Crossdresser Evolution Ch. 06

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing

I was becoming addicted to masturbating while wearing panties. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's panties.

Recap - Crossdresser Evolution - Ch 02 - Getting my wife involved

I learn about feminized men and how some suck cocks. Then I taste my cum for the first time.

Recap - Crossdresser Evolution - Ch 03 - Getting Bolder and My Wife Finds Out

Wearing her panties to work. Getting caught when I get home. Then "The Talk".

Recap - Crossdresser Evolution - Ch 4 - Wife helps me buy my own panties and

I cum in panties in front of the sales lady.

Recap - Crossdresser Evolution - Ch 5 - Wearing Panties in Yoga Class

Wearing panties under my shorts in yoga leads to flirting and friendship with 4 students and the instructor.

Part 6 - Things Heat up with the Yoga Ladies

Meet-up with the ladies

We had decided to meet at Jane's house. I dressed in some loose fitting shorts and a t-shirt but wore matching pink lace bra and panties underneath. They were very see through and the panties were a string bikini style. The bra had wide lace straps. If you looked closely you could see the bra through my t-shirt. When Sue and I got there everyone except Elsa was already there. They each greeted us with hugs. All 4 of them hugged me with one hand under or on my shorts. My dick was slightly aroused before I walked in. Now it was fully hard only being restrained by my panties. Then Elsa walked in and she hugged me but managed to somehow get her hand under my shorts and caressed my already hard dick, saying, "Someone is excited about our get together." I just hugged her back.

We all went out to Jane's back patio. She had a very private backyard and it was really nice out. The 7 of us sat around her large glass top table. I was on the end with Sue and Elsa on either side of me. Jane brought out a couple of bottles of wine. I opened one, she opened the other and we poured glasses all around. Then we all chit chatted about nothing for a bit.

Then I felt Elsa's hand on my thigh. Remember the tabletop is glass. She slid her hand about halfway up my thigh and was just massaging it gently. My dick was again getting hard fast, which was probably her desired affect on me. After a couple of minutes she slid her hand just under my shorts, her fingers were almost to my panties and she continued to massage. No one had noticed anything to this point but I was getting more and more distracted but not wanting her to stop. I knew if she moved any more she would be on my hard panty covered dick. Then she moved in and laid her open hand on my dick. I gasped slightly and all eyes turned to me and then through the table. Sue said to Elsa, "I see you are helping my husband get in the mood to show us his panties. They will look much better if his dick is hard."

With that Sue stood up and pull me and my chair back from the table and said, "Let me help you with that," grabbed my shirt, pulled it over my head and off it went. There I was outside on Jane's back patio in a pink women's bra and shorts in front of 6 women, all quite attractive. They all started chanting, drop the shorts, drop the shorts... Sue took my hand to encourage me to stand. Once standing she undid my shorts, dropped them to the ground and I stepped out of them. Now I was standing there in my matching pink lace bra and string bikini panties in front of 6 women, AND my dick was hard as a rock.

Sue started to gently massage my dick through the panties until my precum started to make a wet spot. Then she just used her index finger to keep me mesmerized. Elsa stood up and started to massage my chest through my bra and after a minute or 2 moved in while my eyes we closed and started kissing me. We both got very passionate with our tongues exploring each other's mouths. She was very insistent on me sucking on her tongue. She was hugging me and wrapping one leg around my body, giving me a whole body hug. Sue started to remove Elsa's shirt so we were bra to bra and then removed her pants so we were also panty-to-panty. I couldn't believe what Sue was doing but I liked it.

I got free from kissing Elsa's mouth and started kissing down her neck and undid her bra and removed it. I loved kissing and sucking those beautiful breasts. They weren't more than an A cup, maybe a B but we're perfect to me.

I started to kneel in front of her kissing her belly on the way down. When I got to her panties I caressed her buns while kissing all around her belly button. Then I slide my fingers under her panty waistband started to slide her panties down.

