Matchmaker Make a Match

Cassie Longstreet, my 26 year old sister, lives with her partner of two years Katie Kenwood in a 4th floor apartment overlooking Washington Square park in Greenwich Village.

Five years out of the closet, her revelation had come as a huge surprise to the family. How does a girl who was popular with boys and who dated her fair share of them turn out to be lesbian? As I recall, it took our parents a long time to come to terms with Cassie's sexual orientation.

I did benefit from having an older sister to pave the way for me. When I came out 6 months ago back in January my parents could accept my reality without reservation. Though coming out was not easy for me, it did not go badly.

Anyway, a Saturday afternoon finds me sitting at Cassie's and Katie's dining table sipping beer from a mug while engaged in girl talk. That day was to become a turning point in my life.

I knew Chelsea Preston but only superficially. Much of what I did know about her came through chit chat or the grapevine.

Cassie spoke freely for a couple of minutes.

"Stephanie you and Chelsea would be good for each other."

I asked, "what is she into."

"Softball," said my sister.

Hearing that brought me back in time. Though I hadn't played since college, I still can enjoy watching a game. Maybe she and I can enjoy a game together. There's room for two on my sofa.

My sister and her partner never struck me as matchmakers. In fact, the subject never even came up until that day.

Though out, I was not dating anyone nor could I see myself frequenting lesbian bars. The only thing I did know is that I'd rather take a chance with my heart than have one night with a girl whom I may never see again.

A half hour passed then my sister's phone rang.

"I'll be right down."

I looked at Katie who read my mind.

"She's not unattractive," said Katie.

Chelsea Preston came inside one step ahead of Cassie. She is 5 7 with modest breasts. Short blond hair touches the tops of her shoulders. She has full coral pink lips. She is wearing a Santorini blue tank top with tie dye blue pants and stacked block-healed booties

Chelsea and I immediately struck up a long winded conversation that seemed to exclude Cassie and Katie. It soon became clear to my sister and her partner that we hit it off.

Chels, it turns out, devotes a lot of time and energy to keeping herself fit. A long run through Washington Square Park has been her routine for years.

"Stephanie are you into running?"

"No but I rollerblade," I replied.

"I'll run and you can skate at my side."

I like that idea. I think this is the start of a beautiful friendship.

Washington Square Park is a rectangle, its long sides stretching north west. It's perimeter is an asphalt track. A circular common in its center is traversed by some narrow walkways. Several dog owners are there with their pets.

Chelsea had changed into black Nike running shorts and pink sports bra. Her legs are firm and muscled. Her boobs are bigger than I had previously imagined.

Minutes after 5 she started her run with me skating by her side. Her stride seemed easy. I skated at a leisurely pace keeping along side her.

She reminisced. "I've been running since high school days. I was on the track team."

I asked, "did you graduate with Cassie."

"Class of 2013," she said. "Your sister wanted to be my girlfriend."

"Really," I exclaimed. "She was straight back then."

"After high school," said Chelsea.

Probably when she first came out, I guess.

"She came out five years ago."

"Five years ago she asked me for a date."

That was all for that conversation.

"She talked about you but she never said that."

"I was in a relationship."

I asked, "with anyone I know."

"Do you know Karen McKinley?"

I shook my head in reply.

We kept exercising and kept up our chat. Legs began to tire out, at least hers did.

Chels turned toward the common where she stopped to rest and catch a second wind. I stopped along side her.

"I got into rollerblading two summers ago. Some girls were doing it and it looked like fun."

I sat to change into my running shoes then stood up and called for a ride. Seconds later my phone identified the UBER as a 2013 Toyota Prius plate number LINY151 driven by Matteo.

I said to Chelsea, "maybe he'll let us share a ride."

She asked, "are you going home."

"Uh huh," I replied.

"They won't let us both in at the same time." She called for her own ride.

My West Village apartment is on the third floor inside an old brick building. Chelsea is no doubt home by this time watching television.

A couple of days passed. Lenox Health x ray waiting room has never fewer than 5 patients so this girl has plenty to keep her busy at least from 6 a.m. to 2 p.m. Between patients Chelsea is on my mind but not the only thing there. Like me she also works in the medical profession but as a nurse at Mount Sinai Beth Israel.

Tuesday evening at 5 finds me just taking dinner from the oven when my phone rings. Caller ID indicates Chelsea Preston.

"I'm so very glad you called."

My unspoken message was that I wanted her to call because we should be girlfriends.

She asked, "what are you up to."

"Not a lot," I replied.

"I'm going shopping the Scotch & Soda. Are you up for it?"

"I'm just starting dinner and yes I'm up for it."

"Okay, about 45 minutes," she said.

Thoughts of Chelsea turned to lustful thoughts making me strip naked and plop into my sofa. My clit soon became engorged under the hard rub and the labia spread open exposing pink flesh. Muscles went into spasms causing me to quiver and moan softly with delight. Breathing is shallow. Heartbeat is racing. My vagina ballooned. Will I climax before she comes to the complex where I live? Bent on ejaculating, I kept my fingers busy.

Suddenly a powerful orgasm left me huffing. After taking a minute to recuperate I cleaned myself and dressed in clean panties, Wine Crochet cold-shoulder top and white jean shorts.

I had barely a minute to wait before Chelsea arrived and called from the sidewalk.

The clothing here is way too expensive. I hung the Hawaiian shirt back on its spot. We walked away at a slow pace toward the dresses.

I asked, "do you shop here often."

"I buy one garment a year here. I love to look."

The next few nights saw Chels and me chatting via Face time. Each chat lasted more than an hour. Saturday morning finds us sitting at my dining table having coffee and chatting. I am undressing her with my eyes.

She spoke freely turning mundane girl talk into something more private. "Steph where was the most unusual place you ever had sex?"

I hesitated prompting her to make a remark. "You're a Virgin, aren't you."

You got me there. "Do boys count?"

"Yah," said Chels.

I told my story. "I was 19. Me and this boy, a blue-eyed blond, rode out to the Hamptons. We did it on the beach under the moonlight."

"Kinky," quipped Chelsea.

"Excuse me," I said.

Minutes later I returned naked from the bathroom and sat close to the girl I want.

"Nice tits," she quipped pressing my nipples with her fingertips. We leaned into an open-mouthed kiss. MY tongue pushed against her tongue. Hers pushed back. She put her palms against my breasts pushing them upward.