Mark (a cross dresser) and Steve (a straight divorcée) have a second meetup. Where is this going?

Saturday, the next day after Mary and Steve met at the bar and later hung out at Steve's apartment both of them were thinking they wanted to get back together. Mark/Mary was still a bit nervous that Steve still didn't know he was a crossdressed guy. Things could still go in a very bad direction if Steve didn't handle things well when he found out he had been making out with another guy.

 

Steve couldn’t get Mary out of his thoughts. He was thinking about how wonderful it was to feel a great connection with someone again. He both missed his ex-wife and was thinking about Mary. He still loved his ex-wife but she had wanted out. She felt like they had drifted apart and wasn’t willing to work on any kind of repair. Steve had been concerned that he wouldn’t ever find anyone that could measure up to how much he loved her. When Steve met Mary and had an almost instant connection he started to think maybe he had options and could find another companion.

 

Mark was already thinking about their next encounter and what the heck would he wear/ What the heck, was he thinking like a woman or what? He finally settled on his denim skirt and a sports top that he liked. He thought, "I think I need to tone down the femininity just a bit and be myself. I feel comfortable in the skirt and top. Both still are feminine but without stockings my legs might look just a bit less feminine so it will start giving Steve a hint when my legs aren't covered with silky material."

 

Steve was already thinking about where he might ask Mary to go or where to meet up. He thought, "How about just for coffee and meet at the Starbucks around the corner? Or we could go to the park and walk and talk on Sunday afternoon. The weather is getting to be nice and it would be a good place to just talk. We could go out to lunch but that seems to restrictive and I want to really get to know Mary better. Lunch might be too short. I think I should ask her to take a walk in the park after we stop at Starbucks for something to drink. We can also get something small to eat and share while we are walking. There are some nice places to sit down by the lake. Ok it's settled, now all I have to do is ask her, I hope she still wants to get to know me more..."

 

Steve set out thinking how to ask Mary out and settled on just a simple text. Steve wrote, "Mary, I really enjoyed last night with you and would like to get to know you better. How would you like to meet at Starbucks on Sunday about 3:00? We can have a cup of coffee or something and if you are OK with it, we can take a walk in the park. Let me know what you think." Steve read it several times and just hit the send button.

 

Mark was in the midst of thinking about what he would wear if Steve and he were to get together again when the text came in. Mark saw it was from Steve and opened it immediately and read it. Mark thought, "WOW, nice, we both seem to be on the same page except for him knowing that I'm a guy. Maybe I can figure out a way to let him know tomorrow. I hope he doesn't flip out."

 

Mark sent a text back to Steve, "Steve, I too enjoyed last night and felt a nice connection between us. I would like very much to meet you at Starbucks tomorrow."

 

Steve texted back, "Great, I'll see you tomorrow."

 

Mark spent the rest of the day thinking about how to tell Steve he was a crossdressed guy but nothing seemed to be the exact right fit so Mark just tried on different clothes to be sure he had chosen the right outfit. His panties were quite wet with precum both from trying on the outfits and thinking about how much he seemed to like Steve.

 

Steve gathered up a blanket in case they needed it to sit on in the park and sat around trying to watch TV.

 

Sunday morning came and Mark switched into high gear to get ready. Mary was ready by noon, way ahead, considering it was a few minute walk to Starbucks. Mary just sat on the couch and waited anxiously for the time to pass while playing on her phone. Finally she just said to herself, "I'm just going to head down a little early, maybe just people watch from one of the Starbucks tables out front until Steve shows." Mary headed out. When she hit the street she realized, "OMG, this is my first time out dressed AND in the daylight. Oh well, here goes nothing," as Mary headed down the street towards Starbucks.

 

Steve woke up early and couldn't go back to sleep so he headed out for a walk hoping to take his mind off how anxious he was about meeting up with Mary again, hoping that things would go well. It didn't really work so he headed home, showered and headed to the Starbucks a little early so Mary wouldn't have to wait for him even if she was a few minutes early.

