This is a story about Megan, a recently turned 18 high school cheerleader. She had dark hair, an athletic figure, about 5’8 and 120 pounds. She was confident in life and always knew exactly what she wanted and knew how to get it. She lived in a coastal town, house right next to the beach.
Recently she had realized that she finds older women quite attractive. Something about feeling intimacy with a mature woman had her quite intrigued. She could see she was crushing heavily on her teachers, friends’ moms, and even her own aunt. But she knows she can’t ruin relationships with her friends and families just for curiosity. The only option she could see was to go on an app which was designed for dating older women. It was her first try at this and wanted to see what’s out there. She was amazed by looking at the number of available older women to date. Some were just looking for a sugar baby, some only wanted to hook up, and some were like her who were just curious and wanted to experience some deep connection.
She posted pics of her in cheerleading outfit, and some when she went for hiking. All it needed was funny bio which she nailed it. In no time, her inbox was flooding with messages. It was a bit overwhelming at first, but she spent the next few hours just looking at the profiles. But then one profile caught her eye. It was a 51 yo woman named Irene who lived in the same town. She couldn’t believe a woman her age could look so sexy. She had a voluptuous figure, 5’7 and 150 lbs. Large breasts and a curvy ass most women would kill for. Megan noticed her ass too and also the tramp stamp above it. She had never been so horny by just looking at someone’s pic.
Irene: Hey Megan, I liked your bio. It’s so funny;)
Megan: Heyy Irene, haha thanks. You look really beautiful in that pic on the beach.
Irene: Thanks. You are quite gorgeous too. So what are you looking for here?
Megan: I wish I knew exactly. But I guess I want to form a connection and see where things go.
Irene: No it’s okay. No one is expected to know what they want. And you’re still 18. I can understand your point and that works for me.
Megan: Thanks for understanding. It has been so hard for me the last few days as I can’t talk about my feelings to anyone. I don’t think anyone can understand.
Irene: Well that’s true. But it’s important to talk it out with someone.
Megan: Maybe we can talk about it more over a few drinks?
Irene: Haha are you even old enough to get a drink at a bar?
Megan: I have a fake ID. It’s all about the confidence to get in haha.
Irene: Wow I hope it works
Megan: It will. So see you tomorrow at the pleasant st pub? Its right near the entrance to the beach.
Irene: It’s a date! pick me up around 7?
(Irene in her many lesbian relationships preferred having to act the more feminine role. She was also a bit old school and gave importance to chivalry of her partners)
Megan: Sure thing beautiful. Where should I pick you up?
Irene: Thanks sweetie. At the bus stop near main st?
Sweetie? This was the first time she gave her a cute little nickname. She was ecstatic.
Megan: great! See you then;)
Megan couldn’t wait for the date. Soon after she returned from school, she started preparing for the evening. She was taking Irene to a pub on the beach and had dressed a little casually hoping to show her figure a bit more.
Megan: On my way!
Irene: Great. I am almost ready.
Megan soon reached the bus stop where she was picking up Irene. When she saw her, she couldn’t believe she could get even more beautiful than the pics she had on her profile. Her jaw dropped looking at a red cropped t-shirt, and a purple side knot knee-length skirt. She truly had an amazing curvy milf figure and could see her stomach and also the tramp stamp from behind. Her hair was grayish blonde and put together in a sexy messy bun. Her cleavage was well defined in her dress. And her ass begged to be squeezed. But she managed to contain her excitement. She got out of her car and hugged her tight. She loved the feel of Irene’s breast pushing against her.
Megan: Hey Irene, it’s really nice to see you. Loved your dress.
Irene: Thanks babe. I am looking forward to this evening. I loved that you picked a spot right on the beach.
Megan: Yeah, I love that spot. They also light bonfires later in the evening.
On the way to the pub, they are just having some small talks and joking around to feel at ease. Irene loved Megan’s sense of humor. Beauty and Witty! They went to the pub and ordered a full bottle of wine and some appetizers. They were having a wonderful time teasing and flirting with each other. After finishing their first glass of wine, Megan poured another one. But she accidentally spilled some on Irene’s t-shirt. She immediately took the paper towel and started to clean her tshirt just above her big breasts.
Megan: Oh god! I’m so sorry. It’s so embarrassing
Irene: It’s okay dear. Since we are at the beach, it’ll be better to just take my tshirt off now and let it dry.
Megan: Okay. Let me do that too.
They both removed their tshirt. Megan was so turned on by the sight of Irene removing her tshirt. She hoped she didn’t have to remove her panty too as it got wetter.
Megan: Wow you look so hot right now!
Irene: Hahaha thanks. You too babe! So you find older women attractive?
