of blue" like the old song says. She was born in the Ukraine and met Mike while he was in the military. She looked like a teenager and had the most hypnotizing accent. The three of us met at her house for a get acquainted dinner. Mike her husband was also there and did the cooking.

"Mike is taking cooking classes and likes to show off his culinary skills." Billie explained.

Mike came over to ask Delores, "How do you know Flynn?"

"Oh, when he is home from college, he does some favors for us. I thought he would like to meet you and maybe do some work for you and Billie this summer." Of course, everyone but Mike knew what favors I was providing.

"How nice. We might have some odd jobs for Flynn this summer," Mike replied.

Dinner was close to being a gourmet meal. I complimented Mike on an excellent dinner. On the way home Delores said we would get together at the Spring Inn Motel on the Wednesday before going back to college. The Spring Inn was a sleezy motel on the edge of town where they always asked if you were paying by the hour or for the night. "Will Mike join us?" I asked.

Delores laughed and said, "That's very unlikely!"

The week dragged on. I did some work with my dad at his office. I tried to image what it would be like having sex with two women. As it turned out, my imagination didn't come close to the experience.

To begin with, the women were already naked in bed pleasuring each other when I arrived. They hardly noticed when I walked in the door. It was the first time I had seen two women have sex together in person. I just sat down on a chair and watched.

Occasionally they switched positions, Billie on Delores, then Delores on Billie. When Delores noticed me, she waved she said "Hi" then turned to do a sixty-nine with Billie. I pulled off my clothes and let my cock go free. If I stroked it, it would go off like a firecracker, so I just squeezed it hard trying to hold back.

Eventually the women came up for air and asked me to join them. I started sucking Billie's small but erect nipples while Delores continued to eat her out. That was followed by my attention to Delores's glorious tits while Billie took me in her mouth.

I'm afraid to admit I had no control when both women were licking and sucking my cock and balls, I exploded in their faces. "My god, Fly, you put on quite a show there," Billie said. "Lick our faces while you calm down."

After being with Marilyn, tasting my own cum came naturally to me and the women loved it. Billie rolled out of bed and said, "Let's have a glass of the Russian vodka I brought back from the Ukraine. Do you want it on the rocks, Fly or straight up?"

"Straight up is fine, Billie."

"That's the way I like my men," she said.

"How's that?" I asked.

Billie winked and said, "Straight up,"

The vodka was strong, and it made me relax and a little dizzy. I was ready to try anything the women wanted. It took me a little more than a half hour to recover from my first ejaculation. Delores could see my cock rising and came over to me to hold it. "Billie, don't you think Fly has a lovely cock?"

"I agree, Delores. I only wish he could cum inside me like he did in our faces."

"Oh, I don't think you will be disappointed. He's got lot more in reserve." And I did.

I fucked them both for hours. The first time I finished inside Billie and she was so grateful. The next time I gave a load in Delores' mouth and she shared it with Billie. The time had gone by quickly and it was dark when we all went home. My first time in a threesome went well, I thought.

Billie and I got together in her home before I returned to college that spring. I would return in the summer for another threesome and more time with Billie and when Delores needed a friend. The last time Billie and I were alone together, she said, "I want to have your baby. Mike would never know the difference." I would know the difference and never had sex with her again.

Marilyn and I broke up at the end of our junior year under similar circumstances. She wanted to get married. I told her I wasn't ready. That ended our relationship but not the last time I fucked her. That came late in my senior year.

My senior year flew by quickly. I had several job offerings after graduation but promised my dad I'd work for him at least for a year. I wasn't at a loss for girls to fuck after Marilyn. The expectation on every date was to have sex even if it was a first date. So, I dated a lot of different girls and was rewarded most of the time.

Before leaving campus life as a senior, my fraternity brothers organized a bachelor party for one of the brothers who was getting married. He and his girlfriend already had one child with a second one on the way. The couple decided to make it legal. The party was to have entertainment including a whore who would service anyone willing to pay. The bachelor would be first and free, and he had to do it in front of us. He was game although nervous.

"What if I can't get it up?" he complained. We assured him the whore would help and made sure he was relaxed with a couple shots of whiskey. The surprise wasn't that the fraternity had hired a whore. The surprise was who the whore was. At somewhere after ten that night, in walked my former girlfriend Marilyn. She wore a simple sexy dress wearing too much makeup while showing plenty of cleavage and legs. She looked so slutty I hardly recognized her. She wore no bra and I suspected no panties because that was how she liked to dress on our dates. The brothers hooted and hollered their approval as she tapped each of us seductively in our crotch. When she reached me, she put one arm around my neck, and another hand firmly held my balls. She gave me a wet sloppy kiss and whispered, "I've missed this, Fly." Marilyn was quite a good performer but that was only a start.

