She was my boss when I was in high school. She was a very flirtatious and sexy woman about whom I fantasized daily. She was tall – about 5’9″ – and very well endowed with huge DD tits. She had long firey red hair and she knew how to get whatever she wanted out of a man.
I once came back to work to pick up something I’d left that day. As I walked in through the back door to the clothing store with my
current girlfriend Sarah, I realized that Samantha’s car was still outside. I started to yell out that I was coming in when I heard a loud moan from the front. We snuck up to the doorway leading from the back of the store and peeked outside.
Samantha was lying on the couch next to the dressing rooms with her head held back in ecstacy. She was wearing a short black skirt with black lace stockings and towering heels. She had lost her top and she had on a black lacy bra that was halfway off revealing one of her huge DD tits. Some guy I’d never seen before was kneeling down in front of her and he was eating her out for all that he was worth. Anyone who was walking down the street could have stopped and watched but she
knew that there was no one out on this side of town after 9p or so.
Sarah gasped slightly and I cupped my hand over her mouth. I whispered to her, “Shhh… If you want to watch we have to be dead silent!” She nodded in agreement as I turned back around to look at this spectacle.
While I was turned away, Samantha had turned over and placed one knee on the sofa and slid the other leg as far out as she could. The mystery man dropped his pants and slowly slid inside her as she said in the most cock-trembling voice I’d ever heard, “C’mon boy! Don’t you want to fuck tha boss??? Huh?!? Fuck me hard! Make me SCREAM!!!”
I shook my head and moaned approvingly as I watched this game play out. It was then that I noticed Sarah was pulling down my shorts with one hand as she reached in to pull out my cock with the other, sliding it easily into her warm mouth. I sighed as she began to suck my cock with a fury she never had displayed before. Samantha’s loud moaning and commanding tone had apparently been too much for Sarah to resist. As Samantha screamed for him to, “Fuck her HARDER! HARDER!!!!”, Sarah could take no more.
She pulled down her thong and bent over, as she was wearing a short flimsy skirt. As I began to pound her from behind, she grabbed a pillow and moaned into it so as to not attract the attention of the happy couple
just 60 feet away. She came quickly, squeezing me with short, quick contractions and then whipped around, taking me back into her mouth. I came a minute later as Samantha was screaming, “Yes… Yes… YES!!!” and
Sarah swallowed it all with a devilish smile on her face.
We left quickly and went to the party we had initially been going to before we got side-tracked at work. After an hour there, we couldn’t take it anymore and slipped off to the poolhouse for a little while before heading back to Sarah’s Aunt’s house to have some fun. The whole time I was fucking my cute little girlfriend, however, I was thinking about the unbelievable woman we had seen before and how much I wanted her to tell me to fuck her senseless.
Fast forward ten years…
I had just finished getting ready to go out to dinner. I was excited because Samantha, my old boss, was coming over to meet me. I hadn’t seen her since I graduated from high school and she moved away from my hometown. Upon hearing that she had moved to where I was living after college, I found her number and called her up. She was thrilled to hear
from me and especially since she had just moved into the area and knew no one.
I thought about that night Sarah and I watched her completely devour that guy in the store and my cock twitched in excitement. I would have done anything in the world to have had her that night and I was secretly hoping that she would show up and seduce me that night. Of course, I didn’t think it would happen, but it was a fun fantasy to hold
She was always flirtatious and she flashed me once when I walked in on her changing in the back of the store. She laughed and said, “What do ya think of these?!?” and showed me those gorgeous tits of hers for a few seconds before licking her lips and shutting the door while laughing hysterically. She used to grab my ass when we were alone in the store
before closing and make suggestive comments about us “Going away somewhere together.” She used to slither up to me and whisper in my ear, “No one will ever know…” as she knew that it drove me wild. She would laugh when my cock would grow semi-hard simply from her breathing lightly in my ear and I blushed with embarrassment.
I was just looking forward to seeing her again and enjoying a nice evening out. Thoughts of her huge breasts heaving as she rode me were interrupted as the doorbell rang. I cursed silently as I tried to hide
the slight bulge in my slacks. “Think un-sexy thoughts… Think big, bloated, nasty…”, I thought as I opened the door.
She squealed with delight as she saw me and stepped forward to give me a huge hug. I hugged her close and enjoyed the moment. I invited her in and she ran inside as she apologized profusely, “I’m so sorry – I ran
late at work and have to change here, is that OK?”
I surveyed the see-through white blouse that had one too many buttons undone and the tight blue jeans and replied, “Of course. This place isn’t too fancy, so whatever you want to wear.”
“OK… I’ve got something I think you’ll like”, she said as she winked and ran to the back to change.
