Category: Group Sex Stories

My Big Oops

by mdiver©

An email mistake leads to a new beginning

Author's note: This short story is based on an actual event as told to me by a reader. I'm hoping, based on how this story goes, she will provide more details for a sequel.

My name is Sheila and this is my story. I'm still in shock that it happened at all, least of all to me. It brings to mind the old saying that truth is stranger than fiction.

First, here is a brief history about me. I live in LA and work in the investment department of a large bank. I'm 5' 6", fairly slim and what gets me noticed by men is my breast size. To put it bluntly, I have big tits as in a size D cup. In my younger days, especially during high school, I was pretty self-conscious about them. Once I entered the working world, I found them to be a great asset and it was fun to use them to my advantage. It's amusing to follow the gazes of men as they drift over my face and settle on my cleavage.

I never lacked for dates in high school and I lost my virginity right after graduation. My boyfriend at the time and I had planned the occasion and even though I was eager for it to happen, I was still anxious and a bit nervous. We did our share of fondling in the back seat and even partially undressed each other. Soon our dates were getting more and more heated. I wanted it to be a romantic experience as well as to satisfy my curiosity and lust. Granted I didn't experience an orgasm, however, I really enjoyed the whole experience. From that point on, we engaged in a lot of sexual play. I knew that I enjoyed sex and wanted to get as much as I could. I had a good looking, well equipped boyfriend who felt the same way. We experimented with many positions and venues. But alas, our distance apart at college made our romance difficult so we decided to go our separate ways.

At college, God knows it was easy to find guys who were eager to fuck. However, I was on a scholarship and my grades were more important. Also, they seemed rather sophomoric and not many were worth my time. I learned that masturbation felt almost as good and kept me from getting involved. I wasn't ready to fall in love again and didn't need the complication.

I met my current boyfriend, Jim, at a continuing education seminar for financial analysts. It was one of those chance encounters that brought us together. Originally, he hadn't planned to attend but a last minute cancellation made it possible. What got my attention was that we both preferred to sit in the back row so we could stand up occasionally. I was immediately attracted to him. He was much taller than me, incredibly handsome with dark wavy hair, hazel eyes, a nice body, and he came across as nerdy as me. We chatted over lunch and agreed to continue at dinner that evening. From there, the relationship blossomed.

Even though I was smitten with his intelligence and our mutual interests, I felt a lusty heat every time I was near him. I wanted our relationship to work so I was careful not to rush anything, but I could hardly wait for him to put a move on me. I thought he felt the same about me so was confused when he never initiated anything. My pussy was aching for some attention and eager to resume a sexual relationship, so I decided I would have to be the one to seduce him.

Much to my surprise, that turned out to be pretty easy. On our next date, we had some nice long and wet kisses with lots of tongue. There had been no exploring with our hands which I found to be very difficult. So, as planned, this time I slid my hand up his thigh, hoping he would get the idea that I wanted to feel more of him.

I tried to convey my approval with my kiss and it must have worked because he slid his hand under my blouse and unhooked my bra. Within minutes, my top and bra were on the floor. I'm sure I let out a soft sigh as his large hands cupped and caressed my breasts. My nipples were hard and sensitive, responding to every touch. With each brush of his tongue across them, I could feel the tension rise deep between my legs. It had been a while since I had felt sexual desire like this and I was relishing every moment.

He was driving me crazy with desire. With some maneuvering, I was able to get into a position where I could place my hand in his crouch and feel his hard cock. Even though his jeans were in the way, it felt wonderful in my hand and I was eager to have it in my cunt and mouth.

Lust was raging as I started to remove his clothes. He even helped by unfastening his pants so I could pull them down. Soon we were both down to our underpants. I was glad I had planned ahead and had worn my nice black thong. His briefs gave a lovely outline of a very hard and beautiful cock. I was torn between wanting to take the time to admire what was before me or to continue. I slowly pulled the briefs that were confining his lovely erection. When it sprang out, all I wanted was to put the head in my mouth and savor the taste.

His precum was like nectar and I could feel my pussy throb. My hands explored his shaft and balls. After a few strokes, I looked up and pleaded, "Don't make me wait much longer."