THEN I saw it!! She had the largest clit I have ever seen. It was nearly 2 inches and it was VERY much on display with her hairless pussy. I heard a couple of audible wows as I started to run my tongue over it and wrapped my mouth around it. It was almost like sucking on the dildo but was warm and filled with life. Elsa let at a sigh of ecstasy and she just about melted to the floor. Everyone helped her down to the carpet as I followed with my mouth still working on her clit.

In a matter of a few minutes Elsa was arching her back and trembling as she came. I eased back on my stimulation of her clit as she climaxed. Eventually I slid up and gave her a a long sensual kiss before I slid off and stood up. All the others gathered around me and hugged me saying how wonderful that was to watch and how it was obvious that I loved doing it. I was quite worn out and went into the kitchen for some water. It was only then that I noticed that I had cum in my panties as well. That must have been why they knew I loved sucking on Elsa's clit.

I went to the bathroom, cleaned up, changed into a yellow bra and panties and went back outside. Elsa had recovered and was sitting at the table in her bra and panties along with all the others. I retook my place at the head of the table with all of use wearing only bras and panties. As I sat down I could feel myself getting aroused again from this unbelievable scene. I just grabbed my glass, refilled it and settled back.

Again, we were just chit chatting about nothing until things got back to what happened between Elsa and me. They all thought it was so exciting and sexy. They said I looked so sexy in my bra and panties, especially while giving so much pleasure to Elsa.

Sue then pointed out how excited I had gotten, " That was great when Mark came in his panties with no external stimulation. We play and he cums so easily when he is wearing panties. With very little stimulation I've been making him cum in his panties after he wears panties in your yoga classes. Other times he cums so easily when hearing about men being encouraged to suck dicks. I started having him suck on a dildo while I read the stories to him."

The ladies were very intrigued by all this. I was mostly embarrassed but when they all stayed interested and didn't seem to be judgmental I relaxed.

Then Elsa asked, "Can you and Mark demonstrate how you read to him until he cums or does Mark need the dildo in order for him to cum in his panties?"

Sue said, "Sure! We can demonstrate and the dildo is optional. He'll cum with the right story" She said all this without even glancing my way. Guess I don't have a say in this. In my head I'm thinking, how will this work? When home it is just the two of us with no distraction. Here I will have 6 beautiful ladies around me wearing only their bra and panties. This could be good.

We went inside and Jane got her laptop and projected it onto the TV. We all sat around the room on the couches and carpet. Sue told Jane, "I'd suggest that you get a towel for Mark to sit on to protect your couch from the inevitable outcome of him hearing about men sucking dicks."

After we were all situated Sue looked for some captioned pictures of men being encouraged to wear panties by their wives or girlfriends. I looked around and everyone was very interested and Sue read some of them out loud. I was hard in my panties and was creating a small wet spot of precum in minutes.

Then Sue looked for women encouraging men to suck another guy's dick. Now I was focusing more on the tv than the ladies around me. My panties were also getting wetter by the minute. Then Sue pulled out the dildo she had hidden in her bag and handed it to me. I looked around and they were all watching with big smiles on their faces. I reluctantly took the dildo and Sue moved my hand with the dildo in it toward my mouth. I opened my mouth and started to suck on the dildo as Sue went back to reading the captions. When she got into some more lengthy setups and descriptions I lost myself in sucking and fantasizing about sucking a real dick.

Off and on through all this Sue had been lightly rubbing my dick through the wet spot on my panties. She had stopped but the stories and descriptions had me in another world sucking on dicks. She got to a particularly descriptive one that described how the guy was working the dickhead with his mouth and tongue. I started to work the dildo just like he was and when the dick started to pulsate in his mouth the description put me right there with his fantasy cum pumping into my mouth. I came in my panties on the third pump. Sue scooped up my cum and I sucked it off her fingers.

Then I looked around and all the ladies had their hands in their panties masturbating. One was finishing up, two where in the middle of their orgasms and the others were in the afterglow of their orgasms. Sue was the only one that was preoccupied with the keyboard and reading to us.

I just thought to myself, how many people could say that they helped 5 women at one time achieve orgasms? This is amazing!! Sue looked at me and said, "You owe me an orgasm. I will be collecting when we get home."

