I went to school Monday knowing I had not seen or talked to Crystal in forty-eight hours since our hookup. I was looking forward to seeing her, but also a bit apprehensive about how we would now interact with each other.
When she arrived just before fourth period Crystal wore a giant smile and gave me a cute little wave, “Hi Mr. Haley!” She was dressed in a professional look with navy slacks, a red polo, and red heels. The slacks showed off her J-Lo Latina booty too.
She came up to my desk as the third-period students started packing up as the bell was about to ring for the passing period. “Miss Calderon, so nice to see you. Did you have a nice weekend?” I asked in a sarcastic tone.
“I did. I met a friend for wine tasting and we had a wonderful evening,” Crystal said with a twinkle in her eye.
The bell rang and the student filed out. When the last student left and the door closed behind her I looked at my new FWB and told her, “I had a wonderful time with you. I hope we can do it again sometime in the future.”
“We can, but I don’t want you to get attached to me, like, romantically. We’re friends, not boyfriend and girlfriend. You can’t fall for me like that. Do you understand?” she said.
I paused a moment and digested her words. I must have been a bit clingy or lovey-dovey Friday night. I need to pull back I reasoned. “Yes, I understand.”
Crystal continued, “I had a great time. I’d like to see you again in a week or two.”
Just then two students entered the room. We looked at each other and froze for a second.
“The ball is in your court. You’re welcome at my house any day, any time,” I whispered.
**
We didn’t speak about our play date the rest of the week keeping it all very professional. I, of course, would jackoff every day when I returned home thinking about our night together.
On Friday Miss Calderon entered my classroom and approached my desk, pulled out a piece of paper from a stack of papers she carried, and handed it to me. “Read this please,” she said.
At the top of the page were two short sentences. “Let’s repeat last weekend. Same place, same time.”
Without looking up I simply said, “This will work fine Miss Calderon. Did you finish grading the algebra tests?”
Crystal confirmed she had graded the tests and placed them on my desk. Then she took the paper from my hand, walked to the corner of the room, and ran it through the shredder.
The rest of the day went in slow motion as I could not wait to meet her for a bottle of wine and what I knew would be a wonderful evening.
**
I arrived at the winery first this time and I went inside and was going to order a bottle of wine and a small charcuterie board for us to share. Behind the tasting room bar was the same attractive woman from last week, Connie.
Connie was about my age, average height, a size eight-ten, and had a very cute face with light brown hair with a lot of golden highlights. As I approached, she smiled and said, “You were here last Friday with a beautiful young woman. You’re both teachers, right?”
I confirmed that Crystal and I are teachers and that we work together. “I’m Jay Haley, by the way. And you’re Connie, right?”
She laughed and pointed toward the name tag on her apron.
I ordered the same wine as last week and the charcuterie board and Connie said she’d bring it out back in about five minutes. I went to a side table, grabbed some napkins and forks, and poured two glasses of water. I headed outside and found our same table available, so I sat down.
Connie returned soon with my order and placed it on the bistro table. “Is your friend running late?” she inquired.
“I guess so. She hasn’t texted me,” I said.
Connie returned inside and about five minutes later Crystal walked out on the patio. “Sorry, I’m late. I was stuck behind two semi-trucks,” she said. Eyeing the snack board, “Oh, and a charcuterie board too? Wow, who are you trying to impress?” she said laughing.
I poured us our wine and we talked a bit about the week, the test scores, and a few students when Crystal excused herself to use the powder room. What seemed like forever, but was only ten minutes, she finally returned.
“It seems that you have made quite the impression on Miss Connie,” Crystal whispered, “She asked me several questions about you. And us. She thinks we’re flirting with each other. She said our sexual energy is noticeable.”
“Wait. What?” I stammered. “She thinks we’re dating?”
“She simply asked me if we’re a couple, but did mention, and I quote, ‘Our sexual energy is noticeable.’”
“And she asked about me?” I asked.
Crystal, giggling, “Yes. She said you’re handsome and wanted to know if you’re dating anyone. I told you that you are available. I hope that was ok.”
