Stories 18+ My first actual sexual experience with Aunt Maggie

Stories 18+ My first actual sexual experience with Aunt Maggie
My Aunt Margaret, Maggie, was the first adult who treated me like an adult. That has a powerful effect on someone coming of age. It almost never happens with a relative because they usually have known you since childhood and have difficulty separating old memories from the current you. Maybe the reason it worked was because she hadn't seen me in over 10 years and maybe also because there was only 20 years difference in our ages. Maggie lived in New York City and I in Houston, Texas. But I went to college in Boston, well Cambridge to be exact, MIT. 

My first trip to see her was a long weekend in the first semester of my freshman year. Maggie was a heavy set woman with a smile that matched her zest for life. Her long time roommate, Mary, was also a little on the plush side but with an open, friendly smile as well. As a young man I noticed those appearance characteristics a lot. We spent the evening drinking, laughing and telling stories that helped us all get better acquainted. We talked politics; Maggie was passionate about the subject. She told me about the trials of getting ahead when she first moved to New York, as well as the special difficulties of a woman breaking into the technical "man's work" behind the telephone operators. There were stories of men they had dated, some funny, some just under the heading of "an interesting character". There wasn't any animosity toward men in their stories. I did note that there was only one bed room in her Upper East Side apartment, which they obviously shared. I was to sleep on a sofa bed in a small sitting room. It was great, I was in the heart of the greatest city in the world and at the time I even thought I might want to live in New York after graduation. 

Those first two years of visits we never discussed lesbianism directly, and I gathered from other conversations with them both that they might well have been uncomfortable describing themselves that way. The best description would be to say they were basically straight women, who never found a guy they cared as much about or could commit to as much as each other. That caring found expression in some sexual activity some would call lesbian.

My junior year they gave up the Manhattan apartment and moved to Long Island. I was still in love with Manhattan and hated to give up the city on my visits, but I was going there to see Maggie and Mary because wherever they were that was where the good times were. They bought a nice house that even had a guest bedroom and a boat to cruise around the Sound. 

At the house in a small village on Long Island things seemed freer, more comfortable and relaxed. Perhaps it was the lack of neighbors through the next wall, or maybe it was just that we knew each other better. One particular weekend near the end of junior year changed the nature of our friendship. A close friend of theirs had died recently and Mary was away on a business trip when I visited. Maggie and I were alone at the house and she was very depressed thinking of her friend. While hugging her to provide comfort the mood suddenly changed. A kiss was exchanged and that kiss became a full mouth kiss.

"Hey?" she said, as she pulled back just enough for our eyes to meet. "Is there something else here?"

"Not if you don't want there to be," I said, still unsure and not wanting to offend.

"Then let's go," she said and took my arm and led me quickly to the bedroom. We undressed just as fast, perhaps before either of us could think it through and change our minds. I was still a virgin, and anxious for my first experience, though extremely well read on the topic, and experienced in all but penetration.

Unlike some big women, her tits were more normal size. Her plumpish pussy had thin but dark hair that grew in straight lines, almost as if groomed that way. Although I had never had my cock inside a woman, I had eaten some pussy and loved it. I was sure that my skills in cunnilingus could overcome any potential embarrassing lack of experience in actual intercourse; and if not my skills, at least my enthusiasm. As I spread her big thighs to get at her honey pot, she realized what I was about to do.

"No, I don't enjoy that," she said matter-of-factly. I was stunned; it never occurred to me that there was any woman who wouldn't want that sort of attention. It seemed all the more difficult to imagine that it wouldn't be one of the main options for girl on girl sex. From my masturbatorial experience I was worried about stamina, and had really hoped to get her close to climax before entering her. I was hard, and obviously excited about having my first full-fledged sex, all of which I felt certain would work against lasting a long time.

"Are you using something or should I be...?" I awkwardly asked trying to raise the birth control question.

"I haven't had a need to use anything in years," she smiled, "and unless you brought something, we don't have anything to use. Besides, I always wanted a child." She studied my face for a moment. "It'll be fine, it's OK. If you're worried you can pull out and go on my tummy."

My worry didn't diminish much because I had read that pregnancy could result from small emissions prior to ejaculation. I resolved to pull out the moment I thought I might go over the edge. Besides, this must not be her most fertile time of the month or she wouldn't agree, I thought, though I knew my reasoning abilities were rapidly eroding under the demands for blood below my waist.

She guided my stiff cock into her already wet pussy. She was tight and I wondered just how long it had been since a dick was where mine was now. We kissed again and it felt a little less strange this time. Her full soft belly completely touching mine, she was meeting my thrusts with her own. Despite the stimulation from her tight love tunnel I was finding it easy to not rush over the edge. Perhaps it was the unreality of the situation, or that she didn't have porn star looks; whatever the reason I was pumping away and having no trouble enjoying the tingle up and down my cock while not being on the verge of cumming. Maggie, on the other hand was rapidly moving to a massive climax.

"OH!...OH GOD!" she kept saying between moans that came from deep inside her. The pace of her exclamations increased and suddenly she was hugging me tight with her arms while her heavy legs locked around my ass and squeezed me deep into her.

"UUNNNNNNGGGHHHH!" she cried and shuddered all over, her soft curves jiggling and undulating over tense muscles underneath. 

"No man has ever made me cum like that!" she said. 

I was feeling pretty good about myself; first time at bat and I made a woman cum like that and still hadn't shot my load! She soon realized I hadn't finished and without hesitation rolled over on her stomach, then raised her ass by kneeling.

"Do you want to go in my ass?" she asked casually.

"OK" was all I could think of to say.

