It was 1994. I was just 18 and still in high school at the time on a family vacation down to Florida. We were staying with my “Aunt” Becky and her family at their beach condo. She wasn’t really my aunt, she was my mom’s best friend from childhood and i’d known her my whole life. She practically raised me with my mom. She wasn’t blood, but she was family. She was 36 years old at the time and was an extremely active woman. She ran half marathons and biked and had even been an aerobics instructor in the 80s. She was a fit and attractive woman whose body type had probably done more to inform what I find attractive in a woman. She looked a lot like Lynda Carter, the actress who played Wonder Woman in the 70s. Dark hair, small waist and wide hips, and a huge pair of tits. I’d had a crush on her for as long as I’d been aware of the concept of physical attraction.
My mom married my dad right after high school and I was born 6 months later (you do the math), so I’d grown up with very young parents who didn’t put a lot of restrictions on me as a kid. I was half feral and always getting into some trouble. Vandalism, shop lifting, and fighting were all pretty common problems for me, but nothing occupied my time more than the quest for pussy. From the moment puberty hit I was trying to grope, kiss, finger, and fuck every girl i knew. Church youth group had been a very fruitful time in my young life. I fingered and sucked the tits of a girl at a church lock in and i got my first handjob at camp that summer before. I was a virgin but I wasn’t completely inexperienced. But the quest to finally fuck someone had yet to be accomplished.
I can still vividly remember the moment that set everything in motion. Everyone in the house was getting ready to go down to the beach. My mother was in the living room applying sunscreen to my little brother and “Aunt” Becky’s kids, my dad had set up camp in the downstairs bathroom, my “Uncle” Ted was loading lounge chairs, blankets, and other beach supplies into their van. I needed to change into trunks and I surely didn’t want to do it in the bathroom my dad was currently destroying so I decided to go upstairs to change in the other bathroom.
I probably should have knocked but I didn’t, i think about that all the time, still. What if i had just knocked? Instead I burst open the bathroom door to reveal my “aunt” Becky completely fucking naked applying sunscreen to her breasts. I just froze. Here was this full bodied older woman standing nude in front of me, her hands rubbing lotion over her large breasts, I remember her nipples seemed enormous to me. Her bush was trimmed into a landing strip. Her body was insane to me. I drank it in. It was probably 4 seconds tops before she yelled “Jack, what are you doing? Get out of here!” I was still frozen in horny shock at the site of her nude form, she turned away unintentionally giving me a view of her ass, her big full sexy ass, the one that had turned me into the booty obsessed pervert i am today. She began backing that big ass towards me and once it made contact with my body she used it to push me out of the bathroom and into the hallway before turning around and giving me a very quick view of her nude front before she shut the door in my face. I stood outside that door until she emerged in her very flattering one piece. She glared at me but said nothing and then left to go be with everyone else. I stood there wondering if she was telling my parents what just happened. Was i in trouble? Was Ted gonna kill me? Insane scenarios raced in my mind as i got dressed in my swim trunks and went downstairs. No one said anything. We piled into the minivan and headed for the beach.
Things were weird all afternoon at the beach. I couldn’t keep my eyes off of Becky. Her body looked amazing in that bathing suit. I stared at her as she lay out with my mom, face down with her round cheeks peaking out of her tanga cut swimsuit. I kept getting erections all day and was constantly sticking my hard-on in my waistband trying to hide it from everyone. Whenever Becky caught me looking at her she would just glare at me. She hated me. The horny little pervert who was ogling her who she was stuck with all week. After a few hours we packed up the van. I went straight for the backseat and was shocked when Aunt Becky got back there with me with her youngest daughter. My mom rode in the middle row with my brother and Becky’s older daughter and son. The Dads were up front. It was only a 10 minute drive from the beach to their house, but it felt like an eternity. During the drive Becky brushed her leg up against mine and put a hand on my knee, I looked over at her and she gave me a smile. My mom asked her something and she quickly took her hand off my knee and answered. “that was fucking weird”, I thought.
That night we cooked out and “Aunt” Becky’s attitude towards me seemingly changed back to normal. She was her warm loving self and I felt comfortable and assumed that she’d forgiven me for the incident today. All seemed right in my world, except I still stared at her ass in her tight kaki shorts and her breasts in her lowcut top. She was sex personified to me. I was hypnotized by her. Every time she caught me looking that night she didn’t glare, she’d just smile.
After a long day it was time for bed. My parents slept in the upstairs guest room. The younger kids were all sharing a tent that was setup on the back deck. Aunt Becky and Ted had their room and i was given the pull out couch in the living room. The house was quiet and i hadn’t yet fallen asleep when I heard the foot steps coming down the stairs and into the living room. I turned over and saw Aunt Becky in a short nightgown approaching me. “aunt Becky?” I said. “Shhh” she responded in a whisper.
She sat down on the bed and i sat up, extremely confused. “So we should talk about today, huh?” She said to me. I just shrugged not sure how to respond. “I’m sorry I was mad at you today at the beach. I realize you didn’t walk in on me on purpose. I was just embarrassed and I know you were probably embarrassed too. I just wasn’t thinking and should have locked the bathroom door while I was getting ready. It’s not your fault, it’s mine”, she told me with a comforting tone. “I just wanted you to know that I’m not gonna say anything to your mom about it. There’s no reason for anyone else to know. It wasn’t like you were peeping or anything. I know you’re a good kid and we can just pretend it never happened, right?”