I had two lines of thought racing in my head. One, Connie is interested in me. Two, she noticed the sexual energy between Crystal and me.
“I guess we better stop being so flirty. God knows who else out here might know us or work for the school district,” I told Crystal. “And Connie said she’s interested in me?”
“Oh, Jay! Yes, she is interested in you,” she said. “And you are right, Connie is really cute. And she has a great body too. I’d sleep with her.”
I wasn’t sure if Crystal was fucking with me or was serious about wanting to get naked with Connie.
“Are you serious?” I asked. “Have you been with a woman before?”
Leaning towards me, Crystal whispered, “Yes. I’ve been with a woman. I’ve also had four threesomes. One with two guys.”
My jaw must have hit the ground by the look on Crystal’s face. She continued, “It’s 2022 Jay. All of my female friends have had threesomes and had girl-on-girl sex. It’s not all about love, it’s about sexual pleasure, having fun, and exploring new adventures.”
I sat back in my chair and stared out towards the vineyards trying to comprehend what my young twenty-three-year-old student teacher just told me. I sipped on my wine as I looked over the glass at Crystal imagining her with another woman.
“Honestly, I don’t know what to say. My mind is blown, but I am also very turned on by the thought of you with another woman. I’d love to watch that, and join in,” I said seriously.
Crystal smiled at me, “Maybe tonight’s the night. I’m going inside and I’ll flirt with Connie. Maybe she’d be interested.”
I laughed, “As if it’s that easy.”
Crystal got up from her chair and went inside. I couldn’t see the tasting bar, so I had no choice but to wait patiently. Almost ten minutes later here came both Connie and Crystal.
“Jay, I’ve invited Connie over for wine and pizza tonight. What’s your address?” Crystal said.
I looked at Connie who was grinning from ear to ear. “I’d love to see your house. Crystal says you have a pool too. I think the three of us would have a great time together,” she said as she winked at me.
“Nine-zero-six North Laurel Avenue,” I said. “Yellow house on the east side of the street. What time should we expect you?
“Probably about six,” Connie said. “By the time we clean up here and I go home to change, six or six-ten probably.”
“Wonderful,” I said. “I look forward to learning more about you.
“And I look forward to seeing more of you,” she said, again winking.
Crystal and Connie turned to face each other, they hugged, and then both kissed briefly on the lips.
“I’ll see you two about six. Back to work,” Connie said as she returned to the tasting room.
Crystal sat back down and looked at me. “See how simple that was?” she said. “You need to be more confident. Jay, you’re a good-looking forty-year-old man. You have a lot going for you. You own your home outright, solid career, a great pension, and tons of disposable income. Women look for those things in a partner. And you’re a stud in bed.”
“Thanks, Crystal. I needed that pep talk,” I told her. “But I also have two kids that I have a third of the time. I don’t know how attractive that is to most women in my age group.”
“Oh, Jay! Most women in your age group have kids too! Be positive!” she said.
“OK, can we talk about this next week? Let’s focus on tonight and Connie,” I said. “Obviously, I’ve never had a threesome.”
“Don’t worry about it. Just let it flow between the three of us, she said. Crystal continued, “She’s cute, I agree. If she and I are really connecting don’t be the guy who tries to break in and force your way into it. Always ask. And if you’re asked don’t be shy to tell someone “In five or ten minutes.” Be respectful and don’t be rude.”
Crystal and I finished our wine and strolled through the tasing room telling Connie we’d see her later. Crystal said she was going to make a stop at her apartment to get a few things since we were having a guest tonight.
I went home and chilled a bottle of Albarino (a Spanish white varietal) and opened a bottle of Zinfandel. I also moved a few beers from my garage fridge to the kitchen. I ordered two pizzas for delivery as well.
My mind was racing about the possibilities for tonight. I decided I’d take a quick shower to freshen up, and to make sure my balls were shaved. I put on fresh clothes and just a dab of cologne.