He pulled me to the floor and slowly removed my wet thong. He looked at my bare pussy and said with a smile, "How very lovely."

I wanted to reach over and pull his cock into my cunt but Jim had other ideas. He kissed around my pussy, slid his tongue down my labia and fucked my cunt with his tongue. He soon had my heart pounding and I was breathing hard as I was building to my climax. When his fingers began their magic on my swollen clit, my body shook as my orgasm rolled through me like a wave.

Before I could catch my breath, Jim moved his tongue directly to my clit. It was only a matter of a few seconds before I felt my second climax. This climax was even more intense. I swear I saw stars as an electric shock wave shot through my body. At that moment I decided I had found a keeper.

He leaned down and as we kissed, I licked my cum from around his mouth. I reached down and took his dick in my hand and gently pushed it down between my legs until the head was pushing against my wet cunt.

Slowly he began to fill me. Every stroke was short yet his penetration went deeper until he could go no further. I crossed my legs over his back to hold him in place while I squeezed my vagina muscles around his wonderful member.

Our eyes met and I gave him a big smile as my way of telling him how glorious I felt. He leaned down and gently kissed my forehead, then my eyes, then my neck, and then my mouth. After a few moments of bliss, I spread my legs wide and he began his slow, long strokes. My breathing quickened to panting as his thrusting became faster and harder. I was on the edge of another climax and when he pinched my nipples hard, my body stiffened and then shuddered with another magnificent orgasm.

He didn't stop his hard and fast pounding. I could hardly catch my breath after the next climax and fortunately he stopped. I crossed my legs over his, not only to make sure he stopped, but to pull his glorious cock deep into my cunt. I loved the way it felt and I squeezed my muscles as hard as I could around it.

I looked into his eyes and said, "That was incredible."

"My pleasure."

"You didn't cum."

He shook his head and I said with a sly grin, "I can fix that."

Slowing we pulled apart. With him on the floor, I knelt between his legs. How lovely his cock looked; long and hard and wet with my cum.

I took his beautiful dick in my mouth and licked it clean. His balls deserved no less the same attention and were also were also gently and carefully cleaned. His moans of delight were music to my ears as I was eager to replace the taste of my cum with his.

I placed my lips around his hard cock and slowly took it deep in my mouth.

"Oh baby, that feels incredible," he moaned.

I gradually moved up until my lips stopped at the base of the crown and I placed my hand around his shaft, locking it against my lips. I loved how it filled my hand and mouth, not to mention my cunt a few minutes ago. My pumping started slowly and as I increased in speed, he pushed his hips upward against my down strokes. It had been a long time since I had my mouth fucked like this and I was in sensual heaven.

I reached down and gently held his balls and that was all it took to push him over the edge. I felt them tighten and then his whole body went rigid. Suddenly he thrusted his hips up and I felt his cum pulse through my hand and into my mouth. The warm liquid shot hard and it seemed endless. I swallowed as fast as I could without stopping my pumping. Finally, he relaxed and I continued milking every drop from his perfect love tool.

That was the beginning of our wonderful relationship. We were a good match intellectually and physically. We really enjoyed expanding our sexual play with just about everything two people can imagine. There isn't anything we wouldn't or didn't do for each other. One of the things we enjoy is teasing each other with emails when we are at work, which gets me to the crux of this story. We really had fun sending pictures and naughty messages to each other.

One day while at work, I received an email from Jim that simply said how much he enjoyed our weekend adventure. I didn't respond immediately since I was busy with a client on the phone. My client started rambling so I decided to respond to Jim's email. While pretending to be listening to my client, I thought I clicked on Jim's email. I was feeling playful and I gave him a blow by blow, so to speak, accounting of how much I also enjoyed our road trip. My mind shifted to the fond memories. I told him how much I loved the way he played with my pussy during the drive and how nice to be driving down the road and having your man masturbate you at the same time. I loved the orgasms he gave me but I felt disappointed that I wasn't successful in reciprocating with a BJ. I gave him a pretty detailed description of what was in-store for him the next time.

I completed my call and hit send with a big smile on my face and slightly damp panties. Unfortunately, when I went to delete the original email, I discovered it was not from Jim but my boss. Being distracted and trying to multitask had turned into a disaster of the first order.

