Northside Awakening

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When I think about Kristen, I remember stunning blonde-white hair, her continuous sex drive and sexual confidence, and the way she approached exams like the Olympics. Kristen was a serious student, an attractive and attentive lover, and a good– if dull– person. Our college relationship was my first and her fourth. Even though I was a year older, she appeared to be my senior in all respects.

Kristen picked me out of a crowd at a party and seduced me before I could talk myself out of deserving her. After inviting me to her room on a pretense, her shirt was off within half an hour. I had gotten this far a few times, but not in the first couple of hours of acquaintance. Nor had I experienced stroking and sucking tits that were as beautifully shaped and pleasing. Her nipples soared upward from her medium size breasts, and Kristen moaned in response to every touch—light, rough, squeezing…whatever. Although I didn’t know it at the time, she would be the easiest lover I have ever had. No matter how you tried to please her, it worked. Her sexual zone was generous and her needs obvious.

I returned to my room three hours later in a happy, anticipatory state. Perhaps my virginity and I would soon be parted. Within the week I received and gave my first oral sex. She led me to the joy of tonguing my partner to orgasm in a forest of light yellow and exceptionally fine pubic hair. I think back on licking Kristen with delight whenever I see a woman with that sort of unusually blonde mane.

Within two weeks my virginity was blessedly gone. I suspect she knew it was my first time. We never talked about it—that wasn’t our type of relationship. It was about as good as I can imagine given the awkwardness of the situation. She put on the condom and softly told me how much she needed my hardness inside her. She made me feel competent, as if I had done her the favor of my sexual gift. I’ll always love her for that afternoon. We made dinner together afterward, then fucked again. The second time was even better—more animal-like and intense. Our bodies were getting to knew each other by then, and intercourse was the big frontier I was crossing with her.

Despite our beginning at her direction and charge, it was me who broke it off six months later, just before graduation. Kristen was a conservative Christian and a controlled person in every way except in bed. It amazed me how she compartmentalized her right-wing religious views and her guilt-free sexual pursuit. But when we ventured into politics, life after college, careers or anything else, it was clear that we were careening in opposite directions. We were from the same type of family of origin, but by the end of college I was well on the way to becoming what I became: an urban, left-leaning, agnostic bicycle rider. Kristen never stopped being what we were raised. And she probably has one happy and sexually fulfilled CPA of a husband by now. I hope so anyway.


I went to medical school after college. The third year routine was in place when I heard someone behind me in the Saturday morning line at the Daily Grind Cafe, “Jake? You probably don’t remember me, but I’m Anna, a friend of Kristen’s from Ann Arbor.”

“Anna Fuller,” I replied. “You had this cool hand-knit red and purple sweater you always wore, you sat three rows behind me in World Music, and you use to date that creep with the big biceps, Chester something…Or, at least I hope it is a used-to date situation,” I bit my lip in mock anticipation of being wrong, although I thought that highly unlikely.

“Creep doesn’t get half-way to that bad choice. And, hey, I guess you do remember me,” Anna said with more than a hint of being flattered. “What brings you to Chicago, other than the giant magnet that draws in about half of us leaving Ann Arbor.”

“Medical school. Someone told me that I had messy handwriting and would be a natural at this. I’m in my third…” Just then two of Anna’s friends came into the shop, obviously in a pre-arranged meeting of their group.

“Mila and Alyson, this is Jake Lindman. He was the boyfriend of a friend of mine at Ann Arbor.” Anna finished introducing us and graciously transitioned to small talk that had all of us feeling comfortable. When things started to wind down, she asked if I wanted to join their group discussion at Alyson’s house. “We have a bible study and religion discussion group on Saturday mornings. I know that doesn’t sound like much fun, but we talk about lots of stuff. We include strays all the time.”

As unexciting as that sounded, I rarely turn down the opportunity to spend time with three pretty, young women. Alyson was stunning—perfect breasts with just visible nipples, narrow waist and flawless, delicate features. She had hints of freckles around her nose. Her legs seemed to start about an inch south of those ideal breasts and slope down forever to her carefully selected and stylish shoes. She could have any straight guy on the north side of Chicago, or any other city.

Anna was pretty in the way that most 23 year old women are pretty. A touch chubby, glowing skin and a winning smile. Gaziantep Escort İlanları Anna’s looks were all the better paired with her inclusive and warm manner.