She spread her copious natural lube around her anus and on my cock. Despite it being much tighter than her pussy I slipped in easily. After a few strokes I could feel myself building toward a climax.

"Do you like it back there?" she asked.

"Yeah, I do, it's good. And we don't have to worry about getting you pregnant."

The extra stimulation and the release of worrying about pregnancy pushed me over the edge and I came in her tight asshole while holding on to those broad cheeks. Not long after cumming my cock deflated and plopped out of her ass.

We cleaned up and dressed to go out for dinner. I was feeling a little awkward about the whole affair. Not regretting it so much as just wondering what we do now, what we talk about. The conversation stalled right after discussing the menu choices. I couldn't stand the silence and had to say something. I started to tell her that was my actual first time, but thankfully realized that would only make things more awkward.

"Did you mean what you said earlier?" I asked in a fashion I hoped was casual but also clearly referenced our intimate time.

"Yes, I did," she paused, "I've always wanted a child, but the usual situation just hasn't come along, and I realize that if it doesn't happen soon that chance will be gone." She stopped because my stunned silence must have made her realize I was processing her remark as a request. "Look, I'm not specifically asking you to give me one if you don't want to. I just want you to know that I would never ask anything of you with regard to the child, and that you don't need to worry about it; it happens or it doesn't."

"OK," I managed to say.

"Did that answer all of your questions?"

"Actually I was asking about the other thing you said...about" lowering my voice, "cumming."

Now she was momentarily caught off guard. Then she reached across the table, took my hand and looked me straight in the eyes.

"Yes, I did. I absolutely did!"

I have to admit, that made me feel pretty good. Later I would wonder how the 'best orgasm from a man' compared with orgasms from women. I would never ask, perhaps because in the back of my mind the qualifier she used gave me the answer.

The next day Maggie and I picked Mary up at the airport when she returned from her business trip. The ride back to the house was filled with talk about Mary's trip and the friends in common she looked in on while away. As soon as we got back to the house Maggie suggested I make myself a drink while they went off to their bedroom to change and for some "girl talk". I didn't have to imagine what it was about, but I just hoped that it wouldn't cause trouble.

I went to the kitchen to make myself a Manhattan. I poured the whiskey, found only white vermouth, decided it didn't matter, and used it. A dash of bitters and a maraschino cherry and I was ready to wait for the ladies. I didn't hear their voices, which at least meant no angry shouting. Then I realized I didn't know and hadn't asked what their agreements and commitments were to each other.

Maggie and Mary emerged in jeans and loose fitting tops. They were both smiling, and Mary seemed to be giving me a closer, and more approving, look than I ever remembered her doing before.

"What do you say to taking the boat out this afternoon?" Mary said, looking at me. "We could do a little swimming too."

"Sounds great, but I don't have a swim suit," I answered.

"We know a place where that doesn't matter," she said with a twinkle in her eyes. "If you're embarrassed you can stay under water."

Then I blushed a little. Then everyone laughed.

"Is there, like a nude beach or something?" I asked.

"No, but there are lots of small islands in the Sound, some not even a hundred feet across, filled with trees and brush and nothing else. They don't even call them islands, but 'rocks', mostly. We know a few where we can get out to swim."

I changed into my jeans and we were soon aboard their boat, The Getaway. There was a small cabin in the bow, just big enough to change clothes if you were limber, but primarily storage for booze, towels and suntan oil. There was an awning to put shade over the back of the boat where six people could sit on the gunnels. Two more comfortable looking folding chairs were strapped to the sides.

We were heading north into Long Island Sound from the little marina with Maggie at the helm. She made a long looping turn to the west and just ahead was one of those small islands. It looked like a small forest of trees sprouting right out of the water. Maggie slowed the engines and we drifted close to it. We were about a mile from the shore, and still 50 feet or so from the island when the engines were cut off and the anchor tossed overboard. Mary got out a battery powered air pump and inflated a gray lifeboat.

"It's very rocky just under the surface close to the island, so we go ashore in this instead of damaging the boat," Mary explained. 

"OK I guess it's 'show time'," Maggie said with a grin. At first I was confused about what she meant. Mary looked at me, then at Maggie. "Alright, I'll start," Maggie continued, "You've both seen me already."

No one tried to turn it into a striptease, at that point it was almost a race to make sure we kept up with Maggie so we would all be naked at the same time. When we were naked Mary looked me over with fairly obvious attention on my cock. I was a little nervous, I'm a 'grower' not a 'shower' and so was only about 3 inches at the time.

"I'll bet that gets a lot bigger under the right conditions," Mary said approvingly.

"Yes," was all I could say in my embarrassment. Then trying to salvage the moment, I added, "I'm sure the right conditions will come along."

"Pretty confident, are we?" She smiled, toying with me.

"Well, let's just say very hopeful," as I gave her an obvious look of pleased appraisal. Her tummy was a little smaller than Maggie's, her breasts about the same size. Her eyes and her smile had the same zest for life in them and I honestly found myself wanting her too. My remark hit exactly the right tone and she smiled and nodded back at me.

In the little boat we paddled the short distance to the island and pulled it part way up the grass and dirt to hold it in place. It felt odd and liberating to be casually nude out in the open. I was also a little afraid we'd be caught, even though there was no way anyone could see us, and we'd see them coming long before they could tell we weren't in swim suits. I guess my apprehension showed.

"Don't worry, no one has ever come by while we're out here," Maggie said reassuringly.

"Yes, a pity too," Mary said mischievously, with her sly and sexy sense of humor.