Megan: Yes I do
Irene: Why’s that?
Megan: I feel like I can reach a deeper level of connection and intimacy with them. But I don’t know yet. That’s why I am out trying to find the answers.
Irene: Fair enough. But here’s the thing. I know you’re looking for just a connection. But if things go well between us, and we share an emotional and physical bond, I want us to be in a serious relationship at some point.
Megan: Yeah I understand. Thanks for clarifying. So how long have you been on this app?
Irene: A few months now. Hard to find a pretty young girl who wants a relationship with me and not just a hookup and also loves to eat ass!
Megan was shocked at her response. Did she just bring up eating ass on the first date in a candid conversation?
Megan: Woah! You’re quite bold and brutally honest. I like that.
Irene: When you get to be my age, you don’t have much time to waste on casual flings. So I like to be upfront about my needs. Just eating my pussy doesn’t make me cum. I wish it did but it doesn’t.
Megan: Well, I have never eaten ass before.
Irene: It’s not about the experience. But the attitude that matters to me hahaha.
Megan: Right?! I mean looking at your ass, I am surprised you didn’t find many girls who’d devour that in a second.
Irene: Aw you’re just too kind!
They both looked each other in the eyes with a smile and could feel there’s something special going on right. Then their orders arrived, and they enjoyed a delicious dinner. Bonfire also lit up near them and the mood got even more romantic. They didn’t talk. Just admired each other and how lucky they were to be in each other’s presence.
After dinner, Megan asked her to walk with her on the beach. Moon was bright and full. They walked for a while holding hands. Megan then decided to wrap her hand around Irene’s waist. A shiver went down Irene’s spine. She reciprocated by placing her head on Megan’s shoulder. Finally, they stopped walking and faced each other. Looked each other in the eye. Megan leaned in for a kiss. And they kissed each other passionately with tongue fully into each other’s mouth. Megan had been fantasizing about being with a mature lady for such a long time and the kiss just felt too good and right. For a moment, it was just Irene and her in the world. Nothing else mattered. As they are kissing, Megan is massaging Irene’s ass and squishing it harder and harder. Irene’s hands are wrapped around Megan’s neck.
Irene: Wow babe that was so good! You are such an amazing kisser.
Megan: So are you darling! It has been lovely. I enjoyed every second of it.
They made out some more before heading back to the car. On the way back, they continued with their flirting but this time it was more physical sensual touches. Megan had one hand on the steering wheel, while the other one rubbing Irene’s legs. Irene had a silent moan.
They reached Irene’s place. She invited her in for more drinks. They had some more wine sitting at the dining table.
Irene: I really enjoyed this evening. And you are so beautiful and charming.
Megan: So are you. I would like to make out some more.
She gestured for Irene to sit on her lap. Megan was quite strong on account of all the core workouts she did as a cheerleader. She often had to lift other girls as part of her cheerleading exercises routine. Irene was surprised by her gesture but sat on her lap facing her. She slipped her tongue deep inside Megan’s mouth and twirled around with hers. Megan loved that feel. Megan started to caress Irene’s butt with one hand while playing with her hair with other. Soon her hand slipped into Irene’s skirt, and she was playing with her ass just a little bit more intimately. Irene loved that and moaned while their tongues still stuck together. She takes off Irene’s bra and hers too. Megan plays with her 38Ds.
Irene: oh my god I am so turned on right now. Carry me to my bedroom.
Megan carried her kissing on their way to the bedroom. She then drops her in her bed. Takes off her skirt and hers as well. Irene is laid on her back. She plays with her big breasts and submerges her face in between them. Her tits are so hard right now. She gives them a little bite. Megan then remembered about eating her ass and how it’s imperative for her to cum. She rolls her over so Irene’s laying on the stomach. She sees the butterfly tramp stamp, her stunning juicy ass, and doesn’t resist anymore. She slowly takes off her panties and slides them down Irene’s legs. That was the last piece of clothing on her body. Now, all it needs is her tongue playing with Irene’s asshole. She had never done that before. But she let her feelings guide her on what to do. She started kissing her from the top at the neck. Slowly making her way down on the butt cheeks.
After that, she started licking the crack between her ass cheeks. She squished her butt cheeks apart and could see the asshole. Here we go! She rolled her tongue around the outer ring for a while. Irene’s moans were getting louder and louder. And then she went for it. Her tongue was inside her hole. As Irene started to feel that and relax her anal muscles, Megan continued to push her tongue deeper and deeper with each stroke. She would also just keep her tongue inside for a few moments and rotate it inside. Her ass was trembling like never before. To Megan’s delight, she loved doing this. She moaned too as she was pushing her tongue inside. She wanted to play with her ass the moment she saw her in the pics on her profile. And now she has. She couldn’t believe what she was doing. She didn’t care. At that moment, all she could think of was that juicy warm feeling deep inside her ass.
