I. MAY 14 – HOME FOR THE SUMMER
I drove the ninety minutes from campus to my mom’s house immediately following my last final of the semester. My freshman year had concluded and I was ready for some time off. A relaxing summer back home after a hectic regimen of classes sounded like just what the doctor ordered. My mom was thrilled when I walked in the door, hugging me tightly before she helped me bring my things inside and up to my bedroom.
“Oh, Nate, you’ll never believe this!” she started once I was unpacked. “My friend Cyndi next door? She’s pregnant. At 46 years old.” My brow furrowed in confusion. “Is that even supposed to be possible?” Mom shook her head. “Not really; very, very rarely. They generally say women are good and finished procreationally at 45. I don’t think she’s breaking any records or anything, but it is very unusual. And a big surprise, of course.” I nodded, my eyes wide as I considered the odd situation. “Is she still single?” Mom nodded with a mischievous smile. “She sure is. Quite the scandal!”
It was a real surprise, but honestly a pretty pleasant one for me. I had a thing for pregnant women and was excited to spend my summer in close proximity to Cyndi’s expanding body. “How far along is she?” I asked, attempting nonchalance. “About 5 months, I think, so she’s showing quite a bit already. Just try not to make a big deal out of it when you see her: she’s feeling pretty embarrassed as it is.”
She was already 5 months into her pregnancy: fantastic! Quickly doing the math, I realized I’d be around until she was 8 1/2 months in. God bless excessively long college breaks! This could be a more interesting 3 1/2 months than I’d anticipated…
Later that afternoon I glimpsed Cyndi returning home from the grocery store. She was wearing a modest, rather loose maternity top, but her belly was unmissable on her slender frame. I didn’t miss a beat, heading straight outside to lend a hand. “Nate!” she exclaimed as I approached. She hugged me, her bump pushing into me pretty darned arousingly. “How are you? You can probably see how I’m doing…” She glanced and motioned down to her cute baby bump. “Yeah, my mom told me. Congratulations! Let me bring these bags inside for you.”
She graciously accepted the help; I grabbed two bags in each hand and she led me inside. Everything was in the house after three trips in and out. Cyndi offered me a bottle of water and asked how school was going. Throughout our light conversation I struggled in vain to keep my eyes off her bump. They just kept returning to its sexy plumpness as if magnetically attracted. I noticed her noticing my stares three times in five minutes. She smiled each time.
II. JUNE 10 – THE SQUIRREL AND THE LOTION
The phone rang one morning when I was alone in the house; it was Cyndi, and she needed my help. A squirrel had fallen into her pool overnight, and she was too grossed out to take care of it on her own. I was on it in a flash, arriving at her pool two minutes after I’d hung up the phone. She was in a bikini, waiting for the squirrel’s corpse to be removed before she could take her morning dip.
Her bare bump was a sight to behold. It had a few more blemishes on it than your average, younger preggo’s belly, but they created a series of pleasantly interesting constellations across her abdomen. There were no hints of stretch marks from her pregnancies 20-something years ago, and there were no new marks from this current gestation, either. Her 6 month belly was roundly shaped and hanging rather low, a faint linea nigra adding some nice character to the whole thing.
Anyway, I had the squirrel to dispose of. I grabbed the long-handled net and scooped it out, tossing it like a lacrosse ball over her fence and into municipal property. She clapped and cheered, her breasts bouncing up and down slightly with the movement. “Thank you, thank you, thank you. You’re a life-saver, Nate. I got so grossed out, I feel like a total wimp. Do you want to go for a dip with me?” I declined as I didn’t have a bathing suit on me. “Well, your house is about 7 feet away,” she replied. “Or, you’re probably wearing underwear, right? No need to be shy!” I smiled and removed my shirt, shoes, socks, and shorts.
“Oh, help me out before we go in, if you don’t mind. I can’t get the sunscreen on so easily anymore. Could you just rub some on my back and my belly for me?” The back I completely understood limited reach-wise, but the belly didn’t make a ton of sense. I’d seen her rub the entirety of her bare bump just in the past 5 minutes or so: she could absolutely apply lotion to herself around that area. I remembered her pleased look when she’d caught me checking the bump out a few weeks ago, and thought it was just a slight possibility that this was a bit of a tease, maybe even a provocation. “Sure,” I replied. She handed me the bottle of sunscreen and I went to work on her back first, finishing the job in a minute or two.
Now with the belly, I really took my time applying the lotion. I rubbed it in until all the white had disappeared, then further until her skin wasn’t at all shiny anymore. Not quitting until it was fully absorbed let me spend significantly more time with my hands on her gorgeous bump. I focused on one little area at a time, working with both hands in small concentric circles. Every square inch finally covered, I pretty much had to call it done after 6 or 7 minutes. She was smiling widely as I finished, similarly to the last time she’d caught me blatantly enjoying her midsection. “Thanks,” she said simply, then turned around and took the stairs down into the pool.
