Autumn by Marina Ch. 03

Story Info
Autumn's first days on HRT & Marina gives her a sissygasm.
3k words
4.58
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Part 3 of the 7 part series

Updated 09/19/2023
Created 05/14/2020
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3.

Marina was set to travel for the next 4 weeks on business, so this was our last evening together. We were back at her place, getting dressed to go out to dinner and dancing.

I was having second thoughts about going out in public. "Are you sure this is a good idea?"

"Autumn, don't worry about it. You're going to look great and who cares? Anyone who does notice won't want to say anything offensive."

So with that reassurance, I put on the black mini-skirt Marina had set aside for me and the white sleeveless top. "If you went through all the trouble to remove your arm hair, may as well take advantage of it today." I had cream colored lace panties and a black padded bra.

I started my own makeup as Marina did hers adjacent to me, half watching me and giving me pointers. Finally, I put on my wig. Sheesh, I had started to think of all of this as "mine"! Before leaving, I made sure to have another dose of my medicine.

Dinner was good but uneventful. Dancing was at a gay bar. Marina introduced me to some friends, and Stephanie and Amy were there. We all danced with each other, including a couple other girls whose names I couldn't hear over the music. I received several compliments, and made sure to give as many as I got. We were ready to leave, but Marina and I had had too much to drink, so we went to Amy's house which was only a block away.

As soon as we were in the door Amy looked at Marina and Marina nodded. Amy moved in front of me and I backed into the wall and Amy kissed me passionately. "I can't wait to try out the new girl."

Marina moved in and gave Amy a kiss and then me as well. "Are you pimping me out?" I asked Marina, jokingly.

"Do you mind it?" She smirked.

"No!" I said as we all moved to Amy's bedroom. We all covered eachother in kisses as we took off each others clothes. Amy ended up laying on the bed, and Marina got in position to straddle her face, watching me dive into her pussy with my tongue. Marina was moaning with excitement as soon as Amy's lips touched Marina's lower lips. I could hear Amy moan occasionally as I licked her and rubbed her clit with my tongue.

We saw Marina shake in climax as her moans increased in pitch. She then got off Amy and licked her juices on Amy's face with kisses. Amy then ordered me into her pussy. "I want to feel your real strap-on creampie me," she said.

I was only too happy to do so, but felt I should confirm with Marina that she didn't mind. She nodded yes, and I could see she was very excited by the prospect as well. So I knelt between Amy's legs and leaned forward, entering her missionary style. Marina kissed us as I did so. In a few minutes, because I had eaten her out already, Amy was cumming and begging me to fill her. I started moaning as well, trying to sound like her and filled her with my juices.

I slipped myself out and Marina dove in with her tongue, licking our combined juices then sharing them with both of us through kisses.

We all fell asleep in Amy's bed naked.

--

We stirred the next morning, took a shower together that involved a lot of caressing, then got dressed and said our goodbyes. Marina and I went back to her place, but she had a lot to pack so we said goodbyes again and I left. She did say she would have challenges for me each day. She also expected me to follow a workout routine each day and to take my medicine.

She texted me from the airport after I worked out. My challenge for today was to change up part of my wardrobe. I was to lock away all my boy underwear and go to Amazon and buy another set of panties, a dress, two skirts, two women's tops, stockings, two more bras, a makeup kit, and women's deordorent. She gave me my likely sizes, and some of the clothes had some sizing guides. They were all set to arrive in two days. I showed her the order as we facetimed. She linked me a few videos of girls describing their first few months on HRT.

The next day was Monday, so I was back at work. I wore panties, but I was otherwise dressed normally. Marina ordered me to change clothes as soon as I got home, so I put the skirt and top I wore the prior day back on. I didn't have too many things to choose between. She verified that I was taking my pills, then linked a few more videos to watch about being transgender.

Tuesday I wore panties and normal clothes again to work. But before I got home she told me to go to a sporting goods store and buy a women's running shoe, so I could get my size. The sporting goods store doesn't have people helping you--you just size yourself, get the shoes and try them on, so I could get a women's pair without being too uncomfortable. When I got home my Amazon order had arrived, so I changed into a jean skirt and a red sleeveless shirt, with a padded bra underneath and my new women's sneakers. Marina facetimed me as I was checking myself out in the mirror.

"I love that you are looking yourself over. Feel any different?" She asked.

"Not really."

"Well, give it time... it has only been four days, and it will likely take some time. The first changes seem to be lower libido and softer skin."

"No and No," I replied to the implied question. "But now that I think about it, I have fallen in love with olives."

"Ah, ok, so something is happening... some pregnant women get cravings for them because of their hormone changes." I felt strangely reasssured.