"Oh no!!!" I said loudly enough to get the attention of my surrounding co-workers once I discovered my error.

"Fuck...fuck...fuck" I kept repeating to myself, wondering just what the hell had happened and what my fate would be. My heart was racing, my hands were sweating, and suddenly an idea hit me. I would rush into my boss' office and tell her not to open my recent email. Happy with my decision, I pushed back my chair and as I stood, the phone rang.

In the movies the writers would milk that situation for all it's worth. This was not the movies and I feared the worse.

"Hello, this is Sheila," I said with as much confidence in my voice as I could muster.

"Yes Sheila, I need to see you in my office right now."

My heart went from the pit of my stomach to my throat. I've always been a good employee, surely she wouldn't fire me.

"Close the door and have a seat."

I took a deep breath and sat down. I put on my brave face and looked straight at her.

"Interesting email you just sent me. Were you really planning to do all these things to me?"

There was no smile on her face. Oh shit, I thought.

"I can explain," I blurted out. "My boyfriend and I like to ... ah, tease each other and it was all in fun, meant for him."

"On company time?"

"It's usually during our lunch break but I got to thinking about the trip and well, ah, I got carried away." I'm sure my face was beet red by now.

"It must have been quite a trip."

I sat there waiting for the sky to fall when she got up, came around her desk and sat in the chair next to me.

"Tell me more about the drive and what happened."

I was shocked and I'm sure the surprise was evident on my face.

She smiled and said, "Relax Sheila. I'm intrigued by your adventure. My husband and I have done virtually the same things on road trips."

It wasn't long and we were laughing and sharing stories about our sex life. I couldn't believe my change in fortune. I got a big kick from the part where she said that she and her husband test drove several cars before getting the one they have based on her ability to give him a good blow job. "Damn consoles," she said.

"My husband is really going to enjoy our little conversation tonight. This is as juicy as some of the stories we read each other except its real which makes it all the more exciting."

Before I left, she invited my boyfriend and me to her place for a cookout. We settled on this Saturday. "We also have a hot tub," she said with a mischievous grin.

The rest of the day went like a breeze. Such a heavy load was lifted from my mind and I had to pinch myself to remind me that it wasn't a dream. I was excited about telling Jim tonight about how my "oops" turned out to be a whole new adventure.

That night, I replayed the whole story about the errant email with him. He sat there, without interrupting, with a look of astonishment on his face. When I completed my narrative, he sat there quietly and I could see the gears turning in his mind. After a few minutes, he looked at me with a big grin and said, "Do you think your boss, Sandy, has more in mind for us this weekend?"

That gave me pause, "Like what?"

"Maybe something like a swap? You with Brian and Sandy with me?"

It was my turn to grin. "Oh my. I hadn't thought of that. Let's say that happened. How would you feel about it?"

Jim pulled me into his lap and gave me a kiss. "You know, sweetheart, I'd do anything with you and if it's ok with you, then It's ok with me. Truthfully, the idea of watching someone fuck you or see you suck a cock I think is exciting and erotic.

I gave my wonderful guy a big kiss. "I was hoping you'd say that. Sandy didn't say anything about this so I'll just follow her lead. My gut feeling is telling me you're correct."

That night after dinner, Jim cleared the table, then picked me up and put me on it. He quickly removed my clothes and soon had his face buried in my pussy. Between his fingering my cunt and licking my clit, I had so many orgasms that my body was shaking. I finally had to ask him to stop so I could recover.

"Thinking about what you told me got me so horny that I just wanted to taste your sweet pussy."

"Well I think I should do my part."

I quickly undressed him and lead him to the bedroom by his hard cock. I pushed him down onto the bed and then straddled him. My cunt was so wet it was dripping and it was easy to slide his beautiful cock inside. I rode and pumped him hard. I had a few more orgasms before I felt his hot semen shoot deep in me. I collapsed into his arms and we fantasized about what might happen this Saturday.

The next day when I arrived at work, I had an email from my boss. It simply said: We're going to lunch.

We slipped out of the office for what I expected to be an interesting lunch. Sandy picked a place that allowed us some privacy and served delicious salads.