I heaved a huge sigh and sat down on the couch to relax. I opened a bottle of wine and poured two small glasses as our reservation was not for another hour. I tried to keep my mind from racing with thoughts about Samantha and the way she used to smell and walk and slither and…
“Whew…”, I thought to myself as I leaned back on the sofa. “I’ll embarass myself for certain if I let my mind go like that.” I heard the bedroom door open and close and then the unmistakable clicking of heels on the tile hallway as Samantha walked towards the living room.
“I hope you’re not too upset about me being late”, she breathed as she came around the corner.
She was simply stunning. She wore a tight black dress with a fairly long slit up one side that showed off a lot of cleavage. I gulped as I peered downward and saw the strappy 3 1/2″ black heels and sexy silk
stockings she had slid into. She was also wearing a pair of reflective, metallic sunglasses – the effect was chilling.
“O-o-o-o-f-f-f-f c-c-c-ourse not – y-you look just… just… amazing.”
She threw her head back and laughed. “I KNEW you’d love this outfit. You used to get pretty hot and bothered when I’d tease you at work. It used to make my day that a young kid like yourself would get that worked up over me.”
I searched quickly for the right words. “Well, you were stunning then and even more so now. But… I’m not a kid anymore.”
She grinned mischeviously as she breathed, “I know. Wine and everything, huh? You must treat your girlfriend right…”
“Well, I’m not dating anyone right now. My last one wanted to get a little too serious. I just want to have some fun right now.”
“Oh, I’m sorry. I mean… you’re right. At your age you should be all about having fun. Serious stuff can wait for later”, she replied as she sat down beside me and crossed her legs seductively. “I know I’ve always just loved having fun.”
“I know…”, I said with a grin on my face.
“What is that supposed to mean, buster?”, she said with a smirk on her face.
“Oh, nothing. You used to tease me pretty good. And I… never mind.”
“You can’t do that. Share, share…”
“Do you remember Sarah?”
- she was a cutie.”
“Well, we came back to the store one night to pickup something I’d left that day. It was a little after 9p. As we cam
e in I heard something. I’d noticed that your car was still there and as we walked towards the
front of the store, I heard a… ummm… well, a moaning sound.”
Samantha gasped as I continued, “We snuck up to the curtain and peeked out. We saw you with some guy on the couch over past the counter. You were, ummm…, pretty busy.” I blushed as I remembered that night.
“Oh, my… You saw that?!? Oh… He was a friend of Larry’s who owned that store down the street. He came in to look at a suit as a favor to Larry and one thing led to… You didn’t say anything?”
My heart raced as I recollected, “Well, I couldn’t. I mean… I didn’t know what you would say. And Sarah… Well…”
“She watched, too?!?”
“Ummm… Yeah. Kind of. I mean…”
She licked her lips as she asked carefully, “What did you two do? Did you two make out right there?”
“More than that?”
“Well, she started giving me a blowjob and then she turned around and…”, as my voice trailed off.
“You guys fucked right there as you watched me? Are you serious?!?”
“Don’t be mad – we just got caught up in the moment.”
She smiled and leaned back on the couch as she ran her long, red nails across her cleavage. “Mad?!? Are you kidding? I’m impressed…”
I frowned as I asked her, “Impressed?!? What do you mean??”
“Well, I used to think you could do so much better than the girls you dated. You were just so shy. If I knew you were the type to fuck your girlfriend as you watched your boss fucking some guy 60 feet away, I wouldn’t have worried at all,” she said as her voice trailed off giggling. “I used to tease you to try to get you to come out of your shell.”
I grinned as I replied, “Well, if you knew half of what I used to do I don’t think you’d have worried at all. And if you knew what you used to do to me…”
“Oh, I knew. Believe me – I knew. I’m sorry if it bothered you but, to be honest with you, I just enjoyed it to death. Having a younger guy like you oogle me all the time was so flattering. It used to have a greater effect on me than you, I’ll bet.”
“I doubt that…”
“Oh, no. I’ll bet you it did. If you knew what I used to go home and do after teasing you all day”, she said as she licked her lips. “Mmmm, you were like the forbidden fruit.”
I swallowed hard as I replied, “Well. You look hotter today than I’ve ever seen you look. How forbidden can I be ten years later?”
She sat there, mouth barely agape for what seemed like an eternity. She then licked her lips, leaned towards me and whispered, “I guess you know that I have one son two years older than you.” I swallowed hard as she said breathlessly, “I guess it’s a good thing for you that I’ve fucked a couple of his friends, huh?”
With that she stood up and walked to the middle of the room. She slowly slid both straps of that tight black dress off of her shoulders and slid it down until it barely covered her huge nipples. She turned to
face me. “Can you give me a hand?”, she said in the most sultry voice I’d ever heard.
I stood up and walked behind her, trembling with excitement. The moment I’d waited for all these years was at hand and I didn’t want
to even blink…