I was always a sexual boy growing up in a lower middle-class neighborhood in Boston. I grew up in a long line of two and three story homes. In cities, these are common, with each floor a separate apartment of six or seven rooms. My father had died when I was 3, and my mother was a hard working woman in the shoe factories. We and my three older siblings lived in the large apartment above my grandmother in her house. It was a large house with attic and cellar. There was no front yard to speak of, and the road ran up a hill towards my house and by the front door. Plots were close, and houses separated by a driveway only. Back yards were a little bigger, with hedges or fences separating neighbors’ lawns and gardens.
This story begins when I was about 13 or 14. I was a thick boy with some baby fat on my six foot two inch wide-shouldered frame. Dark brown hair and glasses framed my clear complexion. I only knew my lips were full and nice because an older girl at school turned to me on the stairs one day. She spoke to her girl friend beside her and said, “Now those are kissable lips!” as she looked at me. I blushed and looked down; the moment and the girls were gone in a flash before I could think what to say. But I remembered. Another time in my painfully shy adolescence, a voluptuous classmate nearly gave me a heart attack when she ran onto the basketball court during intramurals and patted my ass in front of everyone! I never followed up with that flirt either, due to lack of confidence and my assumption that my fat body, plain-brown eyes, nerdy glasses and brown hair were just too unsexy.
I was still clueless about what girls were about, outside my fantasies based on what I gleaned from movies, TV commercials where women wore bras over sweaters, and National Geographic photos. I was lucky enough to find two old Playboy magazines, but they were of a vintage that showed impossible breasts and legs demurely crossed so no vaginal lips existed. I had discovered masturbation the year before when I found my older brother’s Playboy magazines in the basement, and furiously pumped my cock five or six times a day to keep the tension at bay. Everything seemed to find my cock straining to get released from my pants, sometimes causing great Catholic guilt and embarrassment.
This leads me to write about, in an ungainly fashion, Eric’s mother Mrs. Cohen (not her real name). Eric was my next door neighbor, handsome, Jewish, athletic and a genius. We chummed for years in the neighborhood after school. We went to different schools due to religion, but we didn’t care about that at all. Other kids made fun of him because of his looks (I later found out as a man he was gay), his brilliance, or his being a Jew. His family was the only Jewish family in a sea of Catholic homes. The houses sat all of 40 or 50 feet from each other. Eric’s parents lived with Eric and his autistic brother in one upstairs apartment opposite ours, with his grandparents in the downstairs apartment opposite my grandmother. His brother went to a special school, even on weekends many times. His father was a mean drunk who spent his time working or hanging out at the bars. It was an unhappy family, but somehow Eric and his mother always had a smile for me, and we got along famously.
One summer day a couple months before my story commences, Eric and I had been comparing each other’s penises behind some trees. No sex, just curious comparison. Later we were in his kitchen getting some milk when Eric mortified me by telling Mrs. Cohen, --his mother and my neighbor, “Mike’s penis is a lot bigger than mine.” I almost spit up, but she was cool about it and mumbled something about it being nobody’s business. But at that moment I noticed her as a woman and not just as “Eric’s mother.” Over the coming weeks I glanced at her during the usual comings and goings, and started seeing her in a sexual way. She asked that I call her by her given name, Martha, as Mrs. Cohen made her feel old, and she said I was getting big enough to call her by her first name. Martha was in her late 30’s, certainly no more than 40. She had dark wavy hair to her shoulders, a bit of a tummy after two children, but not fat. Her breasts were soft in appearance, full and jiggled a bit when she laughed. Her hips were wide but slid in a comely fashion into shapely legs and her ass was nice to imagine about under her skirts and pants. Martha, as I started to think of her, was coming into my fantasies more often.