We chatted a bit about telling the guys our story. I added, with some graphic details, the subsequent fun Jim and I shared. Sandy was all smiles and said she took Brian out to the car and gave him a BJ just like I wrote in the 'now infamous' email. Then she took him back to the bedroom and rode him hard just as I had done with Jim.

"We seem to have similar ideas about what to do with our men," she said with a big smile.

"And what they like to do with us," I responded. "I love being a slut for my guy. It's great how we both want to keep our sex lives exciting and erotic."

Sandy was quiet for a bit and I could see her mind at work. I had a strong feeling Jim's suspicions were correct and the Saturday's invitation was going to have an additional 'meat' course on the menu.

"Sheila" she said and then after a pause continued. "I'd like for you to right now to think of me, not as your boss, but as another woman just like you are with the sexual playfulness we have with our men."

"Ok," here it comes I thought.

"Brian and I like our sexual adventures, too. After our talk yesterday, we wondered if you and Jim might be up for a shared escapade, so to speak.

"What did you have in mind?"

"We could do a partner swap."

I could see the look of concern on her face. All kinds of things can go wrong at this point, but then could be a lot of fun and since Jim and I had agreed, I replied, "Sure. I think it would be fun."

"Don't you need to ask Jim?

"No. We were both hoping that might happen."

Sandy broke out into a huge grin and started laughing.

"Whew. That's a load off my mind."

"How shall we make this happen since it's not going to be exactly a surprise?"

Over the rest of the lunch, we discussed various ways we would have fun with the boys and formulated a plan.

When I got back to the office, I fired off an email to Jim that simply said, "You were right!!"

That evening I informed Jim that Sandy was all his to enjoy and she was looking forward to it. I wouldn't reveal any additional details except to say that I was looking forward to watching Sandy enjoy his beautiful cock.

The next few days flew by. Sandy and I were very professional and I'm sure no one suspected our little secret. Jim and I were excited with anticipation and I believe our love making was even more intense because of it.

Finally, we were on our way to make a fantasy a reality. Fortunately, Brian and Sandy weren't strangers. We had met them several times at various company events. Little did we suspect, however, that they had a more interesting private life.

We were greeted like old friends and ushered into their beautiful home. After the drinks were served, we took a tour of their home and garden. "Brian's a master gardener," Sandy announced proudly. Brian already had a bouquet of roses for us to take home. I must admit that I kept glancing at his crouch. The detailed discussions I had with Sandy had me thinking about his dick for several days. I also noticed Sandy glancing at Jim the same way. Already I was feeling heat between my legs.

Dinner really set the tone when Sandy said, "Since this whole thing started from a road trip, I'll tell you about our first time." What she told us was in very graphic detail of sexual play while driving. Including making sure the truckers could see Brian's hand rubbing Sandy's pussy or Sandy pulling up her shirt and flashing her tits at them. The more she talked, the more excited I became. I know I was practically panting and I think Jim was breathing hard.

Turnabout is fair play and I did my best to give a juicy and enticing accounting of our trip. I didn't try to top Sandy's story but I think it was pretty hot. I made it a point to watch Brian's face and he certainly was enjoying it. Since he was sitting next to me, I slid my hand over and placed it on his shorts; right on top of his boner. I heard him gasp as his eyes widened from the shock. He looked over and gave me a big grin. Later that night, Jim informed me that Sandy had her hand on his dick during most of my story.

We concluded dinner with a toast to finding new friends. Sandy and I told the boys to sit while we cleared the table. For us it was our cue for 'show time'. Our plan was simple; we would walk out of the house and into the hot tub, naked.

We stood in the tub and looked over to our lovers. "Aren't you boys going to join us?" Sandy said in a fake southern drawl. I don't think I've ever seen two men undress as fast as they did. Their hard dicks were waving in every direction as they literally ran to us.

When Brian stepped into the tub, I grabbed his member and put the head in my mouth. I swirled my tongue all around it and gave it a very wet kiss. His tool wasn't quite as long as Jim's but definitely thicker. Thinking about it in my cunt, made my pussy tingle. I glanced over and Sandy was bent over and Jim was taking her from behind. It looked good to me so I moved over to the side and joined her. Brian wasted no time rubbing his dick against my pussy and then slowly inserting his monster.

Category: Group Sex Stories