Maggie opened a small basket and handed out ham sandwiches. From the bottom of the basket a bottle of vodka emerged along with three plastic juice glasses. Very quickly our interactions returned to normal, and for all intents and purposes we could have been on their back porch fully clothed. While on the one hand I was relieved that I didn't have to navigate awkward talk about our nudity and sex, on the other I was curious as to what this meant. Should I really expect sex with Mary? Alone? Or in a three way? My head just reeled trying to figure it out. Then it was as if they could read my mind. Mary reached over and touched my hand. I looked over at her, and she smiled.

"Bob, I know it's hard for you guys to know what to do with women. Sometimes it's nice to just be there with us, nothing sexual happening, even like this," she indicated our state of undress. "Then there are times when we want you to let us know you want us that way, to be just a little bit assertive, but still ready to accept a 'no' if that's how we feel."

"It is hard, Mary. I just don't know what to do or say." Our words related to both the immediate and the general case. Maggie joined in.

"There's a balance a guy has to strike between the two. Obviously there are personality variations, but here's basically what works." 

My attention was highly focused. I realized that I may never get as clear an instruction from women ever again in my life.

"When you're with her, especially when she's talking, give her your complete and undivided attention."

"Listen carefully," Mary interjected, "she may not want you to solve her problem, just commiserate with her. Don't jump in with a solution unless she's asked or you ask if that's what she's looking for."

"If you treat her like that, if there's an interest on her part, she'll give you the 'go ahead' signal," Maggie said with a smile.

"That's just it, Aunt Maggie," I said almost plaintively, "what is the 'go ahead' signal? I seem to miss it, or imagine I've gotten it when I haven't." I was thinking of many unpleasant high school dates, and the frustration and mortification all came back in an instant.

"Don't let those high school experiences ruin you for life," she said reassuringly. "Chances are those girls were confused and going back and forth in their own minds. A real woman, an adult woman will be different."

"If you think you have the signal," Mary added, "make the next move and pause. That's the balance, make the pause because you respect her decision, not because you are unsure or timid."

"The 'next move'?" I was stumped again.

"Don't rush to 'home plate', take each base in turn," Maggie jumped in. "You know about first base, second base etc.?" I nodded, everyone knew that.

"Well think of each remark or action that leads to the idea of sex as a base. Like when we were undressing," Mary clarified.

We did a little swimming and then let the sound of the waves against the little shore be the only sound for a while when Maggie suggested we get back home. Once aboard The Getaway we dressed and again appeared like a normal little outing of friends. On the way back to the house Maggie stopped by the market and picked up fresh oysters.

"You're gonna need 'em," she said to me.

I knew the reputation of oysters and immediately understood her meaning. Maggie was refreshingly without guile or subtlety. After dining on fried oysters and corn on the cob we cleared the table and kitchen. While we were all standing in the combination living room/dining room Maggie sort of took charge and announced that we should all move to the bedroom and "pick up where we left off on the island."

"Do you have the common male fantasy of wanting to see two women together?" Mary asked. I nodded. "Then today is your lucky day." I watched as they suckled each other's tits and fingered each other's pussies. I stroked myself hard and could see the tenderness and love between them. It didn't matter what label anyone put on it. 

For a few minutes I just watched and stroked myself to full hardness. I was trying to imagine what this would be like, what Mary would be like, what I would be allowed to do, and then I remembered their advice to just take this one base at a time. Then Maggie looked over at me as if for the first time since we got to the bedroom.

"Come join us before you make a mess on the floor," she said almost laughing.

I climbed onto the bed and was going to start kissing Maggie, but Mary grabbed me and kissed me hard on the mouth while her hands found my cock and stroked it. Her actions weren't smooth and practiced but they were effective.

"I bet I know what you like," Maggie said then took my cock in her mouth. It felt good but she was only using her lips, there was no tongue action included. I had the feeling she was only doing it because she felt she should since men expected it. At this time I wasn't about to turn her attentions away. We jockeyed for positions on the bed.

I moved to put my head between Mary's legs and she raised her leg in acceptance. Apparently she didn't have a problem getting oral service. Her bush was thin like Maggie's and her inner lips hidden by plump outer lips that begged for fingers to spread them open revealing the goodies inside. I inhaled her hot, musky scent and felt my cock harden a little more. I tried to work my tongue into her tight hole in between flicking and licking her clitoris which thank goodness was large and easy to find. I could feel Mary tensing and making little sounds when I ramped up my action on her clit.

Meanwhile, Mary was working fingers into Maggie's pussy while kissing her inner thighs. Maggie was still dutifully giving me a blow job but it wasn't advancing me closer to orgasm so when she paused to tell me not to cum in her mouth it was easy to answer 'uh-huh'. Things went on like this for a while with my face getting wetter and wetter with Mary's juices. Suddenly Mary tensed up all over and her legs started shaking.

"OH GOD! OH YES! YES! Just like that!!" She cried out. "AHHHHHHH."

Her orgasm triggered Maggie who abandoned my dick to make similar exclamations. It's a good thing I wasn't in Maggie's mouth because their climax put me a lot closer to the edge. I kept suckling on Mary's pussy until she patted my head to indicate I should stop since she couldn't stand any more for the moment. We lay there in a heap then Maggie was the first to notice.

"Look who didn't cum!" she announced.

"We'll have to do something about that," Mary said sexily. We shifted positions a little and Mary took my cock in her mouth. "Just to keep you simmering until I can take you in me," she said.

"And you don't have to worry about babies with her," Maggie chimed in, "she's had the factory removed. Fibroid tumors."