Crystal knocked on the front door and walked in shouting, “Jay, I’m here!”
As she rounded the corner into the kitchen I see she had the same thought I did, she was in fresh clothes too.
“Did you shower and change too?” I asked.
“Yes,” she said.
“And shave your sweet kitty?” I teased sarcastically.
“Yes. And I bet you shaved your balls, right?” she laughed.
“You know it. I’ll be honest, my fantasy is to be standing up and having you two suck my cock and balls at the same time, with one of you stroking my cock,” I confided.
Laughing, “You’ve been watching too much porn, Mr. Haley!”
Nodding in agreement, “True, but not this week. I’ve been jacking off thinking about last Friday. And Saturday morning,” I told Crystal.
I poured her a glass of wine and took her into my arms and kissed her passionately. My cock was already standing to attention like a soldier during an inspection from an Army General. I pressed my dick into her lower torso and thrusted my hips two times.
“Settle down. It’s going to be a long night. Remember what I told you. And don’t get too excited and rush through things. Enjoy yourself. Enjoy the experience of two women. And enjoy the sexual pleasure,” Crystal told me.
“For such a young woman you are very wise,” I said.
Crystal looked at me sheepishly, “I don’t tell many people this, and you have to promise to keep it to yourself, but my minor in college was Human Sexuality.”
“Really?” I said. “That explains a lot. Your wisdom, your attitude towards group sex, hooking up, etc.”
Just then there was a knock at the door, “Well, it’s either Connie or the pizza guy,” I told Crystal.
“Let me get it,” she said. I agreed and handed her a ten-dollar bill for the tip.
I could hear the conversation and it was our pizza delivery. And then I was a bit stunned. “For your tip, you have an option. You can have these ten bucks, or you can feel my tits,” Crystal said.
I moved from the kitchen island and stepped into the hallway so I could see the front door. There was about a seventeen or eighteen-year-old boy. Long greasy-looking hair underneath his pizza hat, acne, and average looking at best. A real nerd.
“Can I see your tits?” asked the pizza boy.
“Sure,” said Crystal. “And you can feel them too. This is your lucky day pizza boy!” With that, she pulled off her tank top exposing her lovely tits.
The kids’ eyes bugged out of his head like a cartoon, his jaw dropped, and he was speechless just staring at one of the best racks I’ve ever seen in my life. And what I’m pretty sure was the first time he’s seen real naked boobs.
“Go ahead and touch them,” she said. “Squeeze them softly.”
The kid did as he was directed. After the second squeeze Crystal told him, “Go ahead and lick and suck them.”
I thought the kid was going to pass out. He didn’t say a word and leaned down to first lick both breasts and then sucked each one.
Just then Connie pulled up and could see what was going on in the foyer. She seemed to race out of her car and up the walkway.
“What’s going on here?” she asked.
“Fulfilling the pizza boy’s wildest dreams,” said Crystal.
Laughing Connie said, “Well, let’s really give him a story to tell back at work,” as she removed her midriff tee.
Connie’s tits were fabulous. Bigger and fuller than Crystal’s, I guessed she was a 38-40 DD. Her areolas were huge, about two-and-a-half inches wide, and she had large dark nipples that reminded me of a Milk Dud candy in both size and color.
Crystal commanded the boy, “Go ahead and feel her tits just like you did mine. And then lick and suck on them.”
When the boy was done both girls were giggling, and I was enjoying the show from twenty feet down the hall. The poor kid stood there dumbfounded saying nothing.
“Are you a virgin?” asked Crystal.
The pizza boy looked at Crystal, then his eyes shifted to Connie, and then he noticed me in the background. He didn’t say a word for about five seconds.
“It’s ok,” said Crystal. “We were all virgins once. Are you still a virgin?” she asked again.
“Yes,” he mumbled.
“OK,” said Crystal. When we order a pizza next Friday you better be ready to fuck me. No jerking off for two or three days. Do you understand?”
“Yes,” he mumbled again.