But it was for Mila that I said yes to bible study. Alyson was out of my league and I sensed out of my comfort zone, as well. Anna didn’t excite me enough to get over that mountainous cross between her huge breasts. And her friendship with Kristen was a cut wire I would rather not reconnect.

Mila, however, was strangely and intensely attractive to me. She was medium height, on the thin side of average and had tiny lumps on her chest; breasts so small that a bra was almost irrelevant. She had wiry arms with a hint of shop-guy muscles. Her ass looked to be about perfect. She had on shorts that showed off her nice legs. Mila’s long, brunette hair was pulled back in a no-nonsense pony-tail.

Mila dressed in an eclectic style, with yellow Chucks, jean shorts and a red top with a small graphic in yellow– a tear drop over an abstract shape. Her glasses were small, East Village sophisticated. Mila had a slightly shy way with an obviously quick wit. Hard to describe, but just an out-there style mixed with rather nerd mannerisms. I really like smart. She seemed bright and curious, on first impression. And how this all fit with post-college bible study I couldn’t quite manage yet.

I trailed back and conversed with Anna while Mila’s perfect butt preceded us by a few steps. “So, what’s the subject of bible study today?,” I asked out of curiosity about the proselytizing hell I had agreed to join.

“We just open the bible randomly and read a bit and talk,” Anna replied to my delight. That seemed like something Kristen (or my aunts or anyone else back home) would never have had the spontaneity or initiative to experience.

“Sounds like a good program. I have to admit that I have strayed a bit since the time I was dating Kristen,” I said, trying to soften the way for at least a marginal amount of my truth to come out during the next hour or so.

“Since Kristen described you as her lovable heathen, I can’t imagine you’ve strayed more in the last couple of years,” Anna offered in a teasing and accepting way. “It doesn’t matter. We are not quite as devout as Kristen, although- like her- we all have pledged to stay virgins until marriage.”

I was speechless– stunned how much and how well Kristen had hidden herself from her friends. Kristen was about as virginal as the average 35 year old bar waitress. We crossed Clark Street, and we headed up Rousseau to Alyson’s apartment. Compared to my dump, we were up five rungs on the income ladder. This beautiful woman had serious money, too.

After settling into meeting mode, Alyson took leadership and opened the bible to a part that included a familiar quote: “Finally, brethren, whatever is true, whatever is honorable, whatever is right, whatever is pure, whatever is lovely, whatever is of good repute, if there is any excellence and if anything worthy of praise, let your mind dwell on these things. [Philippians 4:8].” I mostly sat silent while these young women shared parts of their lives. They seemed a bit tense with me there, but eventually got more real. Mila was amazing. She was more than just smart, and really introspective. Alyson, predictably, was the least reflective, but well-intentioned. Her remarks basically can be summarized as a Dale Carnegie hymnal. Anna was honest and had an open heart. As the only male, a closet (then) agnostic and the newcomer, I tried to be unobtrusive. Mila called me out.

“Jake, I understand this may not be the easiest setting for you, but what is true, honorable and pure and lovely that you want to dwell on?”

My first instinct was to say, “your nice-looking butt, Mila.” I thought of being glib—not appropriate. How about ducking it with banality—no, I wanted Mila to think me not shallow. Maybe I even wanted to be not shallow. So I tried for the best part of the truth that occurred to me at the moment. “I guess I don’t believe in being right and pure. I believe in being kind and gentle and respectful to other people and the earth. I mostly believe in being alive and focusing on now. I don’t think there is a heaven for believers or a hell for the wicked, so I don’t care if I am abstractly good by some standard that makes no sense for the life I can sense.”

I thought that would pretty much end the morning for me, but it did the opposite. All three came alive in different ways. Alyson wanted to do battle with my ideas. Anna just wanted to drop off the burden of being good that she had been carrying around like rocks in her pack. Mila wanted to fuck me. I saw it in her eyes as soon as I looked up from talking. And I wanted her to know I wanted her.

We talked for half an hour or so, then Mila steered the conversation toward the direction of sex. “What about nudity? What’s wrong with that? Some days I feel so oppressed by this God who has been drilled into me my whole life. I’m 23 and I’ve never seen a guy naked. I’m not sure that’s so good and pure.”