Frankly that did make me feel better. I was raised with a strong sense of responsibility. I didn't want the responsibility for a child, and was determined to avoid it until I felt ready, but if something had happened I knew I'd have to step up in some way. While Mary's pussy was recovering enough to take some cock, I kissed Maggie and fondled her tits. Mary gave better head than Maggie, using her tongue as well as her hands. She knew how to hold a pair of balls, and to squeeze the base of the cock to add to the sensations. Mary hadn't said anything about not cumming in her mouth, but I wanted to be in her pussy when I shot and she was getting me a lot closer to popping off. Mary must have been very experienced with men at one time because she picked up on my impending situation and stopped her stimulation and applied pressure just behind my balls. It didn't hurt as much as it was just uncomfortable, but instantly I was backed away from the edge of cumming, but still hard and horny. She smiled and then resumed sucking me to ever increasing levels of arousal. Maggie was tickling my balls and soon Mary had to use another precisely placed pressure point.

"Why don't you enter me now, Bob," she said softly.

She laid back and spread her legs for me. I slipped between those meaty thighs and let the head of my aching cock find her slippery hole. As I slid into her, Maggie continued to fondle my nuts and that spot just behind them that always gets me. Mary was wet and very tight. Like with Maggie I wondered when she last had a cock in her pussy. Then a new kind of thought entered my head. I wondered if he, or the last man with Maggie, appreciated what remarkable women they had been with or were they just after the feeling on the head of their dicks. 

In order to have our heads closer together I was "riding high" to give me a little more reach over her belly. It was the same position I used with Maggie. The angle put my cock rubbing the head of her clit on each thrust in both directions. Soon Mary was making the sounds I recognized as her impending orgasm. She clutched my back and her nails raked long streaks down me. My excitement rose to a peak and there was a long guttural sound, that I realized was coming from me just as I felt my cum spurting into her tight hole. When our breathing returned to normal I slipped out of her and collapsed on my back. My cock was deflating soaked with our combined juices.

"Maggie, you were right! He's incredible!" Mary said.

"You're both pretty incredible yourselves," I chimed in.

Mary bent over and kissed my cock, in a sort of 'thank you' that turned into licking our juices off it. In truth, it was probably mostly her juices that coated my cock, since I had stayed in her till I quit cumming. I had never heard of "cream pie eating" and probably would have thought it gross under ordinary circumstances, but I was still caught up in the excitement and too embarrassed not to return the favor. I worked my head between her legs and began to lick her out. 

"Oh my God!" Maggie exclaimed. "I've never seen a man do that!"

"Me either!" Mary added. "What's beyond 'incredible'?" she asked rhetorically.

"I have no idea," Maggie said. How could I stop now.

In addition to the sexy, musky taste of her pussy there was a slightly bitter and salty one, which I assumed was my cum. I suddenly realized why a lot of girls were uninterested in swallowing a guy after a blow job. At first she just lay there, but when I cleaned all of the outside portions of her sex and drove my tongue deep into her vagina she made a small squeal and started contracting her vaginal muscles. Gob after gob of my gooey semen came out and I swallowed it all. The excited sounds and movements from both women made it easier to keep on.

"He's...he's getting it all...from inside too!" Mary panted in excited disbelief.

"Some young thing better snap you up quick, or else we might have to," Maggie added with a laugh, and started rubbing her pussy furiously.

It felt great to be willing to do something so simple that would make me a hit with women, but how does one go about advertising that fact to take advantage of it?

Mary's attentions to my cock and her arousal had me stiff again and I was ready to mount my aunt. Maggie turned around doggie style.

"Put it in my pussy, baby," she purred.

I remembered her remarks about babies and paused for a moment. But I was too horny and she did say not to worry about it. I slipped in and her warmth enveloped my manhood, rubbing and squeezing it just right. I began to think about the possibility of her getting pregnant. The risk seemed to heighten every sensation. I could imagine my sperm connecting with an egg in her, swelling her up. Would she even notice the baby bulge? Even so, I would know that my pleasurable act of cumming changed her body and her life. The risk of it all suddenly seemed scary and powerful all at the same time. Almost immediately I felt the spasms of ejaculation shooting deep in her pussy.

"That's it, baby!" she exclaimed, feeling it too, "Cum in me good, cum deep in me."

Maggie didn't cum from my efforts but seemed very satisfied with the results. We were all a bit exhausted lay in disarray on the bed, until Maggie pointed out that she had only cum once. It was true Mary and I had gotten off twice. I was pretty sure it would be a while before I could fuck again, and as long as Maggie didn't want my oral talents I didn't know what to do. Mary came to the rescue.

"Bob, why don't you massage her tits and I'll take care of things down here?"

I shifted position to rub Maggie's tits and kiss her. I kissed and sucked at her nipples some too, she seemed to like that. Mary was playing with Maggie's pussy, using smooth motions of her fingers to run all over her mound and delicately slip between the folds of her pussy lips. Maggie's breathing quickened a little and gradually the fingers moved more rapidly, curling around her clit and slipping into her vagina. Maggie started to make a continuous moaning sound and was soon shuddering all over. When her climax passed I saw Mary licking her fingers to taste Maggie's juices. Clearly Mary was willing to eat her, I wondered why Maggie was opposed to being eaten out.

After Maggie's climax, we all sort of dozed off. I don't believe any of us intended to spend the whole night crowded into the same bed, but it just worked out that way. I woke up in the middle of the night to Maggie stroking my cock. With a little quiet (we thought) shifting around she was soon sitting on top of my hips while I was buried deep in her pussy. Mary stirred and realizing what was going on, straddled my face without a word and settled her pussy over my mouth while she and Maggie kissed and fondled each other's tits. Mary was the first to cum, flooding my face with her lovely fragrant juices. Her climax triggered Maggie's, whose vaginal clutching squeezed out my, mostly dry, orgasm. Then we all collapsed into sleep again. A similar scene was repeated at least once more before dawn but I couldn't remember too well.