When we got home Sue practically jumped me. She pulled off my shirt just inside the door and was grabbing my ass on the way up the stairs, finally pulling my pants down to my ankles at the top after I untied them. I stepped out of them, turned and we embraced in a passionate kiss. She had her hands all up and down my back and settled with handfuls of my butt cheeks covered with white lace panties that Elsa had loaned me. We sidestepped to the bed and fell onto it.

She slipped her shorts and panties off, sat on top of me as she removed her shirt and bra. In seconds she pulled my panties aside and slipped my already hard dick up into her wet pussy. I was in heaven as she worked my dick. I came in about 3 minutes.

Then she got off my dick and planted her cum dripping pussy on my mouth. In the frenzy, I just dug in, gobbling down my own cum mixed with her juices and moved to her clit. I had her writhing on top of me with a huge orgasm in less than 5 minutes. After her orgasm subsided she rolled off and we just laid there and fell asleep. We must have been a sight, me in Elsa's bra and panties with my dick hanging out and Sue naked and beautiful.

As I laid in the bed waking up the next morning I started recollecting how far I had gone from the first days of just feeling the softness of Sue's panties to today with me wearing a bra and panties while entertaining and helping 6 beautiful women in one night achieve orgasms. To boot, Sue, my wife knew, helped and participated in it all!!

Where the heck could this be going next? Can I please all 6 women? Then I thought, hell, what a way to die.

Yoga after that was so much more fun. The ladies were all very flirtatious and I knew they were getting as aroused as I was in yoga. Me showing off my panties and them watching for a glimpse of them.

The day after yoga each week became our meetup day. It always got to the point where I brought one of them to an oral orgasm while I was wearing a bra and panties and then me sucking on a dildo and coming in my panties while Sue read stories of cross dressing men sucking dicks. The tradition became, whoever I did orally brought the dildo. Of course when I got back to doing Elsa orally hers was a 10" black one. I almost was able to deep-throat it as they cheered me on.

The next week went a little differently. After yoga was done, the 5 ladies and I were talking when Elsa suggested, "How about we do a little more yoga, just the 5 of us?" We all agreed and Elsa said, "How about if we do it in our underwear and how about if Mark invites Sue to come down and join us?"

We each looked around and said that would be ok except Ann. She was blushing and said, "What if you aren't wearing any underwear?"

Elsa said, "We've all seen you naked at our get togethers, how about you do it in the nude?"

She hesitated and said, "I would feel too self conscious."

Fran chimed in and said, "I will be topless since my shirt has a built in bra," but Ann still was hesitant.

Elsa finally said, "How about we all just get naked!" Everyone finally agreed and we stripped down.

Sue was there in record time and we were ready to go in no time. We made a circle so we could all see each other while we did the poses. We started with some basic poses but started doing more poses that spread our legs apart. I loved those because I got to see their pussies all open. I could have sworn that many of them were wet and ready to be penetrated.

Then Elsa asked me, "Would you be willing to help with a new pose?

I said, "Sure," and stepped to the center with her.

She said, "You will be doing this one at a time let's start with you, Ann."

We stepped over in front of Ann and Elsa told her, "Ann do a shoulder stand while doing the splits with her legs."

I pictured her wide open pussy right there in front of me and my dick was sticking straight out in what seemed like seconds. Elsa helped her up and helped her slowly spread her legs. Then she motioned for me to take over.

Ann's pussy was right there, open, moist and ready for me to bury my face in it.

Elsa didn't disappoint me. She said, "Go ahead and see if you can give Ann a reason to hold that position."

I wasted no time, leaned in and did my best to bring Ann to orgasm. I was almost there and Elsa said, "That's enough, now it is Fran's turn."

We repeated this with each of them and Elsa stopped me just as I was about to bring each of them to orgasm.

I looked around and each of them was sitting cross legged and had a hand in their pussy. Elsa then asked me, "Now you get down and do the shoulder stand."

I got down and when I got into the position Elsa started sucking my dick. Unfortunately she did the same thing to me. I was just about to fill her mouth with my cum when she stopped.

There was a LOT of sexual tension in the room. I thought, yoga is supposed to be relaxing. This doesn't seem right. Will she help us to relax?

