Two Couples in Madison Pt. 01

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This is a fictional work.

The date had been on the calendar and circled for a long time. Sunday August 20, 2017. That was the date for the annual Gay Pride Walk in Madison Wisconsin. Actually it had been on many calendars and circled by many people wanting to profess their love and their sexuality.

Steph and Jenny lived in Madison, Jenny was a budget and financial analyst for the state legislature. Steph was a business analyst for Wisconsin Mutual Life and Casualty company.. They had been together for five years, five happy years of being soul-mates and lovers.

On the other hand, Emily and Karen Ryan were fairly new to the Pride Walk. Karen two years ago underwent a vaginoplasty, where her former penis had been changed to a vagina. It had been 8 years for Karen to fully make the transition from male to female.

Karen was a professor of economics at Wisconsin State University – Superior. She was well accepted in her department and on campus. Emily was an analyst for the Great Lakes Shipping Consortium


The organizers of the Madison Gay Pride walk had asked by social media for local people to open their doors (and beds) to those coming from around the state for the event. Steph and Jenny did post on the social media site that they were able to host a lesbian couple. Karen and Emily posted that they were interested in having a room for Saturday night.

On July 20th, a month before the event, Steph was checking the listings for those who had rooms and those who were looking for rooms.

She called out the Jenny “Hey, one of my old professors from the University of Wisconsin – Superior and her partner are coming. I loved having her as a professor. Could we host them for the Gay Walk?”

Jenny came out of the kitchen to look over Steph’s shoulder and said “Sure, invite them to come and stay with us.”

Steph went on to explain to Jenny “She was in the early stages of mtf transformation when I had her. I’m pretty sure she is done now.” Steph paused and added “Some of the students weren’t very nice to her. She was just learning how to do make-up, how to do a female voice, and how to walk in heels. I got to interact closely with her as my advisor. She knew I was a lesbian and she wanted to understand that.”

So, Steph started the interaction with a simple email to Karen and Emily “We’d love to have you stay at our place when you come for the Madison Gay Pride festival.”

Karen got the note when Karen and Emily were having a second cup of coffee and she remembered Steph fondly.

Karen said to Emily “A former student of mine, Steph Wilson and her partner have invited us to stay with them for the Madison Gay Pride March. I think it would be fun. What do you think?”

Emily agreed and Karen, at the kitchen table they sent a note back to Steph “Steph, what a great surprise to hear from you!! Yes, Emily and I would love to stay with us on Saturday August 19th and go to the Gay Pride March on Sunday with you. Could that work.”

Karen added a little postscript “And, how are you? I’d love to see you and update you on my progress. I had my vaginoplasty two years ago and now I really am a woman, in a loving relationship with a woman, life is SO good.”

When Steph got Karen and Emily’s response, her mood definitely took an upswing.


Karen and Steph exchanged a few more emails in the month leading up to the Madison Gay Pride event.

Karen and Emily were coming from Superior Wisconsin which was about 4.5 hours driving time north from Madison. Karen thought they could get to Madison about dinner time, would that be an acceptable time? Karen also volunteered to take Steph and Jenny out to eat and then maybe back to their place for visiting.


Ding Betturkey dong. Steph’s heart beat went up several beats. Karen and Emily were here.

Steph opened the door and while she did recognize her old professor immediately, there had been many positive changes. The hormone replacement treatment had worked wonders. Karen had real breasts now, (Steph was remembering some of the first days for Karen as she started her transition, where she wore breast forms). Her skin was soft, and, wow, she had hips, and … She was beautiful.

Immediately Karen and Steph hugged deeply with mutual comments like “It is so good to see you again”. Meanwhile Emily introduced herself to Jenny with a hug as well.

They had about 15 minutes to get to the restaurant where Steph had made reservations, so there wasn’t much time for small talk. Karen and Emily brought in their suitcases; and then jumped into the backseat of Jenny’s Toyota Prius. Steph noticed that Karen and Emily held hands and kissed in the backseat of the car.

The restaurant was very nice. The staff put the four of them in the back where they could talk.

Steph started out “Professor Ryan, you look awesome”.

Karen grinned and replied “That you Steph. That was what, six years ago. Please call me Karen. I think you were in class the first semester I went full-time female.”

Steph nodded and said “Yes, there were some of my classmates that weren’t very nice to you (at least behind your back).”