Irene finally couldn’t take it anymore. She squirted and wet the bed. She had never cum so hard. It was like an explosion, and she was on cloud number nine. Megan had a surreal and deep realization that she had made Irene cum by eating her ass just as she had hoped for. She saw the effect it had on Irene and began to lightly kiss her all along her trembling body.
Irene: Oh my god! my baby!! Thank you so much. I can’t believe you have never eaten ass before. That was the best cum of my life.
Megan: I could go all night long sweetheart! I loved eating your ass.
Irene: Wow you’re so natural at this. My body is still trembling from that. Come cuddle me and take care of me. Let’s take a small break while I recover from this euphoria.
Irene rolled to her side, Megan faced her and pulled her closer. She rested Irene’s leg on top of hers, feeling her warm dripping wet pussy with her knee. Irene laid her head on Megan’s arms and Megan fondled with her hair, her arms, her legs, and her breast. While they were recovering, they talked:
Irene: My baby, I’m so happy to have met you. I have never squirted before in my life. I have had my ass eaten before and I have cum, but never squirted.
Megan: Making you squirt like this was the best feeling I have ever had.
They kissed.
Irene: So do you live with your parents?
Megan: Yeah but they are vacationing in Europe for a month. So I have the house to myself. I couldn’t join them as I had school.
Irene: Oh right I forgot you’re still in school.
Megan: Good thing it’s Saturday tomorrow and I don’t have to go.
Irene: Oh yay! So can you stay the night here?
Megan: Yeah I want to wake up next to the most beautiful woman I just met.
Irene: Ofcourse babe. It’d make me really happy if you stay.
They kissed again. This time tongue deep in their mouths. It turned them on.
Irene: Now it’s my time to rock your world.
Irene got on top of Megan with legs on each side of Megan’s. Their pussies touching and Irene started to rub them first slowly and then picked up the pace to Megan’s body. “Oh my god! Yess! Yess!! Right there” shouted Megan. Irene was sweating profusely from going hard but she just kept on going. And then she heard Megan’s scream of joy. It was powerful. Irene smiled at her still going on but now only massaging her pussy with hers. Megan gathered herself and tried to get up to kiss Irene who has been on her lap. She put her hand in Irene’s hair which was now totally wet from her sweat. Her body too. Megan loved that cool sweaty feel from Irene’s body. She started to lick her sweat off. “Oo delicious!”, exclaimed Megan.
Next Irene got off her lap and pushed Megan’s shoulder to the bed. She straddled Megan’s face getting in a 69 position. She started licking her pussy and all the sweet juice flowing out of it. Megan also started licking Irene’s pussy. The feeling was sensational. She finished in no time. This time even bigger cum for Megan who almost squirted. But Irene was not finished yet. Still sitting on her face, she got her back straight. Now Megan had access to her asshole. Megan pushed her tongue deep inside her ass. She liked the cool feeling from her sweat followed by the warmth of her ass. Irene bouncing on her face enjoyed the wet tongue in the ass and Megan’s fingers in her pussy. They continued pleasuring each other for another hour before none of them could take anymore.
Megan: Wow! I’m speechless!
Irene: I have never said this to anyone after first-time sex. But you deserve it. I’m obsessed with you! I love you and I can’t see myself with anyone but you.
Megan: Aww thank you. I love you too my sweet sexy darling.
They kissed.
Irene: Let’s take a shower now. I’ll change the sheets. And cuddle our way to sleep.
Megan: Yes that sounds good.
Megan never thought she’d be so into a woman who is much older than her. She understood it was something that she’d just have to let go of and be in the present and enjoy the time together. And that’s exactly what she was doing. If this night taught her anything, with Irene in her arms, it was to live in the moment. Beautiful things can happen.
The next morning Megan woke up late as usual. She couldn’t find Irene next to her but could hear someone in the kitchen. She freshens up and went to the kitchen and saw Irene making breakfast. She went behind her, put her arms around her stomach, and kissed her neck. “Good morning love”, Megan said. Irene turned her head with a big smile and kissed her lips.
This was the beginning of the rest of their time together. Megan lived in Irene’s place until her parents returned from the Euro trip. She and Irene would make love every night, every day. They were inseparable. They would go to concerts together or just stay in watch movies cuddling each other. It was Megan’s first love and Irene had never been so much in love with someone.
What happens next after Megan’s parents are back will be in the next chapter.