Well, she had a plan. She had us come closer to the middle and motioned me to come to the center. I did and as the ladies sat around me she said, "Do a shoulder stand." I did. I was looking up at my feet about straight up and my dick was sticking straight out.

Then she said, "Move slowly into a plow position and see if you can touch your toes to the floor behind your head."

I slowly lowered down but my toes were still off the floor but my dick was 6 to 8 inches from my face. She said, "Just relax into the position," as she wrapped her soft slender fingers around my dick and began to slowly slide up and down my dick.

She kept encouraging me to relax my back and my dick was now no more than 5 inches from my face. Then she said, "Let your legs bend a little so you can lower them a bit more."

With her continued encouragement I was able to lower until my dick was no more than 3 inches from my face. She was still sliding her hand up and down my dick and I wasn't far from shooting my load on my own face.

I felt like I really wanted to get my dick in my mouth instead of wasting my cum on my face. I opened my mouth and lifted my head. I was a little less than 3 inches from my dick when I let go. Elsa helped me to aim my dick into my mouth as I shot my load. It was very different having my cum go so directly into my mouth. I felt the warmth of it on my tongue as it pooled waiting for me to swallow it. My dick stopped ejaculating and I swallowed my cum.

During all this, I was more or less in my own world but as I came back to reality I noticed that all the women seemed to have masturbated them selves to orgasm.

I wasn't sure how she was going to do it but Elsa had help us all to relax. We all laid on our backs for a few minutes as Elsa talked us through some further relaxation.

Afterwards, Elsa pulled Sue and me aside and said, "I think Mark could suck his own dick with some stretching over several weeks. I'll send you some stretches that should help."

Sue said, "Great, it might be fun."

Elsa said, "Tonight was sure fun for me, and it seems all of us."

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We took a break from our weekly meetup for a few weeks but I did all the stretches twice a day and went to yoga each week. I did my stretches mostly without Sue but when we did it together she masturbated me into my mouth. After about 3 weeks I could just touch my dick with my tongue. Sue said she saw a precum string stay connected to my tongue as I reached for my dick and relaxed. I was so excited I blew my load almost immediately and missed my mouth with most of it. What a mess.

A couple of weeks after the first after-hours Yoga Elsa suggested we do that again. I called Sue again and we all stripped down again. We started in a circle again and after some warmup Elsa asked, "Jane and Mark, are you game to try a paired strength building pose?" We agreed and Elsa asked me, "Lay on your back and extend your arms straight up." Then she asked Jane, "Stand between Mark's legs and put both of you put your hands palm to palm with your arms extended as well. Now move your feet back near Mark's."

We were now face to face with outstretched arms with her directly over me. Now she told Jane, "Start bending your arms to lower yourself down towards Mark."

Then she asked me, "Mark, start bending your arms to lower Jane even closer. Now work together to see how close you can get to each other."

We both kept bending our arms until I felt her pussy touch my hard dick. We both paused and Elsa kept encouraging us to go further. I felt a little pressure on my dick and Jane shifted just a little. Then my dickhead slid inside her. Jane let out a little moan and we continued slowly moving closer as my dick push into her a little at a time. Then Jane's arms gave out, she came down on me and my dick slid all the way in.

My arms instinctively wrapped around her and pulled her close. I could feel that my dick was pushing on her cervix. We relaxed a little and Jane started to move her hips up and down on my dick. She pushed up to a sitting position and was riding up and down my dick, clamping onto my dick every time she came down. I lasted only a few minutes and filled her with my cum. After I finished she moved up and presented her pussy for me to bring her to orgasm. I did just like I do with Sue and slurped up all of our combined juices and then brought her to orgasm.

Again the others were circled around finishing up their masturbation. I looked over at Sue to see what kind of reaction there might be with me actually having intercourse with another woman. She just smiled. OMG she seems ok with this. On the way home Sue said, "That was exciting to watch. I came just after Jane buried your dick in her pussy as she came down on you."

Elsa contacted us all ahead of the next regular yoga class and checked to see it we wanted to stay late for some extra yoga and said make sure you bring a bra and panties. I just thought this would be some more fun and couldn't wait to see if I would get to fuck one of the others.