 

Mary got to the Starbucks first and was checking out which table to take. She decided on one back against the building instead of any of the ones that were right up close to the pedestrians walking by. Before she got to the table Steve walked up and said, "Hi Mary, looks like both of us are a bit early, What would you like to drink? I can get it while you hold the table."

 

Mary visibly startled a bit, not expecting him that early said, "Wow, yes we are both a bit early, how about a vanilla latte?"

 

Steve said, "Funny, that is what I like too, guess I'll just get 2"

 

Steve went in and got the drinks and got a couple of pieces of their pumpkin bread for the park. Steve brought them back to the table and when he got there he said, "Mary, you look nice. I like that skirt and top together and they will be perfect for our walk in the park. I brought a blanket in case we wanted to sit for a bit."

 

Steve couldn't help but think that he hoped they might be able to use the blanket because he very likely would get a glimpse of Mary's panties if she had to sit on a blanket in that skirt.

 

Mary said, "Thanks, I really like this outfit too, it's VERY comfortable." Meanwhile Mary is thinking, "OMG, I may have to figure out out to sit on a blanket without totally showing Steve my junk hidden in my panties."

 

They talked for a few minutes, sipping on their coffees. Steve's mind kept veering off to Mary's panties under her skirt. Finally Steve just said, "How about we take all this to the park. It's much nicer there?"

 

Mary said, "OK," and they headed over to the park.

 

On the walk over to and into the park Mary kept noticing that she thought guys were looking at her. She thought, "Was it that they noticed she was a crossdresser or was it that they thought she was good looking or what?"

 

Steve spotted a grassy area off to the side a bit and in the shade. He said, "How about we spread the blanket over there? It looks really nice in the shade."

 

Mary said, "Sure," as they headed over and both of them refolded the blanket to a small square and laid it down. Mary sat down with her legs together and to the side a bit. So far her panties seemed to be hidden. Mark sat and they continued to talk.

 

Mary's legs were cramping a bit after a few minutes so she tried to shift a bit. She ended with one leg stretched out a bit and her panties were still hidden. Finally Mary just said, "Steve, I'm trying to sit ladylike here but its hard. I'm not much of a lady when it comes to this so I hope its OK if I just sit Indian-like."

 

Steve said, "Hey, we can go over to a bench somewhere or you can sit however you like here."

 

Mary shifted and sat Indian-like and held the front of the skirt down to cover her panties. Steve did however get a glimpse of her pink panties as she shifted.

 

As they continued to talk Mary would sometimes not be attentive to her skirt and Steve got more glimpses of her panties.

 

Mary was still looking for an opening to tell Steve he was a guy but didn't see any good openings. Steve asked, "Mary, would it be more comfortable if you laid down? Might be nice to look up into the trees and I could rub your feet and legs."

 

Mary said, "Sure, that would be really nice?" Mary slipped off her sandals, laid on her back and Steve moved below her feet and began to massage her feet. As Steve moved up Mary's calves and Mary's legs parted slightly Steve got a view of Mary's panties. At first he was just mesmerized by the sight of the material and continued to massage her legs and feet. Then he was unsure if he was seeing an unusual amount of bulge in her panties for a woman but couldn't see clearly enough.

 

Steve had parts within him that were wrestling with whether the mere thought of a dick in her panties was turning him on and another part that said he needed to find out to see if he needed to get out of this situation. Before he came to resolution in his head, Mary sat up and said, "I really appreciate you massaging my feet and legs but I really need to tell you something."

 

Almost before Mary got out the last word Steve leaned in and kissed her on the mouth. It turned into a very passionate kiss and they both laid down beside each other and continued to kiss passionately. Steve had his arms around Mary and was caressing her buns as he kissed her. Mary was just holding on in a passionate hug while she returned the passionate kiss.

 

After a few minutes of that Mary could feel Steve's dick hardening in his shorts against her body. Meanwhile Mary's dick was also hardening but she was purposely keeping it from pressing into Steve.

 

After a few more minutes, both of them broke off the kiss and laid back on their backs. Steve said, "I don't know what is coming over me but I feel this great connection with you and don't want it to stop."