“Good. You better get back to work. And don’t say a word about this to anyone. If you do, I’ll hear about it and you will not get to fuck me next week,” Crystal said sternly. “Now get out of here!”
The pizza boy turned and damn near sprinted for his piece of shit old Toyota Camry. As he pulled away from the curb both Connie and Crystal held their tits and giggled them for him. His eyes widened and he had a huge smile on his face, and what I can only assume a rock-hard dick.
The ladies closed the door, turned, and both started laughing uncontrollably. They hugged momentarily, looked into each other’s eyes, and shared their first French kiss. I was turned on as I rubbed my erect manhood through my chinos.
As they separated both looked at me. “This is going to be a fun night,” said Connie. As Crystal put back on her tank Connie followed suit. When Connie reached me, I opened my arms and we hugged and then kissed passionately. “That was nice. I’ve been wanting to kiss you since last week,” she said.
Over the next hour, we all talked as I made a salad, poured wine, and ate pizza. We all shared information about ourselves filling in each other about our background of college, where we grew up, failed relationships, and how we ended up in wine country.
As I cleaned up the dinner dishes Crystal took charge. Standing up from the kitchen island she slowly did a strip tease for Connie. “When I saw you last week, I knew I wanted to hook up with you. You’re such a hot MILF,” she said.
“Oh, my Crystal, I thought the same thing about you too. And Jay. But I was so confused about your relationship with Jay. You two have chemistry,” said Connie. She now slowly removed her clothes, now standing buck naked in my kitchen.
“Well, shit! I guess I better get naked too!” I said. I pulled off my polo shirt and before I could reach for my belt Connie was doing it for me. I think Crystal was a bit jealous as she soon joined in removing my pants and boxers.
“His fantasy is to have us suck his cock and balls at the same time,” Crystal told Connie.
“I think that’s every man’s fantasy,” Connie said laughing.
The two took turns sharing my cock and balls, stroking me, and Crystal even stuck a finger in my ass. At one point Connie deep-throated me and I grabbed her head and thrusted deep into her throat in turbo speed until she gagged several times and slapped me on my ass signaling she needed to breathe.
I asked the ladies if they like to go to the couch or the master suite and both agreed to go to my bedroom. Crystal pulled back the bedding leaving just the bottom fitted sheet and the four pillows on the bed.
It was apparent that both ladies had experienced a threesome before, so I just let them take the lead at this point. Besides, I wanted to watch them for some hot girl-on-girl action.
“Why don’t you ladies enjoy yourselves,” I said. “I’ll watch and slowly stroke my cock.”
Before I knew it they were kissing passionately, their legs and arms intertwined like several pretzels. Connie made the first bold move by going down on Crystal’s shaved pussy. It wasn’t long before Crystal was withering in pleasure, moaning, and squirting all over Connie’s face. I rolled Connie over and kissed her to taste Crystal’s juices.
“Hey, this is our time, Jay,” Crystal teased. “Go sit down Mr. Horny.”
The ladies resumed kissing and Crystal had Connie’s tits in her hands and mouth within minutes. Miss Calderon moved down and was between Connie’s legs licking and sucking her kitty. She’d add a finger or two every now and then, but she was on her knees in the yoga downward dog position.
I stepped up to the bed and began rubbing Crystal’s pussy from behind causing her to moan. As I looked at Connie eye to eye she mouthed the words, “Fuck her.” I simply smiled in reply.
I climbed on the bed, got on my knees, and grabbed Crystal by the hips. I slowly pushed my throbbing cock into her tight pussy. She moaned and thrust her ass back on my cock taking my full length and girth.
“Jay, fuck her silly,” said Connie. She grabbed Crystal’s head and pushed it down into her pussy.
This had been my dream since I was probably thirteen: a threesome with two women. I was fucking one woman while she was eating the pussy of the other. Sure, it’s a common scene in porn, but to live it out in real life was fucking amazing.
Crystal and I were rocking in a good rhythm while I was also enjoying watching the girls. Connie was moaning and playing with both of her tits when she announced she was close to summiting the mountain.