Each summer Eric went to a Summer Camp for a couple weeks. It was during this time I was bored and given chores to do. As was her habit, Martha sunbathed in the small back yard abutting ours. I was cutting my grandmother’s small patches of lawn among her raised rock gardens. Only a hedge separated me from surreptitiously ogling Martha. She was alone in the back yard, with family all gone. She was lying a few feet from me on a folding chaise lounge. My sweaty body was pushing the hand mower and separated from my fantasy by only some low hedges. She wore a rather scandalous (for those days and that neighborhood) black bikini. She lay on her back with the top straps rolled down and the cups pulled as far off her breasts as possible for maximum exposure – though her nipples were covered.
Looking back, I’m sure she knew I was watching her. During a pause in my work she opened her eyes and said hi. After pleasantries she asked me to come and chat.
“Have a seat, Michael.” She said as she scooted to make room for me on the chair.
I was grateful to sit because I had a raging hard-on in my shorts. “How are you Mrs., er Martha.” (Witty wasn’t I?). We chatted about things I no longer remember, likely how Eric was and where was everybody (both houses were empty). As we talked Martha did not attempt to re-cover her breasts, but held a cup to one globe to hold it in place. As we spoke I saw her pussy outlined in her bottoms, with some dark hairs escaping from the sides. My dick was aching and throbbing in my summer shorts.
“Michael, I want you to know I let Eric know that telling me about your penis size was not cool.” I turned red as she added, “It’s OK not to talk about it, it is natural for boys to explore and be curious. But Eric shouldn’t have embarrassed you.” There was a pregnant pause and she asked if she should not have raised the subject. I mumbled no, looking down.
“Michael, you are a sweet boy, it is OK to wonder about sex.” “If you want to ask me anything, it’s OK.” I of course said nothing, but she asked if comparing my penis to Eric’s had satisfied my curiosity.
Feeling brave, I asked, “Why does Eric have no skin at the end and I do?” I thought, Oh! God, what did I just say? But Martha just took it in stride.
“Jews have a ceremony called a Bris, when a boy is young. All Jewish boys are circumcised. Gentiles don’t always have that done. But God made us all in his image, so it doesn’t really matter in the end I think.” After a pause, Martha asked, “Are you curious about anything else?”
Her openness was so different from my strict mother or the nuns at my school, I think I just felt comfortable that warm day. “Sometimes I touch myself and it feels good, but I’m afraid I do it too much or it will be bad for me.” She smiled, “Michael, most people touch themselves.” The ‘people’ nuance did not escape me. But I wondered how girls did it without a penis – I was so naive. She added, “Sex is special and hopefully loving when a man and woman can give great joy to each other, but when we are alone or have nobody in our life, playing with our private parts is a good way to feel better.” “How often do you masturbate?”
Oh God, I think I was turning into flames, I was blushing so hard, “Most days 3 or 4 times, I fibbed, but one time it was ten times.” She sucked in a little air and her breasts stood out with the breath.
“Well it seems everything works then!” She said, smiling, “Don’t worry about it Michael.” “What do you think about when you play with yourself?”
Now we were getting in uncharted territory. I wanted to tell her I hadn’t seen a pussy since little Annie showed me hers at 6 when I showed her mine at 5, nor did I tell her I dreamed of “my” Martha’s love box encased in dark hairy mystery. Instead, I said “Well I found a couple Playboy Magazines my brother left in the house before he moved out, so I look at them. Sometimes I think about girls I know.”
“Anybody I know?” she asked
“Once I thought about you.” Who the hell said that!? It wasn’t me, it couldn’t be! I wanted to die.
Martha looked at me, I think – my eyes were checking out the leaves of grass between my feet. I could feel her dark eyes on me. “Would you like a cool drink?” she asked as she tied her top.
I was saved! “Sure.” Maybe she didn’t hear me. Maybe she won’t tell my mother I’m a pervert. I could barely stand the conflict of guilt and extreme sexual tension.