Her first act was to strip. There wasn't a lot to take off. In the process she lowered her top to show the boys her tits, then raised her dress to expose her shaved pussy. We all applauded with one boisterous brother demanding she spread her legs. Marilyn sat on a chair and obliged. Another guy yelled out, "Finger your pussy!" She did that too. "The fraternity social chairman said, "Hal, where's Hal? She ready for you Hal. Get over here and fuck this whore."

Hal had a great cock but it wasn't straight and stiff, too rubbery for a proper fucking. Marilyn took him in her mouth and worked on him for a minute or two but when he was ready and at full strength, the place was ablaze with ruckus filthy comments.

Hal's first thrust was tentative followed by faster and harder strokes. He wasn't going to disappoint his buddies and fucked Marilyn for a good five minutes. He came on her face and in her mouth with a sudden burst to the delight of everyone.

"Your bride is going to love you Hal," someone yelled.

"She already has!" he yelled back.

Our president announced that Cassandra (OMG, Marilyn changed her name), Cassandra was giving a quantity discount to the fraternity. For a pussy fuck with condom, it's $50, bareback, $100. Anal is seventy but only with condoms. I stood in line with the others. Ordinarily I wouldn't pay fifty dollars especially to a girl that gave it to me free, but I was so worked up, I paid the price. It was my first gangbang.

Leaving college behind after the best four years of my life to join my dad in the impart/export business was painful. I had other job opportunities but had made a one-year commitment to work with my dad, learning the business and deciding if it was what I wanted for a career. He gave me a title, "Vice-President" but there were only two of us and our secretary Sheila.

I liked Sheila. She was pretty and had a great sense of humor. Sheila was my mom's age, a young looking forty-six. She had been married, had a granddaughter, and was divorced. We got in the habit of playfully flirting with each other, often with sexual innuendos.

When business was slow and dad wasn't around, we would jokingly flirt. We had a private competition of who could tell the dirtiest joke. Sheila made our office a lively place and fun place to work. She'd tease me and say, "A lady might want a guy like you on her bucket list." I assured her I'd always be available to jump in her bucket. She joked I had to grow up first before I was worthy of her bucket. So I told her that I had grown up in college and sometimes talk about my sex life there. Of course, I mentioned Marilyn and said she was my girlfriend with benefits until she became Cassandra the whore.

Sheila loved the Cassandra story and never got tired of hearing about my college years. She even told me a little about her history that included a few one-night stands but no permanent boyfriend until she got married and had a child. Sheila even admitted that her sex life with Bernie, her ex, wasn't at all what she had hoped for. "He just wasn't all that attentive. A girl has an itch that needs to be scratched more than once a week, if you know what I mean, Flynn."

I knew what she meant. "Are you dating now?" I asked.

"A little. I have a few male friends but nothing serious. At my age, you can't be choosy. I still think of myself as a young chick and fantasize about hooking up with hunks like you, but it hasn't happened yet." With that she gave me a seductive grin. It was my cue. I wanted to be at the top of her bucket list.

From then on, I greeted her each morning by saying, "Get any itches scratched last night?" She just gave me the finger until the week my parents went on vacation. It was the first time I was in charge of the office.

"Get any itches scratched last night, Sheila?" I asked with a grin on a Monday morning. She didn't produce the middle finger salute but said, "Yes and I had to do it myself. How about you?"

"About the same," I said, and we tried to get back at work.

On the following day I greeted her with the itch question. She said nothing at first when she sat on the edge of her desk and spread her legs. "I thought you could do it for me."

I was down on her in seconds. Her pussy was nicely trimmed but not bald. It wasn't a bush but like a crewcut. Sheila was wet in minutes, and her orgasms came early and often.

"You're good at that, Fly. You make a woman feel like she's floating on air. Tomorrow, maybe I can return the favor."

Wednesday began like before but this time she slid her top off to show me her tits then unzipped my pants. Sheila was a great cocksucker and was among the top three women I knew who could deep throat without gagging. I would like to have lasted longer but I blasted her mouth with a generous supply of cum that disappeared in one gulp.

"That was great, Fly." She said. "I can see why you've had your way with the girls. You have such a nice handsome cock." It was the first time anyone had called my dick handsome. Big, thick, and hard, but never handsome.

Thursday I was over the top horny and couldn't wait to get to the office. She wasn't there and called in sick. Thankfully, Sheila was back at work on Friday. I fucked her on her desktop. It surprised me that a woman going on fifty could be that tight. I told her that she had a cunt of a teenager.

"Oh my god, Flynn, I've wanted you ever since you began working here."

"Were you disappointed?" I asked.

"Not by a long shot. 'You do that voodoo that you do so well.' You know, maybe we can scratch each other's back again sometime." A song lyric followed by and interesting euphemism all at one time. Sheila wasn't just sexy but clever as well.

I said, "Yes, but next time we need to find a more romantic setting."

She giggled a little girl's giggle and said, "My place or yours?" knowing that I didn't have a place of my own.