Karen smiled “Yes, I remember that. I remember a morning when I had trouble getting my dress buttoned up correctly. Emily was gone to her work, and I came to class looking like a disheveled professor (and was one). I was trying to use make-up, and become a woman.” Karen paused and laughed out loud “What a learning semester!!”.

Karen continued “Do you remember Professor Ammons? She was a lesbian in the accounting department, and she took me under her wing after that semester. I would stop by her office in the morning and she would adjust my clothes, comb my hair, and make sure I was presentable. But, like my students I learned and adjusted. A year ago, I got the Outstanding Faculty Award – the first and only faculty to win that award in two different sexes.”

The discussion continued as for how Steph and Jenny had met.

Jenny told it this way. “We were both new to Madison, and the Chamber of Commerce had a mixer for new professional employees in the community. I wasn’t going to go, but my boss insisted that go. There, across the room, I saw Steph, our eyes met, kind of a love at first sight. Our first date was two days after than and we’ve been together five years now. We got married three years ago for the various benefits, but mostly since we are real soul-mates and best friends (and lovers).”

Dinner conversation went back-and-forth freely. Karen was enjoying connecting with Steph and again and getting to know Jenny. All four of them were like old friends by the end of dinner.

As they left the restaurant, all four made sure they visited the restroom, seemingly they all wanted to empty their bladders before going home.

Karen noticed that Steph and Jenny had a long passionate kiss in the restroom. She smiled – love is around us she thought.

Back at Steph and Jenny’s place, the pace picked up. Walking in the door, like on cue, Steph and Karen immediate started to hug and kiss deeply and warmly. Emily and Jenny followed that cue as well. Out of the corner of her eye, Karen saw Jenny hold Emily’s hand and they went to Steph and Emily’s bedroom.

Karen and Steph went to the guest bedroom. Closing the door, the two locked lips in a passionate kiss. Karen Betturkey Giriş hadn’t know what to expect spending the night with Steph and Jenny; and probably Steph and Jenny hadn’t know what to expect with two middle age lesbians staying the night with them; one of which had been her professor. They kicked off their shoes.

Steph was certainly enjoying the kiss as was Karen. Soon Steph’s hand slipped down Karen’s torso, and stopped at Karen’s breast. Steph could feel Karen’s heartbeat through her blouse and bra. Karen’s hands also slid down Steph’s body under the arms along her side.

“I think we might need to get a little more comfortable” was Karen’s panted out suggestion. “Let me help you out of some of your things.”

Karen unzipped Steph’s dress and helped pull it over Steph’s head. She then took off Steph’s hose, so that Steph was only in matching Victoria Secret panties and bra.

Steph did the same, unbuttoning Karen’s blouse and taking off her dress slacks and hose. And Steph noticed that Karen was dressed in matching Soma panties and bra.

Steph whispered “It was almost like we were expecting to do this.”

Steph added “You can go first professor”.

Karen corrected her “just call me Karen”.

But Karen took her cue. “Lay down on the bed Steph, I think we have some time for some special foreplay.”

Karen started with Steph’s feet and nibbled and kissed her way up to the inside of Steph’s thighs. Steph was moaning with anticipation, as Karen moved to Steph’s belly and kissed and nuzzled around Steph’s belly button. Steph was arching her back in the glow of being aroused and excited.

Karen slowly started up from Steph’s belly below her bra and nibbled and kissed below the bra and above the bra. Reaching around the back, Karen unhooked Steph’s bra, and paused in rapt admiration.

Karen gazing at Steph’s breasts said “What beautiful breasts you have Steph”.

And, Karen started to kiss around the breasts, not touching the areolas and nipples.

Steph quietly commanded “Suck my breasts, Karen. They need to know your love and touch.”

Karen didn’t need more direction and started on the left breast, around the edge, but soon rubbing Steph’s nipple with her lips; and then pulling in the erect nipple into her mouth and gently nibbling and sucking on that beautiful projection.

Steph gasped and said “I’m cumming”. But, Karen wasn’t done, and went to the right breast and did the same. Karen slid her right hand inside Steph’s panties and found them soaked with Steph’s juices.

“You are wet” Karen said.

“Yes” was the simple response from Steph.

“Can I finish you before you start on me?” Karen asked.

“Yes” was the same response from Steph.