We showered before hitting the kitchen for breakfast. If the shower stall hadn't been so small I'm sure we'd have tried to take one together. As it was we took turns. I noticed that my dick was red and raw and swollen to about half hard. I'd never seen it like that. 

They were dressed casually and comfortably, but I was in my traveling clothes, it was time to fly back to Texas for the rest of my summer break. After a hearty breakfast of eggs, bacon and bagels they dropped me at the airport. There were deep kisses goodbye and hugs that seemed to last forever. Things had changed, but I was happy, and already looking forward to my next visit.


I next traveled to Long Island at the end of summer, just before my senior year started. There was a surprise when they picked me up at the airport. In the car with Mary and Maggie was a female naval officer in dress blue uniform, insignia of Lt. JG, perhaps late twenties with dark brown hair.

"Hi, Butch. I'm Charlie! That's short for Charlotte, but no one calls me that," she was a little brash and I didn't care for the nickname she'd adopted for me. On the other hand she was very attractive and outgoing and I wondered why she was there.

"I'm Bob," I answered with a smile to cover the emphasis I put on my name.

"Charlie is staying with us this week-end. I hope you don't mind. She's working on her resume so she can look for civilian employment," Maggie explained.

I had one of those unconventional thoughts I often have, 'what if I did mind?' Fortunately I'd already learned not to act on those thoughts. I had really hoped for a repeat of my last visit. Was Charlie's presence a nice way of saying that what happened was never going to happen again? Had I offended in some way, or were they just uncomfortable with the idea of fucking Maggie's nephew, where there was enough age difference to be her son?

"No problem," I answered. "So Charlie, how long have you been in the Navy?"

"Almost four years, and re-enlistment is coming up, so I thought I'd explore my options outside," she answered.

We made small talk on the way back to the house on Long Island. When our Q&A seemed to lag Maggie picked up the conversation.

"Charlie, I thought you would have a big date for this weekend. What's up?"

"I'm not seeing anyone right now, and I just didn't feel like burpin' 'em, if you know what I mean," she answered with a laugh.

I clearly picked up that the remark about 'burping them' was derogatory about men, but I couldn't be sure if it was only about the young men she knew, or all of us. I was beginning to wonder if Charlie was a lesbian; as in 100%, confirmed, man-hating or at least man disliking, dyke (though she looked feminine). My hopes for a weekend like before seemed to be vanishing before my eyes. I was beginning to wish I had simply flown to Boston and spent the time alone in my room.

At the house Mary suggested we take the boat out and I thought that at least with the roar of the engine and the splash of the waves it wouldn't be as awkward if no one spoke. I still didn't have a swim suit, but I did have some khaki shorts with legs almost to my knees I could wear on the boat. Charlie slipped into one of those one piece suits, but it was plenty tight enough to show off her B cup tits and a nice little mound between her legs. The suit was a dark blue with white piping trim around the edges. It looked prim to me, almost as if it were a statement against looking sexy, though that was undoubtedly just my prior impression of her working. The suit itself did not have bra cups under her breasts so the mounds were natural, and that was something you didn't often see even with bikinis.

On the boat I crawled up to the bow and made a spot for myself with a towel. Charlie soon joined me and we were lying on towels close together while the boat sped out into the water, the engines and waves making a strange rhythmic combination. She rolled over in my direction and punched my shoulder to get my attention.

"Your aunt tells me you're quite a guy," she said in a voice just loud enough to be heard over the din.

"Really? Well, she's quite a lady." This seemed different, so I continued. "I feel a little at a disadvantage. She didn't tell me anything about you."

"I'm direct, sometimes to the point of being bossy. And I'm used to getting what I want, though I don't mind having to work for it, or give equal measure." She smiled, confident that such a description wouldn't be off-putting, or perhaps just not caring about those who would be put off.

"That's succinct," I said, feeling that she had described my first impression of her to a T. But I was still trying to be polite and courteous, so I added, "Someone will always know where they stand with you. That can be a refreshing honesty, and a relief for the man who is often unsure of the signals he's getting from women." She smiled. I was just trying to see her attributes in a positive light, there was no further conscious intent on my part. Later I would realize what I said was just right.

There was no nude swimming off the boat this time, but there were cocktails, lots of cocktails with vodka. I paced myself, as did Charlie. Mary was a little freer with the drink, but no one could put them away like my aunt, and still remain functional. The conversation focused on the sort of positions Charlie was going to go after outside the Navy. It had something to do with ensuring the all the materials a business needed would be where they were supposed to be on time. In the military it was called logistics. The conversation seemed to flow naturally around me, as I had nothing to contribute. This allowed my mind to wander and it focused on my uncertainty about what was going to happen. I finally put it to rest with the thought that I'm sure someone would make it clear to me when/if the time came.

When we got back to the house Maggie and Mary declared they wanted to take a nap before supper and disappeared to their bedroom. As soon as their door closed Charlie took my hand in a firm grip.

"That's our cue," she said and led me to the guest bedroom which she had taken over.

In the bedroom I stared a little dumbfounded, still in my wet shorts and T-Shirt, she still in her swim suit. 

"Well take your wet clothes off," she ordered and when I began lowering the shorts she began to peel off the swim suit. "I don't do blow jobs, but I will play with it and maybe kiss it a little if I get real excited. I don't do anal and lucky you, my period is due in a few days so you can cum in me, but not till I say OK, so ask if you get close. Oh, and I'm a ballbuster."

"OK," was all I could manage to such a direct set of conditions.

"You do want to fuck me, don't you?" she asked almost a little taken aback.