 

Mary had forgotten that she was about to tell Steve she was a crossdressed guy and just laid there and then said, "I'm feeling some of the same thing."

 

Steve got back up, readjusted his shorts as his hard-on started to subside. He resumed his position massaging Mary's feet and calves. This time he started to go up over Mary's knees to her thighs a bit. Both of them were in heaven but Mary's dick had not shrunk back completely so Steve was seeing a bit more of a bulge in her panties than before. His dick began to grow again as he wondered if Mary had a dick and that was what she felt she needed to tell him.

 

Steve thought, "What would I do if Mary did have a dick? I am still feeling a wonderful connection to her. Does it matter? I'm not gay but I do want a connection like I am feeling. Man, now I have to know. Do I just ask or do I just continue? Asking would be awkward. What if I just discover it and accept Mary as she is if she has a dick? I think I am just going to continue with this massage and see where things go."

 

Mary is just laying there enjoying the massage now and her dick is staying in a partially hard state. She says to herself, "I know my dick is partially hard, showing more in my panties and I am probably also leaking precum into my panties but this feels so good I just don't care if Steve sees, in fact I hope he does but accepts me as I am."

 

Steve continues the massage and moves up Mary's thighs more and more. His dick is now hard and you can actually see his dick head sticking slightly out of his boxers and short's leg hole. When his hand lightly brushes against Mary's dick in her panties the world stops for both of them. Steve's hand is still touching Mary's dick when suddenly Mary's dick twitches against Steve's hand. That is when Steve rolls up over Mary and starts to kiss her passionately while lying on top of her. Steve's dick is now pressing firmly agains Mary's dick. Both dicks are twitching and pushing against each other as they kiss and they push their hips into each other.

 

They continue to kiss and grind together until Mary starts to near orgasm. She clutches Steve tightly and she feels her dick pumping cum into her panties. After a couple of pumps of cum into her panties Steve, feeling her dick ejaculating, has an orgasm and pumps his cum out but cums all over the outside of Mary's skirt creating an enormous wet spot and soaking into some of the hem of Steve's shorts. Both of them are so busy enjoying their respective orgasms that they don't realize what is happening as they stay in their loving embrace.

 

After a few minutes Mary feels Steve's cum soaking through her skirt and panics a little. Steve rolls off and the mess is revealed. Both Steve and Mary exclaim at the same time, "Oh SHIT." It was a good thing that they were pretty far from the path where people periodically walked by. Steve grabbed the bag with the pumpkin bread and pulls out the small pile of napkins he had put in there and both Steve and Mary try to clean his cum off the front of Mary's skirt but denim shows wet spots, big time. They grabbed the edge of the blanket and continue to dry her skirt as much as they can. So far they hadn't done anything with Steve's shorts but the skirt was the bigger mess.

 

Mary finally said, "Hey, let's just sit here and talk a bit longer. The sun will start to head down in not too long and then we can make our way back in the lower light and the denim will be a little lighter as it drys a bit more. Besides, I think we have a bit more to talk about after that."

 

Steve says, chuckling, "Yes I guess we do but before we go too far I'd like to say that was extremely fun and one of the best orgasms of the century."

 

Mary said, "Yes, it was amazingly good for me too. I've never cum like that before, from just grinding together. Well, Steve, now you know what I was trying to tell you the other day. I'm a guy that likes to crossdress. Until the other day in the bar I had never ventured out dressed, only hung around the house. After getting the dress I wore that first night I decided to buy a wig and some makeup. I seemed to look pretty good and wanted to venture out and see how it went. I had no idea or plan to meet up or do anything with anyone while I was out. Then I met you and we hit it off so well with me as Mary. You stirred things in me that I didn't know were there and I didn't want it to end but felt I needed to tell you I was crossdressed. I was afraid it would go badly and I would never see you again."

 

Steve said, "I was actually at that bar trying to meet women for the first time in over 20 years. I was so nervous. It was fate that we both ended up there at the same time and you ended up sitting next to me. You also stirred several things in me. I wasn't sure I would ever have such a connection to another woman that I had with my ex-wife. It was exciting to me that we hit it off so well. Then when my hand brushed up against your panties and I felt your dick inside the world stopped for me. When your dick responded to my touch I felt this overwhelming passion toward you. I never thought another dick would turn me on like that."