It was at her place on a Saturday night. She wore a sexy kimono that was hanging loosely around her body barely held together with a sash. Both the top and bottom of the gown were open showing cleavage and her upper thighs. There was no doubt that we would continue where we left off at the office.

Sheila brought each of us a glass of wine and sat shoulder to shoulder, hip to hip next to me. "I've got a confession to make, Fly," she began. "The truth is, I wasn't sick this week. I had a sleep-over with a friend of mine. He's an older man that I've known for a couple of months but all I could think of the whole time was your beautiful cock. I'm so lucky to be working for two sexy men."

"Have you had sex with my dad?"

For the first time, I saw her blush. "No, Flynn, but I tried seducing him one evening when your mom was away on a lady's weekend. She wanted me to join them, but I had other plans. I was thinking about your father, so I asked him to dinner. I wore this kimono thinking he would get the picture. "Do you think it's sexy, Flynn?"

"On you it's very sexy, Sheila."

"Thanks. Well when you dad was here for dinner and he didn't make a move on me, I finally said, 'I want you Sid.' He looked embarrassed and said he wanted me too but would have to fire me if we had sex together. I needed the job so all I got was a sweet kiss. I mean your dad is a sweet guy and all that, but I wanted more than dinner and a kiss. Then you came along, and it took forever to get your attention."

"I was paying attention, Sheila. I just didn't know how to go about getting you in bed."

"Speaking of bed, Fly, don't you think it's past bedtime?"

She undid the ribbon around her kimono and let it drop to the floor giving me a full view of her naked body for the first time. She had kept herself in great shape and her sizeable tits were firm and desirable. We 'scratched each other's back' for the rest of the night.

Over the next month Sheila and I got together for do overs until we got it right. I thought we got it right the first night, but she insisted that we had to keep working at it. She was the first grandmother that I had screwed and enjoyed every moment.

Together, work became a struggle as we kept eyeing each other for most of the day. The hardest part for me was keeping my hands off her tits. It couldn't continue and it didn't. It ended suddenly and unexpectedly. Dad came to my desk and said, "Sheila has given us notice."

"She what?" I asked.

"She quit."

"Why?"

"She said it has become too difficult to work here."

"Did she say why?"

"No, and I asked."

"She gave me that wink Sheila gives us when she is keeping a secret. Do you have anything to do with this?"

"I hope not."

"Flynn, have you been fucking her?"

I looked down at my desk and the answer wasn't there.

"Well, have you?"

"Yes, well yes. You know how she is dad."

"I know how she is, but good employees don't grow on trees. It's going to be hard to replace someone as good as Sheila. She was the best secretary I've ever had."

"I'm sorry dad. I didn't think it would turn out this way."

"Of course you didn't. Anyway, Sheila gave us the name of a girl who is looking for a job. The girl's name is Petula. Apparently, she graduated from high school last year. She will be here tomorrow for an interview. And please, don't hit on her. Maybe I need to do the interview."

Dad hired Petula on a two-week trial basis. She was nineteen and attractive in an exotic way. She had ear piercings and one on her left eyebrow. Petula said her hair was cut short because she didn't want to manage it all day. She dressed neatly but not fashionably. Her clothes followed the same simplicity theme as her hair. Sometimes she looked as much like a boy as a girl. What attracted me to her was her quirky personality. Petula had a breezy carefree way about her.

I did my best to follow dad's advice and work with her in a professional platonic manner. However, that wasn't easy since I was the one to train her and show her the ropes. Although she wore little makeup, Petula wore the most alluring perfume that I couldn't resist.

We hired Petula after the two week trial because she was adept at the computer, had a great phone presence, and she managed the shipping flawlessly. Day by day the two of us got closer and closer, colleagues at first, then friends, then one day I drove her home.

"Thanks for the ride, Flynn. Normally I take public transportation but today the weather was so bad I had to ask you for this favor. Do you mind if I ask you something else?"

"No, go ahead."

"You're not gay, are you?"

I chuckled before saying, "Far from it."

"Well, why haven't you hit on me. I've been working with you for over a month and you haven't made a pass at me even once. You never even gave me a hint that you liked me. A girl likes to know she is admired by a man."

"I do like you, Petula but it's a long story."

"I want to hear it."

I turned into a mall parking lot and said, "It's like this ...," and told her about my relationship with Sheila. She showed no sign of alarm or embarrassment, then she said, "The reason I took this job was because I liked you and thought we might be friends, you know, outside the office."

"Friends. You mean friends like on social media."

"No, friends like you were with Sheila. Look, Fly, I like the job and the money is good, but I'm not going to do it forever. When I've saved enough, I'm going to college to get a teaching degree. In the meantime, while I'm working, I want to date and have fun."

"Don't you have a boyfriend?"

"I've had lots of boyfriends, but they are all away at college." She put her hand on my lap and kissed me, then she said, "Take me home now. I've said too much."