"Oh, yes, of course!" I quickly answered realizing my surprise must have been taken as reluctance. "I was just caught off guard by your outspokenness."

"I did tell you I was direct," she added with a smile, lying down on her back.

I nodded while leaning over her to nibble at her petite tits. My cock had barely recovered from the cold water and was still a little shrunken. Her body was in great shape and her pussy was inviting, but I was only half hard. She reached out and took my cock in her hand. Without a word about my lack of stiffness she pulled it toward her head while I kissed my way down to her bush and swung into a 69 position with me on top. She stroked me slowly and tickled behind my balls. I hardened a little, and as I got my tongue on her pussy I stiffened more. The fragrance of her aroused sex was a potent aphrodisiac. I licked and suckled at the stiff clit buried beneath her hood and labia. She shuddered a little and her pussy was wetter. She held me tight for a moment, then squeezed my hard on firmly.

"Put it in me," she said breathlessly. She spread her legs and gave me the most enticing view of her love hole ready to be filled.

I put the head of my cock at the entrance and felt the wetness was enough to proceed. I slid into her just past the head. I thought I might do a few gradual thrusts to spread her natural lubrication over the length of my dick, but she put both hands on my hips and pulled me into her in one single thrust.

"Fuck me hard," she said through gritted teeth.

Her bossiness, and all her rules were something I didn't find completely appealing. I was turned on by strong women, and those who were sexually assertive, but in my inexperience Charlie was just a little too much for me at the time. That is a long way around to saying that I was just miffed enough to take her at her word when she said "harder!" I pounded her hard, our pubic bones colliding solidly on each thrust. She made a little squeal or grunt on each of my thrusts. My cock ached with the friction and force but I liked the idea of maybe hurting her a little.

I could tell she was getting wetter, and her pussy was clenching my cock tighter. Her sounds changed more to groans, like the build up to an orgasm. Her excitement was catching and I found myself building up to one as well. She hung at that high plateau of arousal for a long time, while I kept advancing. Soon I was in danger of cumming and she was clearly not ready to go over yet. I remembered her saying to ask if I was close.

"Are you close?" I asked.

"No, are you?"

"Yes," there was pleading in my voice, though I didn't actually ask permission to cum.

In an instant she pushed me out of her, grabbed my ball sack with her left hand, pulled it down and then punched it with her right hand. The pain was instant and traveled right up to my gut. I was suddenly no longer on the edge of cumming, but amazingly my erection was still pretty good.

"Quick, get back inside me," she instructed, while pulling my cock to her pussy. "Hard and fast," she said while her hands on my hips encouraged the motion. My balls ached with each slap against her butt cheeks, but strangely the sensations on my cock took away the pain in my gut. After several more minutes she tightened her grip on my back, her legs wrapped around mine and squeezed strongly. Her whole body started to shake.

"AHHHHHH. Cum when you're ready! Cum for me!" she shouted.

Her pussy clenched my cock like a fist, and something soft and spongy deep inside rubbed against the head of my dick. I couldn't stand it any longer.

"YESSSS! OH GOD!" I let out as I felt powerful streams of cum shooting into her.

As soon as our climaxes passed I pulled out and lay on my back next to her. Before I could think of something to say she turned to me.

"Well, you certainly lived up to your reputation," she said with a smile. That made me slightly uncomfortable thinking that Maggie and Mary had talked about me, but apparently it was all good.

"I suppose that's what you meant when you said 'ball busting'?" I said indicating my still sore nuts.

"What did you think I meant?"

"I dunno, demanding I guess," I faltered for a moment. That was the only context I had ever heard the term used before. She laughed.

"Works pretty good to bring a guy back from the edge of cumming, wouldn't you say?"

"Yeah, it did. Just out of curiosity, if I had cum without ..." 

"What you got would have felt like a 'love tap', 'cause I generally kick...hard; kickboxing Champ, Craney Island Supply Center and Norfolk Shipyard." 

I nodded, I could easily see that. Instead of an opportunity for me to eat her after sex, she headed off to the bathroom. Either our post sex conversation took away the mood, or Maggie and Mary hadn't told her about my other talents.

We all had dinner together and then the ladies got down working on the resume. I excused myself to do some reading. My nuts still ached, but it was hard to say whether from the punch or the massive ejaculation; probably both. I went back and forth between thinking that perhaps I was more seriously hurt than just sore, and wondering if she had ever caused a major injury to some guy. Consequently I made a lot of extra trips to the bathroom to examine my balls. Were they swollen larger than before? Is that the same color they were the last time? Is that too red, is there bleeding under the skin? Is that too dark, has blood flow been compromised, no longer circulating? I discovered a warm wash cloth made them feel a lot better and eventually decided that they really hadn't changed in size or color to any significant degree.

When it was bedtime, Charlie made no move to have me come to her room. I made the sofa into a bed and counted myself lucky as I was unsure I could take another punch in the balls if it should come to that. The next day she left. We exchanged pleasantries and said we hoped we'd run into each other again, but I sort of knew we wouldn't. At the time I was just as happy - even though the sex was good, it did seem to come at a high price. Today looking back I wonder what it would have been like to be with her for longer. Our styles were too different for a long term relationship, but I think I would have learned more about myself sooner with her.

I had another day with Maggie and Mary before I had to head back to school. My balls felt pretty good and I was really hoping that I could have sex with them again. Not only for its own sake, but also to verify that my balls still worked, so I could put the last of my fears to rest. We had just dropped Charlie off at the train station when Mary turned to me in the car.

"So how did you like Charlie?"

"She was fine," I answered.

"Fine? Well, we were hoping for more than 'fine'. I thought you two were having some fun in the guestroom," Maggie offered.