I followed, standing close to her in the shallow end. She had both hands on her bump under the water and her large breasts floated right on the surface of the water. “Did your mom tell you how I got into my delicate condition?” she asked. I shook my head at the forward, unembarrassed question, eager to have her explain it to me. “Well it was a total surprise, obviously. I mean, who the hell gets pregnant at 46? The last time I had a baby I was 24, for God’s sake. My doctor was shocked: basically no one gets knocked up after their very early 40s. I’m a real outlier, turns out.
“The father is this super boring guy I met on Plenty of Fish and only went on the one date with. I didn’t like him that much, but a woman has needs, you know? He has no idea about the pregnancy, by the way, and I don’t intend to ever tell him. He seemed like kind of a loser who probably didn’t have much sex, and I felt bad about myself in a self-destructive way. Thus, unprotected sex seemed perfectly reasonable to me at the moment. The word “condom” never even came up. I’ve been tested since I got pregnant, by the way, and he only gave me the potent sperm, no STDs, luckily.
“It’s just so, so weird, Nate. My other kids are older than you, one of them is already married, and I’m going to have a newborn in a few months. I’ve worked up to the point that I’m pretty excited about the baby, but nervous about the exhaustion and all at my advanced age, of course. The whole situation is just nuts…”
Cyndi stopped her story and blushed. “Sorry, I’m sure I’m oversharing…” I shook my head vigorously. “No, no…I really appreciate that you trust me enough to share all that. I’m here for you, Cyndi…for summer break, at the very least. We could both use a friend right now, I think. I’m an adult, not your girlfriend’s little kid anymore. Please, feel free to share absolutely anything you want with me. I’m honored.” She smiled and touched my arm. “Thank you, Nate. You’re a very good friend.”
We stayed in the pool for another 20 minutes or so, largely quietly. I made sure to stay in until she was ready to get out so that I could get a nice view of her dripping-wet bump. It was very much worth it. She met my stare with a smile once again…
III. JUNE 20 – WINDOWS
Cyndi had raved to my mom about my helping her with groceries, removing the dead squirrel from her pool, and being a patient listener. My mom was thrilled that I’d been so kind to her friend and that we’d become such good friends as well. I thought it was great, too, and was very happy to be a good friend to the mature preggo next dor. Best not to let my mother know how much I wanted to fuck our mutual friend, though.
My and Cyndi’s bedrooms were directly across from each other, maybe 15 yards apart. It was 10 o’clock at night and we were both in our bedrooms. I turned my lights off so as to see into her room more easily: she looked over right when I did so, making me think she at least had an inkling that I may have been watching her. Her clothes were completely removed in short order, inkling of a spy’s presence or not. Even a mere 10 days since I’d last viewed that last bump, its growth was evident, roundness more pronounced. Her breasts were more pendulous, a bit saggier than those of women closer to my age. They hung all the way down and rested on her low-hanging (but far from fully dropped) bump. Her nipples and wide areolas were a dark brown to match her hair. I was very, very hard.
Generally, her skin just looked a bit looser with her extra years, tiny folds appearing even in the areas of her body with very little fat. It was very attractive to me, an extra type of curves added to the already extra-curvy pregnant form in a way I’d never encountered before. The oldest preggo I’d ever seen had a lot to offer; that much was certain. She rubbed her entire body with cocoa butter, liberally and thoroughly. I could see right there how she’d so impressively avoided stretch marks this time around.
Sitting down on the foot of her bed, still fully nude and fully in view, she leaned back a bit and started rubbing her pussy. Her pubic hair was seriously and sexily unkempt, curly and near-black. She rubbed and rubbed all over her clit, labia, and vulva, staring at the middle of my window all the while. While she couldn’t have been able to see me in my pitch-black room, her estimate of where I was probably watching from was quite accurate.
Though she didn’t know it for sure, she maintained this sort of eye contact with me for at least half of her masturbation. When she came, she came loudly, her open window carrying the sound directly through mine. I’d been stroking myself throughout all this, of course, and could no longer hold off my own orgasm once I heard hers. I came pretty loudly, too, excited by the thought that we might be communicating via orgasmic vocalizations. Progress was being made, it felt like.
She had me over the next morning to remove a bunch of boxes from her basement. This was her opportunity to turn her gaze on me after mine had been on her just a few hours ago. I was rather bookish in temperament and general vibe, but I was fit, showing off my modest six-pack when I removed my shirt early in the cleaning process.
IV. JULY 11 – JACUZZI
I watched Cyndi pull into her driveway, grocery bags visible in the back of her car. I rushed out to meet and help her. She was grateful, as usual, and told me she was headed to her jacuzzi to relax after her exhausting shopping trip. Would I like to join her? Absolutely fucking right I would.