Crystal took that as a clue to suck harder on Connie’s clit while I once again grabbed her hips and just started jackhammering my poor Latina’s honey pot.
“Cum for me Connie!” I yelled. “Let it go! Enjoy yourself! Cum for me baby!”
Simultaneously both Connie and I let out a primal grunt as we reached climax. I blew one good load into Crystal’s pussy and pulled out shooting several pearl-colored ropes of my jizz on her ass and lower back. Connie was still shivering a good eight seconds later when I refocused on her.
Crystal collapsed onto the bed between Connie’s legs. “That was amazing,” said Connie. “Damn Crystal, you really know how to pleasure a woman.”
Laughing, “I had a lot of practice in college,” said Crystal.
This piqued Connie’s interest. “Oh, do tell please.”
Rolling onto her back, Crystal continued, “One night in the dorms a few of us girls were drunk and complaining about not getting any action. One girl said she’d pay to have her pussy eaten while another said she’d do it for free if she’d return the favor. The next thing I knew the four of us were naked and going down on each other. We’d get together about once a month to pleasure each other. Those sessions turned into full-on swapping of partners, kissing, and toys. Hell, Debbie bought a strap-on for us to use on each other.”
I was a bit stunned. But then again this is the same young woman who proposed an FWB relationship to me one short week ago. My perverted brain was imagining four college girls getting each other off in the same little dorm room.
Connie mentioned that she was thirsty, so I offered to go get drinks from the kitchen. “Let me help you, Jay,” said Connie
As I was pouring water for the three of us Connie hugged me from behind and caressed my chest and stomach, then tweaked my nipples. “Mmmm, I love nipple play,” I told Connie.
“So do I. I’m waiting to have some one-on-one time with you,” she said. “When you’re ready I really want you to fuck my brains out. Do you think Crystal will mind?”
“Not at all. She’s very open and she’ll understand,” I replied.
When we returned to the master suite, I handed Crystal her water and took a seat in my club chair in the corner while the girls sat on the bed. We all talked a bit sharing a few of our hottest sexual encounters. I found myself stroking my cock listening to both ladies.
“Looks like someone is ready to go,” Connie joked. After a short pause she continued, “Crystal, would you mind if Jay and I played alone for about fifteen or twenty minutes? I need a good fuck.”
Crystal teased, “Only if I can sit in his chair and watch.” We all broke into laughter.
As I got up from the chair Crystal slid off the bed and moved to my chair. Connie and I started kissing and allowing our hands to caress each other’s bodies. Before I knew it Connie had moved into the sixty-nine position and was taking my cock into her mouth.
As I looked up at her shaved pussy, I admired her large labia and her stimulated clit. But then I noticed her starfish. I leaned up and started aggressively rimming Connie’s ass. This caused her to twitch, and my tongue slid down to her pussy. As I licked her outer lips I could feel her using her tongue to circle my mushroom head. The longer she went the faster she went.
I finally had to ask her to stop, or I’d blow my load, and I wanted to fuck this hot MILF. Connie maneuvered so that she was now laying on her side facing me.
“It sounds like you’ve been in a dry spell. What positions do you like?” I asked.
Connie smiled coyly. “Well, I like them all. I usually just go with the flow. But, in all honesty, I love cowgirl, reverse cowgirl, doggy, and another one I don’t even know the name of,” she said laughing.
“OK, describe it,” I said.
“You’re on your back and I’m riding you in cowgirl. Then I like to put my arms back for support and kick my legs out so they’re next to your torso. I use my legs and hips to raise up and down on your cock. I love watching cock disappear into my pussy. It also gives the guy a great view, and he can easily play with my clit,” she said so matter of fact.
“I love that position too. Crystal, any idea what it’s called?” I asked.
Laughing, “That is a great position, Connie. I think it’s called ‘Rocking Horse.’”
“Fuck, I’m so horny. No foreplay, just fuck me Jay,” Connie said.
“Climb aboard,” I joked. Connie soon lowered her dripping wet pussy onto my rock-hard cock. We started in a nice slow sensual fuck. Soon I was licking and sucking on her tits causing her to moan even more.