We got up and Martha led the way to her back stairs. I followed her, looking at her ass wrapped so tightly in the bikini material flexing as she walked up the spiraling stairs. My cock was leaking and I looked down. A wet spot. Jeez, just what I need now. I tried to think of Carl Yastrzemski statistics; the Red Sox were the least sexy thing I could think of. No good, her ass kept waving at me saying ‘hi’.
In the kitchen, she bent into the cold refrigerator and asked if I wanted some lemonade. She popped up and poured two glasses. As she turned around I saw her nipples straining the black fabric. Her large C breasts were slightly sagged but full and the curves of her cleavage were directing my gaze to the two prominent nipples pointing at my chest.
After a sip she said, “Michael, you look uncomfortable. You can’t stand still and you have a pretty large erection – Don’t be embarrassed, please! I take it as quite a compliment.”
I was shy and speechless. She said, “Maybe I can help just a little.” And then she did the most amazing thing. She reached behind her, said, “Don’t tell anybody I did this.” and undid her bikini top. She lowered it and took the bra off. She stood there smiling as I soaked in every detail, every nuance. I took in the freckles in her cleavage, the quarter-sized areola. Her nipples were the size of my pinkie end joint and the whole thing was crinkled. Her breasts sagged only a little. There was one blue vein that made them so much more real than the faked ones in the magazines. I stood there numb and speechless.
“Can I touch them?”
“I don’t think we should do that Michael, but when you masturbate, it will be OK to think of me. I don’t mind. Do you think this will help until you get a girlfriend?” I nodded dumbly in response.
I don’t remember anything else about that day or how I got back home. I just remember staring at the most beautiful breasts I had ever (literally) seen. But the next day, I looked out my bedroom window, and Martha was across the way in her kitchen washing dishes in the sink. The kitchen windows were directly across from my bedroom windows. My shades were partly down and I could only see her from the waist up as I lay on my bed. She was wearing a plain white blouse with a couple buttons undone. I imagined I saw the swell of her cleavage. I felt so sexually aroused looking at the woman who said it was OK to play with myself. Looking at the woman who said it was OK to think of her.
Emboldened, I took off my shorts. My seven inch thick cock with sparse hair around it sprang above my small tight ball sack. I rubbed my legs and cupped my balls. Just then Martha looked across the space between the houses and saw me. She MUST have, because she stiffened and stopped drying the dish in her hands. I slowly stroked my cock, daring her to watch me. She stood there, silently. I stroked slowly, enjoying the feeling of my hand, thinking about Martha’s full breasts in front of me: imagining Martha washing dishes in the nude. I felt the pre-cum on my tip and spread it with my thumb. I felt my balls with one hand and stroked my cock, feeling the veins bulge. Martha put the dish down. If we had talked loudly, we could have spoken to each other, but we said nothing. She licked her lips. I saw her right hand go below the sink and her clothes rustled. I couldn’t be sure, but I think she was playing with her pussy, watching me beat my meat.
I groaned and then picked up the pace. It was my first cum of the day and I wouldn’t last too long. My cock throbbed in my fist and squirted thick ropes of cum up above my head, hitting the headboard. More cum spurted and hit me in the face and chest, finally dribbling onto my belly. I held my breath and electric tingles ran down my arms and legs; time stood still as I locked onto Martha’s eyes and tits. My legs had stiffened and toes curled. It was the best cum I had ever had.
Martha was watching me. I could see her frig herself by the movement of her arm, the rusting of her clothes and the jiggling of those magnificent tits. I lay there drenched in cooling cum all over my face and chest as I saw Martha support herself with one hand on the sink edge, and then her mouth opened in an O and she shuddered. A pause and she looked away, and then closed the shades of her window.
Nothing was ever said between us. Once more a few days later we had our mutual masturbation play on our private stage. But after that second time, although I tried to show myself on the bed, she closed the blinds in her kitchen window. Nothing ever again was ever said or done that was sexual between us. I have my suspicions she felt some regrets, but I don’t know. I felt lust, pleasure and thanks for this supportive woman helping me.