Alyson was shocked, but Anna jumped on the theme. “Me, too. I’ve never even done more than kiss a guy. I used to wear that as some badge of honor, but now I just feel lonely and…” She was searching for words. Mila went for the guts: “horny?” “Yeah, horny,” Anna said with blush rushing over her face. Then some giggles by both of them.

I found this conversation both a little sad and a lot erotic. These women were pretty old to have so little experience with men (let’s just assume they were more honest than Kristen—I think that was the case, but maybe not so with Alyson). The atmosphere of intimacy was building the sexual tension. I was trying to hide my growing erection when Alyson even joined the crowd, “I know people think I turn away date offers all the time, but actually everyone considers me just too uptight to ask out. My only relationships have been with a guy on his way out of the closet, some guy who tried to jump me on the second date and Walter.” They all nodded in a tsk-tsk at the mention of Walter, and I just let that be.

I had an idea (or was this Mila’s idea I was channeling?) and I decided to go for broke. I figured the worst thing that could happen was avoiding The Daily Grind for the next few Saturdays. “Since I broke up with Kristen I’ve had a couple of relationships. I’m not a virgin anymore.” This, of course, was a literal, but highly misleading, truth in protection of Kristen. “I know it may be different for a guy, but I like having sex. No apologies.”

Silence. Why not go on as long as you’ve tanked anyway, I thought. “If you want, I will get naked for you so you can see what a guy looks like.” I was rushing the words and looking at my feet as I continued, “but I’ll warn you that being around three women as attractive as you means I’m probably going to have an erection with you staring at me.” I looked up at Mila as I finished. I knew immediately we were thinking along the same line.

Mila let Anna talk first. “Jake, I would appreciate seeing you and anything you will show us. It’s a lot safer here with the three of us and you than some of the alternatives.” “Me, too,” quickly joined Mila. Alyson held back. “Jake, I don’t know. Maybe I’ll go in the other room while you show,” she slowly announced. “Of course, whatever you are comfortable with,” Mila said.

Alyson got up and started to the kitchen, then turned around and sat back down. “Oh, why not. I should have done this awhile ago,” she declared, throwing out her caution. Everyone laughed and much of the tension was gone. My erection had wilted in the process of negotiating this and I figured now was the time to go for it. I’m no beauty, but I’m proud enough of my body. Given the lighter mood, I went for a somewhat striptease effect. The three women started hooting…all of us enjoying the campiness of it, and all of us aware that I wasn’t a Chippendale and they weren’t middle aged housewives.

When I took off the last of it, I was starting to get hard again. Mila, Anna and Alyson grew silent watching my dick extend out to a full erection. I was aware of every breadth as I saw three attractive women staring at my hard-on. They were in a semi-circle in front of me, and I walked nearby so they could look closely at me. I kneeled in front of them. It was intoxicating for all of us.

“You can touch it, if you want,” I suggested. Mila reached out to stroke me a few times. It was electric. Alyson did the same. I maybe was her first hard-on, and she will likely remember that forever. Anna was the boldest. She reached underneath and lightly touched my balls. “Is this OK?,” she wanted to know.

“It’s more than OK. It’s wonderful. All of your touches feel wonderful,” I said looking at Mila. Mila moved over and kneeled in front of me. The other two followed. All three started stroking my balls and dick and passing their hands over my dick’s engorged, red-purple head. Between deep breaths and genuine pleasure, I explained pre-cum, that I was circumcised and the rest of the basics.

“Can I teach you to masturbate a guy?,” I asked hopefully. I didn’t need to wait for the yes responses. I started to stroke myself. Then I grabbed Mila’s hand and taught her to run her grip down the length of my penis, adjusting the tightness when needed. Each had a turn.

After a few minutes I started to feel the urgent building of a climax. I got Mila to take over because I was connected to her and wanted her to be the one who got me off. I asked everyone to move away from my front as I was getting ready to cum. Mila was pulling on me in nice rhythm by now. I could feel the orgasm grab me and I ejaculated across the room. Three good loads and some dribbling of cum. I was spent. When I looked up, three pretty women were staring in amazement at the trail of white in front of them across the hardwood floor. I looked at the faces of heightened senses and felt an ego boost that I was still riding at New Year’s.

A cleaning-up, getting dressed and such later, it was about five minutes before we really started talking again. I was trying to make sure everyone felt OK. Alyson was slipping in and out of fundamentalist guilt, but Anna was pumped, while Mila and I were trying to figure out how to be alone together.