After about six minutes Connie told me she was going to spin into reverse cowgirl. After she was in position and rocking on my dick, I began dirty talking to her telling her how sexy her ass was.
“Watching your ass and pussy rock on my cock is so hot Connie. And your browneye is so tempting,” I said. “I want to finger your ass. I want to rim your ass. I want to fuck your ass too.”
“Maybe the next time we can do all of that. Tonight, just fuck my pussy,” Connie said seriously.
“I’ll fuck your pussy all right, but you have all of the control right now,” I said as I gave her a playful slap on her butt.
“You’re right. Let’s change again. I want you to just pound me in doggy,” she said while trying to catch her breath.
“You two look so hot,” Crystal said from the corner chair. I looked over to see her with two fingers deep inside her pussy.
Connie was now on her knees in the center of the bed. I kneeled behind her and admired her ass and pussy. Taking my throbbing manhood in my hand I rubbed my head up and down on her wet slit causing her to moan. I slowly pushed just the head into her tunnel.
“What do you think about a finger in your ass as you’re about to climax?” I asked.
Giggling, “You really do love my ass, don’t you? Yes, that will put me over the edge for sure,” Connie said.
I started in a nice slow motion. I could see Connie’s tits hanging down and swaying in my dresser mirror and she looked hot. We made eye contact in the mirror and gave each other a nice smile.
We had been going at it in doggy about ten minutes when I could feel the walls of her pussy start to spasm. “Cum for me baby!”
“Yes, I’m about to climax!” Connie yelled.
I gathered up all of my saliva in my mouth and dripped it down her ass crack. I took my index finger and lubed her asshole and slowly pressed in two knuckles deep.
“Cum for me! Let it go!” I yelled as I slapped her ass.
“Oh fuck! Oh, fuck! Oh, fuck!” Connie cried. “I’m cumming!” She pushed back on my cock and her body rode out the wave of pleasure as she was breathing heavily.
I was still pummeling her pussy but the sight, sound, and tightness of her pussy caused me to climax as I blasted a load deep into her cunt. Before I could pull out I heard Crystal behind me.
“Connie, can I eat Jay’s cum from your pussy?” she asked.
“Oh, that is so hot. Yes. And share his load with me please,” Connie panted.
Alright, I almost got an instant erection listening to my two ladies talk about eating cum from a pussy and then sharing my nut. I felt Crystal’s hands on my hips slowly pulling me away from Connie’s ass.
Crystal leaned in and awaited my white river of spunk to exit Connie’s pussy, and when it started to trickle out, she licked up every drop over the next twenty seconds.
Connie fell onto the bed and rolled over, Crystal climbed up her torso and straddled her hips, leaned over and slowly dripped some of my cum down into Connie’s awaiting mouth.
“Now that is so fucking hot,” I said.
Connie swallowed and told Crystal to kiss her, and then told me to join in the fun. The girls kissed and swapped my seed as their tongues danced in a ten-second passionate kiss.
Crystal looked at me and said, “Kiss us both and taste your cum you big stud.”
I did as requested. I now had some of my sticky man milk in my own mouth as I kissed both ladies. We all cuddled on the bed silently for about ten minutes before Connie spoke.
“I need to get home. My fifteen-year-old daughter has probably texted me a hundred times,” she said. She noticed my alarm clock on the bedside table, “Fuck, it’s already ten o’clock. Can I take a quick shower?”
“Of course. I’ll get you a fresh towel,” I said.
Fifteen minutes later the three of us all kissed at the front door.
As she opened the door I stopped her, “I need your phone number.”
“You two know where to find me,” Connie said with a smirk as she exited and walked down the walk towards her car. Stopping at the sidewalk, “Come to the winery next Friday.”
Crystal and I smiled at each other, and I closed the door. “Are you ready for a dip in the pool?” I asked.
Raising an eyebrow she replied, “Are you ready for an underwater blowjob?”
The End