I sat silently and listened to her as she went on for a little bit longer. I was only half paying attention to her words at this point, my eyes had instead been transfixed on her cleavage as her large breasts were threatening to spill out of her nightgown. My cock was getting hard and all i could think about was how big her nipples were. “Jack?” Her saying my name snapped me out of it. “Were you staring at my tits again?” She asked accusingly. I tried to deny it but she knew i was full of shit. She laughed. “I saw you looking at them all day at the beach. I guess it’s not your fault. They’re probably the first real tits you’ve seen besides your mom’s.”
“No” I admitted to her, “I’ve seen a few girl’s boobs”. She replied kinda shocked by my revelation “oh really? How many?” I told her about the two different girls from my church and shared the stories of my church lock-in and summer camp adventures. “You’re just like your mom was. She was always getting into trouble with boys even before she started dating your dad.” I hadn’t ever considered this possibility much but it made sense. “were you like that too?” I asked. “not exactly” she said, “I didn’t have sex until i got to college, but i did other stuff with boys. I was really good at handjobs in highschool” she laughed reminiscing about her youth. “What else?” I almost pleaded for more info. My cock was hard as a rock. She cocked an eyebrow “i don’t know if should be telling you all this”.
I protested and she continued “well I had a reputation for being a tease from some of the guys at our school because I didn’t have sex, but there was a group of guys I was friends with who I regularly gave blowjobs to.” I was in disbelief. “Can you keep a secret?” I promised her I could. “Your dad was one of the guys I used to give head to. Before he started dating your mom.” I couldn’t believe it. “Yeah, me and your dad hooked up a bunch until your mom decided she wanted him. We did pretty much everything but fuck. Your dad has a really big cock, I probably should have never told your mom that. She had to have him for herself” she chuckled, “there’s probably a different universe out there where I would have ended up being your mom instead of her.” I was in absolute heaven hearing these stories about Aunt Becky and my dad. What a lucky motherfucker. I was jealous of him. “So you’ve fingered a girl and gotten a handjob, huh?” I told her yes. She got very serious and looked me right in the eyes making sure I had her full attention “Has anyone sucked your cock before?” I shook my head. “Would you like me to be your first?” she continued. My heart almost exploded in my chest. I couldn’t believe my ears. My whole body felt like it was on fire with desire.
She pulled the straps of her nightgown off her shoulders revealing her large breasts to me again. “Do you want to touch them?” she asked. I instinctively reached up for them, cupping them with both hands, running my fingers underneath and then up over her nipples, taking the left one in-between my fingers and pulling on it. She gasped. “They’re very sensitive. You can suck them if you want.” I didn’t need anymore of an invitation and leaned forward taking her right nipple into my mouth while i pulled on the left again. I went back and forth sucking on each like a nursing baby. She had moved her hand down to my crotch and was squeezing my cock through my pajama bottoms. “Take your pants off” she told me. I did as she said, and slid them down my hips, my cock sprang free. “I guess you take after your dad” she remarked on the size of my member. She began stroking it. I was ready to die happy. Here was a sexy older woman who had known me my entire life stroking my inexperienced teenage cock with her right hand while I sucked on her tits. I had never been hornier in my entire life. A statement that might still be true to this day. She put a hand on my chest and pushed me onto my back and then kissed her way up my thighs before taking my cock into her mouth. Her lips, wet and hot expertly slid their way up and down my shaft. She fondled my balls with one hand and stroked the base of my cock with the other while she began sucking my cock faster. I knew I wouldn’t last long. This was heaven. This was the greatest moment of my teenage life. I was in absolute ecstasy. “Are you about to cum?” she asked me. I nodded that I was. She stopped sucking my cock and slid her nightgown down off of her hips and then climbed on top of me. “Sorry, I am greedy. I want to be your first.” and with that she took her cock and guided it into her wet warm pussy. My once virgin cock sliding into her warm folds as she began to ride me. “Oh fuck. You’re bigger than Ted.” she said to me. Wether it was true or not didn’t matter to my 18 year old ears. All I cared about was that my cock was inside of her and she was loving it. I wish I could have lasted a little bit longer but I was way too excited. I exploded inside her pussy. Filling her up with one the largest loads of my life. She collapsed on top of me. “Did you like that?” she asked. I could barely muster a response. “This is out little secret, okay?” I nodded at her. “If you promise not to tell anyone, not even your little friends, we can do this again some more while you’re here this week.” I swore myself to secrecy.
For the rest of that week, she’d sneak downstairs and give me amazing blowjobs and then fucking me in every position that I wanted to try, always humming inside her. It was the greatest week of my life. She got pregnant around that time and though she’s never acknowledged it to me at any point of my life, I know it her 3rd child was most likely mine. We never had sex again after that week, and after I graduated high school and went off to college I rarely ever saw her. Usually events like my mom’s 40th and 50th birthday or my parents anniversary. I still think about her often though and I have no regrets about that magical week in 1994.
Source: reddit.com/r/Erotica/comments/120u4a5/memories_of_spring_break_1994