“That felt incredible. Thanks to each of you. I’ve never done anything like that,” I said. “I doubt I’ll ever have three gorgeous women touching me at the some time like that ever again.” All three said they were really happy to have learned so much about sex.

We had some food Alyson put out and talked about subjects other than sexual frustration and nudity. Alyson started to look at me with some real attention, but that wasn’t going to happen. Even up, I wanted Mila. Bright, intriguing and flat-chested Mila. I gave everyone a hug and started to walk toward the door. Both Mila and Anna said they were leaving, as well. We all headed for the L stop at Belmont. I grabbed a hand of each as we walked.

The three of us probably looked a bit of the ménage-a-trois we sort of had been as we stood on the old wooden platform. Anna was heading back toward the Loop, which is where I needed to go to accomplish some work. But I lied and said I was heading north on the Ravenswood line—Mila’s direction. I hugged Anna as her train came rattling in and she was whisked away toward Lincoln Park and downtown. I was a bundle of positive nerve endings as Mila and I embraced in our first kiss, oblivious to the fellow El riders and bound for a bright Saturday afternoon journey to the farther reaches of the north side.


I don’t remember much about that train ride other than Mila’s tongue and mine exploring in the empty seats we scored in the back of the train car. Her bare legs were intertwined with my chinos. Each time she rubbed against me, a jolt went through to the erection straining my pants.

Her tiny one-room apartment was two blocks off the Western stop, just behind one of my favorite restaurants, Mella Sera. She had the attic. It was hot up there, so she broke away long enough to open some windows and turn on some fans. That gave me a chance to take in a pleasing living space. An unframed poster of the Lakes District in Britain or such; original artwork of high quality I later learned she had painted and placed all over; a vase with one stalk of asters (picked off an alley stray) on some hand-built pine shelving that contained her clothes; and maroon painted walls. The one thing you would not call it was uptight Christian.

When she came back to me I pinned her into the bed with my erection pressing in the middle of her shorts. We were kissing, but hesitation had infiltrated our pleasure.

“Mila, do we need to slow down a bit?,” I offered.

“No. I’m just so excited being with you, and this is all so quick, and I’m scared I’ll do something I regret—too soon anyway.” She finished with a mostly anxious look at the floor.

“I totally understand. Are you really a virgin?,” I gently asked.

“Yes. I wouldn’t lie to you,” she said with more sincerity than offense. I’ve never gone beyond kissing with a guy until I held your penis today. I’m so ready for sex I’m going to explode, but even though I’m 23, almost 24, I’m still all mixed up about it.” Her pain and confusion were palpable. Her honesty endearing.

“I have an idea. I’m your sex waiter. Here’s your menu of erotic ventures du jour. For an appetizer, we have holding hands and talking. For a first course, we have lots of kissing and groping each other. For a main course, you have four choices: extra helpings of kissing and talking, a dish of hand motions designed as payback for that delightful mini-orgy this afternoon, or tongue braising, which is served with my head between your legs. We also have rock-in hen today, an intercourse served however you want it. The dessert tray comes later. And your order, ma’am?”

Mila started giggling half way through and had her head on my chest laughing by the end. It was pretty corny but it seemed to do the trick and bring her back to us.

“Skip the appetizer, please, I’ve had lots of nibbling today. Let’s go back to the first course. Then, can I have…I’m not really sure, but the last dish sounds a little heavy for right now. Can you describe the other two?,” she asked, pretending to appraise the specials.

“Of course. The hand entree starts with me slowly taking off your shorts and slipping my fingers in your underwear, where I gently touch the outside of your pussy and work my way up through your pubic hair, ultimately ending in a nice rhythm circling your clitoris. The oral is my personal favorite. We begin with some of the former and then I start to kiss my way all around your stomach and taut, gorgeous thighs. I spend as long as you will let me on that perfect ass, licking and kissing everywhere while I run my hand under your front side and begin stroking your clit. Then I lick up and down your cunt, moving into whole mouth adventures up and down each side. Ultimately, after other such events, I will suck your upper pussy while I roll my tongue around your clit. If you want it, the cook can push a finger in your cunt and put on some gentle, upward pressure. The oral sex dish focuses on your movements until I feel you cum while I’m sucking you. I think all of our customers would love this dish, but as you are the only one in the restaurant now and hopefully for awhile, I guess that’s just speculation.”

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