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.