"Uh yes, we did," I stammered a little embarrassed but not too surprised that everyone knew, it was a small house.

"So was the sex no good for you?" Mary asked equally bluntly as Maggie.

"No, the sex was fine and all...but...well...she's a little rough and tough for me," I tried to explain in a non-derogatory manner.

"She hit you in the balls, didn't she?" Maggie guessed.

"Yeah, it was just to keep me from cumming too soon, but it really surprised me, and it hurt."

"We're sorry, honey. We just thought you might like having someone closer to your own age for sex, instead of us old maids," Mary answered apologetically.

"Oh, don't be sorry. I really appreciate you thinking of me like that. And Charlie was great in bed, it was just that she can be a bit..." I was just about to choose 'harsh' as the word when Maggie jumped in.

"Bossy," Maggie said. "Charlie can be a bit of a bitch, no doubt from making her way in the military, definitely a man's world."

"And I don't think of you two as 'old maids'," I said earnestly. "You are both so dear to me."

"That's very sweet, dear," Maggie said. "I hope our next plans for the weekend work out better for you."

"We don't want to seem too forward, but, well we invited a friend, closer to our age. It's been quite a while since she's been with a man," Mary offered.

"Now you don't have to do anything you don't feel comfortable doing," Maggie interjected. "It's just that you were so good with us, and we thought a young man like you might be open to more experiences like that."

"What she's trying to say," Mary said, "is that we figured a young man wouldn't be turning down an opportunity for sex under any circumstances; but if you do, turn it down, it's OK and we'll understand."

As strange and unreal as being fixed up by my aunt and her 'girlfriend' seemed, I really was excited about the sexual opportunities. I was a little embarrassed that they had bragged on me so much, and that made me worry about living up to what they had said. Then I realized that if I just did what I had already done with Mary and Maggie last time, I should be fine. And in any event, if their friend hadn't been with a man in a while, how good did I have to be?

"Ruby isn't anything like Charlie," Maggie said, apparently thinking my silent ruminations were about that. "She'll want you to take the lead."

"Sounds good! Let's do it!" I said with genuine enthusiasm. Somehow I knew that if I had turned down even the Charlie experience I would regret it the rest of my days. Mary and Maggie were obviously relieved and pleased.

Ruby showed up at the house just after noon, and we all gathered in the den for drinks. She had red hair which was enhanced with a rinse of some sort. She was about Mary's size. I don't remember much about the conversation, it was mostly mundane small talk past the initial introductions. Then when the conversation started to die down, Mary moved next to me and kissed me full on the mouth. I kissed back and the next thing I knew she was undoing the buttons on my shirt. I began undoing hers and soon Maggie was there too. I was kissing first one then the other and I didn't even notice that Ruby had removed everything except her bra and panties. She joined in the kissing and caressing and removing of clothes until all four of us were naked in front of the fire place. Ruby got down on her knees and started kissing my cock and balls, while Mary fondled them. Ruby even tried to stick her tongue down my piss hole. Maggie was standing next to me while I kissed her and hefted her tits.

Remembering what Maggie said about Ruby and taking the lead, I gestured to her to sit back on the hearth. She spread her legs wide and I got ready to put it in her.

"Don't cum in me," she said nervously. "It's not my safe time."

I was tempted to tell her I doubted I could father children after Charlie's cure for getting to close to cumming, but I didn't. She seemed so genuinely concerned.

"Should I be using a rubber?" I asked, even though I didn't have one.

"No," she shook her head emphatically. "That would be wrong. Just try not to cum in me."

I didn't try to figure that out at the time. I was hard and wanted to see what Ruby's pussy felt like. I had to trust that I could hold out like I did with Maggie and Mary. Maybe she'd let me cum in her ass.

She was already wet and my cock slipped into her with ease. She was tight, like Maggie and Mary had been, and I realized that was probably from lack of sex, or at least sex with penetration. I also realized that it was probably a good thing I wasn't huge. Watching porn and reading erotica it was easy to get the idea that women only wanted the biggest cocks. These ladies wouldn't have been ready for a beer can sized dick.

I was enjoying the feel of Ruby's love tunnel and having no trouble staying away from the edge of cumming. She was moaning and squealing while getting used to having something in her pussy. Suddenly she was jiggling all over and making a high pitch whine. I realized she was cumming as I felt her get a lot wetter and grind down hard on my cock, pushing it deep inside her. 

I imagined the little pucker of her cervix hitting the head of my cock. I even wondered if it was possible to force that entrance to her uterus open wider with the head of a penis. If I had cum then there would have been no question that some of it would have gotten in her womb. As I pulled out still hard she realized that I hadn't cum and was trying to get a lick and kiss on my dick. Did she secretly want a child too? Or was she hooked on the risk of pregnancy? Or something as simple as religious prohibition on birth control?

Maggie bent over and showed me her sex. I put my cock at the door to her pussy and slipped it all the way in on a single thrust. She grunted with satisfaction and began to move that big ass of hers in a very sensuous fashion. I was enjoying the gradual ramp up of excitement.

"Cum in me!" Maggie shouted in a sort of desperation. "Cum in me now or I'll get Charlie to come back and squeeze it out of your balls!"

The pain of Charlie's fist hitting my tightly squeezed balls came back in a flash, and before I knew it I was spewing huge streams of cum into Aunt Maggie's pussy, and I didn't even know where she was in her cycle. Based on what she had told me the first time, I guessed it didn't matter.

