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.