 

Mary said, "WOW, who would have thought... how about we head back now? I think the sun is down enough. How about we head to your place since it is closer. There I can clean up a little more before heading home."

 

Fortunately, the walk was uneventful. It seemed like one couple might have noticed the dampness of the skirt but they didn't do anything. When Steve and Mary got to Steve's place Mary slipped off her skirt and Steve gave her a damp towel to clean it a little more. Mary was standing there in only her top and panties and the panties were still quite wet from Mary cumming in them. Cleaning the skirt was pretty pointless and Mary said, "This isn't doing much, I think it will be dark enough that no one will notice anything."

 

Steve said, "I'll also walk you home to be sure nothing happens to you." Then Steve stepped behind Mary and felt and massaged her buns through her panties. Mary turned and they kissed again with Steve pulling Mary close by holding her buns.

 

Mary said, "Steve, I feel like I want to see your cock. Can I take your shorts off for you so I can see your cock?"

 

Steve said, "Are you sure? There are no expectations of anything."

 

Mary said, "I know but I have this intense curiosity building inside me." with that she undid his belt, button and unzipped his shorts. Then she grabbed both his boxers and his short and lowered then slowly down until his partially hard cock was visible. She said, "Wow, you have a nice cock!" as she lowered his shorts to the floor, kneeling so he could step out of them. She was now eye-to-eye with her first cock.

 

Mary said, "This is beautiful. Can I touch it?"

 

Steve said, "Yes, you can do anything you want but again there are no expectations."

 

Mary wrapped both hands around his cock and it jumped with her touch as it hardened more and more in her hands. She stroked back and forth gently and felt the firmness building within his cock. A little precum started to ooze from his cock and Mary started to feel the urge to suck Steve's cock. She leaned in and without another word slide his cock into her mouth. Steve moaned with pleasure which fueled Mary's desire to suck even more. She moved her head back and forth taking more and more of his cock into her mouth until he was gently hitting the back of her throat with each stroke. Steve was just moaning with pleasure the whole time. Soon Steve was nearing orgasm and started to tense up to release his load. Mary just intensified her sucking and felt her passion building even more. Steve's cock twitched a bit in her mouth and then jettisoned his load into Mary's mouth. Mary simultaneously came in her panties and swallowed pulse after pulse of Steve's cum as his cock pulsated in her mouth.

 

Mary laid back on the carpet totally wiped from the intensity of her first time sucking a cock. It was so passionate and she was in the heavenly afterglow of her orgasm and the memory of feeling Steve's cock pulsing to deliver its luscious load into her mouth.

 

Steve almost collapsed next to her on the floor with his dick still slightly erect but softening. They rolled towards each other, hugged and kissed tenderly for a few minutes and then just laid there in each other's arms.

 

After what seemed like an eternity, Mary said, "Steve, unfortunately I really need to head home, I have to get up for work early tomorrow but I really want to see you again soon. Can we have dinner in a couple of days, say Wednesday night?"

 

Mark said, "Sure, I'd like that."

 

They both got dressed and Steve walked Mary home. It was quite dark now so the only risk was when they entered Mary's building. They saw one other person but Steve kind of walked in front of Mary to block their view of Mary's cum stained skirt.

 

When they got to Mary's door Steve said, "I am looking forward to Wednesday night. I'll figure out some options for where to eat unless you have something in mind."

 

Mary said, "You pick it. It's kind of nice playing the stereotypical woman's role for a change."

 

Steve just leaned in and kissed her goodnight and said, "I like treating you like a lady. I'll see you Wednesday night. I'll come by about 7:00 if that is OK with you."

 

Mary said, "Yup, fine with me."

 

Steve walked home with a new spring in his step. This was a wild couple of days but he was feeling better than he had in quite some time.

 

That night both of them went to bed thinking about each other and where the heck was this crazy relationship thing going?

 

 

 

Done