Karen rearranged herself positioning her mouth over the triangle where Steph’s legs intersected with her body. She then took off Steph’s remaining piece of clothing, her panties.

Trying not to get too close to the vagina area yet, Karen kissed and nuzzled her way around the outside of her vulva lips. The aroma was so exciting to Karen as well as the fact, that she was making love to a friend.

Karen was thinking and commented, “Steph, I’ve only had one partner in my entire life and that is Emily. I am so excited to be with you tonight”.

Then, Karen looked at Steph’s beautiful vulva area. Steph’s vulva colors were a deep purple gradually becoming a deep pink on the outer lips. Her outer lips were large, at least according to Karen’s very limited experience.

“So beautiful” thought Karen in an awesome way.

Taking her right index finger she carefully ran it around her outer lips in a clockwise direction. Steph’s body was pulsing as Karen took her finger away and replaced it with her tongue, just lightly licking Steph’s outer lips. Three times around, but then, Karen stopped at the top and backed her tongue out and brought her finger in again.

Yes, just a little under the upper joint of the outer lips, was Steph’s clitorius, already erect. Karen knew to be especially careful and thoughtful with that delicate sexual organ.

Karen took her index finger and spread Steph’s outer lips. Karen peered at the inner lips, wrinkled and very wet. She put the finger and then a second finger into Steph’s vagina and circled slowly. Then she brought her tongue in a gentle lick of Steph’s clitorius.

That was all it took. Steph cried out “I’m cumming”, and reachied a full and pulsating orgasm that Karen licked up with pleasure.

Although not a natural woman, Karen had been well tutored by Emily. Emily had always wanted to share Karen’s orgasms through deep kissing. Karen adjust her position to be face-to-face with Steph and they kissed deeply and shared the orgasmic fluids off of Karen’s tongue.

As their kiss subsided, Steph said to Karen, “My turn professor, umm, Karen”.

Steph’s foreplay antics were similar, work from outside to inside. From kissing Karen’s feet and working up the inside of her legs, and from kissing Karen’s arms and working to her stomach, Steph was building a volcano deep inside Karen that would erupt in the near future.

Steph took off Karen’s bra and panties. She paused to sniff the wet panties and even ran her tongue over the soaked fabric.

Steph commented quietly “What delicious panties that cover your beautiful pussy.”

Steph worked over both breasts, sucking the nipples until Karen thought maybe they would come out (and also helping Karen get an orgasm).

Then Steph went down her body to Karen’s pussy. Karen’s pussy was a more delicate pink and yellowy flesh color. And like Steph’s own pussy, Karen’s was fully wet from a previous orgasm and puffy in anticipation of more.

Steph did have slightly more experience in having sex with other women, although Jenny was her spouse and her love and lover. She brought Karen to the brink of orgasm twice. Steph put a finger just barely inside Karen’s anus. But, as soon as Steph put it in and sensed Karen was ripe and ready, she pulled it out again. Twice, she did that while lightly kissing Karen’s clitorius; and finally she sucked on Karen’s clitorius and brought her to full wet climax.

Steph loved eating pussy and did it frequently with Jenny. Karen was a new conquest for her and Steph was an expert in bringing Karen to a third and fourth climax.

Eventually, the two shared a deep, lovers kiss. Karen had a smile on her face that spoke volumes of happiness, contentment and satisfaction. They napped a little until they heard somebody in the hallway heading to the bathroom. They put on their bras and wet panties and went into the hallway. Emily was in the bathroom. Too much water at dinner Karen guessed.

All three of the four of them in the hallway with bras and panties. Jenny came into the hallway naked. Karen quickly noticed that Jenny had a landing strip on her pubic hair.

“Wow, don’t you look nice” said Karen.

Jenny didn’t blush. “I don’t think we told you that we go a nude camp every summer.”

Karen looked at Steph, who nodded “It really helps us determine what is important in our lives. No, there is not a lot of sex, other than at night between my best friend, Jenny, and myself – and we keep that behind closed doors. You two should try it”.

Emily looked distressed at Karen, who wasn’t quite sure about the idea either.

Karen spoke up “Well, at age 48 I imagine I’m missed a lot of things, including nude camping.”

Nodding to Emily “We’ll have to discuss that one”.

Exhausted after their romp, the four did go to bed and slept soundly until morning.

To be continued.

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