She donned her bikini again, and it was noticeably tighter than it had been a month or so ago, struggling to contain both tits and ass. At 7 months along now, I’d say she was just starting to warrant the term “gravid;” I was pathetically smitten. We got into the jacuzzi, jets roaring. Shouting over the sound, Cyndi asked if I’d mind if she removed her top: her heavy breasts were not meant to be contained at this point in her pregnancy. I whole-heartedly gave my blessing, and she unclasped the back of the bikini top, her breasts dropping with a heavy splash into the water as soon as the garment was removed.
“Sorry, Nate,” she said entirely unnecessarily, “I’ve just been so sore since my milk came in last week. My boobs are so swollen and heavy; it’s hell on my back.” I was staring at her nipples, half-visible at the undulating surface of the jacuzzi’s water. She smiled, which seemed to be her default reaction to all my perverted gawking. “The more uncomfortable our breasts get, the more men seem to like them. Is our discomfort the attractive part? I haven’t gotten so many stares in 10 years, minimum.”
I felt my face redden, but couldn’t turn down an active part in this conversation. “No, it’s not the discomfort, at least not for me. They’re big and heavy, and the nipples are huge and dark. That’s what I like to see anyway.” She smiled and put her hands under the water, her body wriggling back and forth for a few moments. Her right hand reemerged with her bikini bottoms in hand.
“I’m gonna need a bit of help, Nate.” Standing up, she repositioned herself on the edge of the jacuzzi, completely nude and legs spread to expose her engorged pussy. “Come on, sweetie, it’s time.” This would be my first contact with female genitalia, and my cock was hard to the point of throbbing as I approached. I rubbed her pussy all over for a minute, making sure to locate the vaginal canal and clitoris just to make certain I had the lay of the land. She didn’t have much patience for my exploring with my hands, as she grabbed the back of my head and shoved my face right into her crotch.
I managed to get her clit in my mouth, sucking, licking, and gently biting until she came loudly. She breathed hard for a few moments, then regained her voice. “Okay, get up here. Lose the underwear.” I stood as I pulled my boxers off and tossed them over the side of the jacuzzi, sitting on the edge as Cyndi got back into the water. My cock was sticking straight up, and she was quickly in position with her head just over it, taking me in her mouth and bobbing up and down rapidly. It was my first blowjob, and it was earth-shattering. I shot in her mouth within about 30 seconds. She swallowed and laughed. “I thought it might be your first time. Not so subtle, buddy.” She smiled at me and I felt no embarrassment.
We were now having a bit of an affair in earnest, it would seem.
V. July 23-25 – Business Trip
Cyndi rang our doorbell at 7 in the morning; my mother and I both rushed to answer. She told us her assistant had fallen ill, and she needed a last minute replacement for the business trip she was taking for the next 3 days. I packed rapidly and went to her car with her, throwing my suitcase in the back. Once our doors were closed, Cyndi let me know there was no business trip, just a luxury hotel room in the country awaiting our lust. My hands didn’t leave her huge, tight 7 1/2 month bared bump once during the 2-hour drive. I was in heaven.
“Strip” she commanded the instant we opened our hotel room door. She pushed me, naked, onto my back on the bed. She tore off her maternity dress; there was nothing underneath but a glorious maternal figure. Kneeling next to me, she blew me for a minute to get me nice and hard. Removing her mouth from my cock, she popped the question: “You’re a virgin, right?” I nodded, red-faced. She mounted me immediately, and my virginity was gone in a poof.
Her pussy enveloping my dick felt phenomenal, unsurprisingly. She rode me cowgirl, so I was able to keep my hands rotating between belly and tits. Bouncing hard and fast, she elicited my first penis-in-vagina orgasm in under a minute. She continued bouncing, cum dripping back down out of her and pooling around my pubic hair, until she got herself off, too. Then she took a nap for a few hours before dinner.
I surrendered to her superior, spectacularly well-practiced fucking skills and was hers to use for the next 2 days. It may have been unusual that she got knocked up at her age, but if it was going to happen to anyone it was going to be someone who’d so clearly maintained her sexual prowess and stamina. Cowgirl, reverse cowgirl, bump-adjusted missionary, doggy, 69, anal…rinse and repeat: my only breaks were my refractory periods and the occasional meal. Her favorite thing seemed to be having me cum directly onto her inflated belly, then having one or both of us thoroughly rub it in until she was shining with my homemade moisturizer. This quickly became my favorite thing, too.
What a thorough and accelerated education Cyndi had provided me! I slept for 17 hours straight when I got home.
VI. August – Bliss is Fleeting
August was the final month of Cyndi’s pregnancy and my summer break. My sexual skills steadily improved with a great deal of practice, to Cyndi’s multi-orgasmic delight. Her last month of pregnancy presented numerous physical obstacles to sex, but we were creative enough to get around most of them. Lots of oral sex resulted.
If I could have stayed with Cyndi and Cyndi could have stayed heavily pregnant, I would have continued on with her indefinitely. But things just don’t work that way.