Mary had been eating Ruby's pussy and I suspect getting hers done as well. Maggie sat down on a chair and Ruby leaned over to kiss her while Mary sat on the floor and still worked at her pussy. I thought I had a great way to keep myself hard. I took some of the mixed cum and pussy juice from the head of my cock and rubbed it on Ruby's asshole. She pushed it out toward me and I started pushing it in slowly. She moaned a few times as it inched its way deeper. Mary kept up a constant rhythm on her clit making it easier for Ruby to tolerate the penetration. Her tight ass and the periodic clinches she made with it were keeping me hard and rapidly moving me to another climax. I recognized the sounds of Ruby's impending orgasm and that put me over the edge. I could feel powerful ejaculation spasms but there was little cum, and my balls actually ached from the effort. I lay down on the floor exhausted. Mary and Ruby began to massage my balls, and I motioned Mary to put her pussy over my face so I could taste and smell her delicious sex.

Ruby went from massaging my balls to gently sucking them into her mouth and using her tongue to caress them softly. Maggie had moved from her chair and was kissing and fondling Mary. It was wonderful, but my cock wasn't going to get hard for a while. That didn't deter the ladies at all, but eventually we all sort of agreed that I would need a bit more recharging time.

We all had our drinks refreshed, but no one made a move to get dressed. I assumed it was because we all expected to resume the festivities soon. But after a little bit of mutually complimentary remarks, Mary and Maggie excused themselves to go to their bedroom. In a move I had to assume had been planned by the ladies from the beginning, Ruby moved over to me and suggested we go to my room.

Once there she resumed sucking on my balls and tickle touching the spot just behind them. I signaled her that I wanted her pussy over my face, and she obliged, and assumed a 69 position. Somehow she managed to do this without removing my balls from her mouth. Now I had a perfect upside down view of her pussy. Her clit was at my lips and my nose was buried in her vagina. Oh that sweet aroma was the most powerful aphrodisiac for me. My lips worked her clit and sucked on her labia, again pulling on her clit and she got wetter, while making the most erotic little squeals deep in her throat. I could feel my erection growing, yearning for stimulation. She could tell as well, and plopped my nuts out of her mouth.

"I want to cum on your cock again. Put it in me!" she said with an urgency born of still unsatisfied lust.

We shifted positions and I slipped into her balls deep in a single thrust. The rest had restored my functions. We moved with ease for several minutes, she bucking up to my inward thrusts. Her eyes were squeezed shut and her face was in an intense expression of concentration. I could feel her tightening her pussy on my dick. She was ramping up to her orgasm. But the intense pressure in her vagina was bringing me along a lot quicker.

"I'm getting close to cumming," I said to warn her I might need to pull out suddenly.

"Don't cum in me!" she said desperately.

I tried to slow my thrusts but she was controlling the speed and depth with how much ground her hips into me.

"UH UH UH" she grunted teetering on the edge of orgasm. I was being pulled closer and closer to the edge. I hated to disrupt her orgasm but I knew I wouldn't be able to hold out any longer.

"I've got to pull out! I'm gonna cum!" I said urgently.

"NO! Don't pull out! Just a little longer!" She tightened her legs around mine and grabbed my hips with both hands.

"Oh NO GOD!" I actually whined as I could feel my recharged balls dumping a big load in her fertile pussy. Her orgasm began and she shook all over and made that high pitch whine. In a few moments my cock deflated and slipped out of her, along with a large glob of semen.

"Oh my God! There's so much of it!" she said with panic in her voice.

"I'm sorry, I tried..." I started to explain and apologize, but she cut me off.

"I know, you warned me, I wouldn't let you out." She squeezed my hand calming for a moment. "But it was so good!" Then shifting back to worried and agitated she hopped off the bed and went into the bathroom with her purse.

I got dressed and could feel a knot developing in my stomach. What if she got pregnant? If she wouldn't use condoms an abortion will certainly be rule out. Would she expect me to help pay for the baby? I was rapidly feeling sick. Ruby and I had an awkward silence between us until she left. As she was leaving we kissed and hugged, and she whispered in my ear.

"I'll let you know."

Then she was gone. What did she mean by that? Well obviously she meant..., but what about if she is pregnant? Maggie and Mary picked up on the fact that something was wrong right away. I explained the whole situation in probably more detail than necessary, right down to the lack of any direction if she became pregnant.

"Sounds like you did everything you could, she forced you to stay in her until..." Mary said letting the last just hang in the air implied.

"She's not gonna get pregnant. Don't worry about it. And she definitely doesn't want you to marry her," Maggie said.

"But what if she did?" I asked plaintively. I was too much of a scientist and worry wart to take a simple assurance.

"Well if she needed any money to get the baby up for adoption I'll help out with that, but she's not going to get pregnant," Maggie asserted again.

"How do you know that," I persisted.

"OK. You're a smart guy. You know how the testes work. They make sperm and they have to mature before they're ready. You've cum so much in the last couple of days that there should be virtually no mature swimmers left. Plus, did she go to the bathroom with her purse right after?" Maggie asked with a knowing twinkle. I nodded. "She was douching out."

"Then why did she seem so worried?" I asked. Maggie laughed her big hearty laugh.

"Because she's a worrier. That's what she does. She loves it. She'll fret about this for two or three weeks, reliving the sex every time. Then her period will come and instead of being pissed that she has to deal with ole' Aunt Flo, she'll be relieved and grateful for another week. Hell, you've just guaranteed the women three or four weeks of enjoyment."

We all laughed about that and had another drink. The next morning I had to leave for school, my senior year. It was a busy year and I never got back to Long Island. Graduation came and I was dashing back to Houston to find a job in a down labor market. I would never spend another weekend with Aunt Maggie. We'd stay in touch periodically, but there never were any more sexual encounters. I am grateful for all I learned about women and love during that time. I see now that it was more valuable than anything I could have imagined.