"Now that your order arrived, make sure you spend 30 minutes each evening trying your makeup. I want you to be an expert by the time I'm back. You also need to think about your voice. Here is a series of videos on increasing you pitch. Try those and a voice pitch app for your phone."

"Yes maam." Between the workouts, makeup practice, and voice practice, there was a lot to keep me busy.

Wednesday was another day of panties and work clothes during the day. My first appointment with a therapist was at 11am, so I left the office a little before 11 and met Christine. Stephanie had given me her card a few days before that. Christine and I had a relaxing talk about many of the incidents I had mentioned briefly to Stephanie. She concluded by saying, "I'm glad you found Stephanie and she referred you to me. While you can get hormone perscriptions via something called 'informed consent' at some doctor's offices, surgeries, if you want to go down that path, usally require one or even two therapist's recommendations." We agreed to meet again the next week.

I went back to work, and when I got home in the evening I put on the dress (floral-print) and stockings in the evening, after my workout. Marina texted me after I did my makeup too and complimented my look. She found matching shoes online and told me to order them in my size. She also reminded me to put on a new Estrogen patch.

Thursday after work I worked out first. After a shower, I wore the new burgundy skater skirt I ordered with a white blouse. I practiced my makeup and my voice. When Marina facetimed, I tried my voice with her. She felt there was progress, but it still needed a lot of work. And I couldn't keep the pitch correct consistently. She also reminded me to shave my legs and armpits and anywhere else I didn't want it to grow back. Ideally that would be everywhere, but I couldn't justify the time, or reach some places. So I used the Nair cream in places as needed.

Friday she texted me that I should do my nails since I could keep them colored for the weekend. So after my workout and shower I did them as best I could, while watching some videos. I did my toenails red, but sort of chickened out on my fingernails and just went with a clear finish. When she facetimed, she asked to see them and was disappointed with my fingernails. "I wanted you to wear a red or a pink or purple, then you could take it off at the end of the weekend. But now... well, you are not allowed to take the finish off until Friday, and you must touch it up as well. She had to go out that night, but said we could have some fun Saturday night over facetime.

So I finished the night wearing just an old t-shirt and panties to bed as usual. But this time when my skin rubbed against the sheets I felt so soft! I had read this was one of the first signs of the hormones taking effect, so they were!

Saturday was a day to catch up on many errands because my evenings were booked by working out, taking a shower, practicing makeup, working on my voice, and talking to Marina over Facetime. Once evening came, it was time for us to facetime again.

I had already texted her my excitement at my softer skin, and she was very happy to hear it.

Marina said, "To celebrate that the hormones are working, I thought we'd watch some porn together because I can't be there with you. I've just sent you a link. We should start it at the same time, but I want you to masturbate like a woman so you must follow my lead."

I agreed. The video started of two blonde girls flaunting their assets. Both were wearing just panties and bras, one in pink, the other in purple. They kissed, then the girl in purple removed the other girl's bra and kissed her nipples. On facetime I could see Marina getting undressed, so I did too. Naked, Marina laid back and got comfortable, so I did too. She then started playing with her nipples, so I did too. The pink girl then took off the purple girl's top and started licking her nipples as well.

Soon, the pink girl pulled aside the purple girl's panties, revealing a penis. "That could be you soon, Autumn," Marina teased. I was entranced. Marina started playing with her clit as the pink girl started sucking the purple girl's cock. I began playing with the head of my penis, but just the head. The pink girl pushed the purple girl to a sitting position and then sat on her cock, then rode it. Marina was rubbing her button furiously. "Autumn, if you feel you need to cum, you may." The girls changed position so the pink girl was on all fours and the purple girl fucked her from behind. I squirted, and Marina did soon after.

"Wow, that was hot," I said. Marina agreed. "Hey, my cum is clear!" I said, not expecting that. "Yep, that's another side effect of the hormones. In time the amount of cum will taper off. Now, don't waste it... lick it up slut." I did as ordered. The taste seemed to change to something sweeter as well.

My challenge for Sunday was to get my eyebrows threaded in a gender neutral way. Marina explained that I can just walk into any beauty salon and ask to get it done. Again, to avoid being seen I found one over 20 minutes from home and walked in. There was nothing to it. The woman who did them didn't give me any funny looks when I asked for them to be neutral.

That Wednesday at lunch I had another apointment with my therapist Christine. She greeted me and said, "Next time you come you can bring a change of clothes if you'd like. My office has a private bathroom you can use to change."

"Yes, but then I'd want to put on makeup and then have to take it off."

She made a suggestion, "Why don't we make you my last appointment for the day then? You can leave work early and be here for a 4:30 appointment."

From there, we dove into more of the details of me dressing in my cousin's clothes when I house sat, but it was hazy and we switched tracks to how I feel about my current situation: Am I having any second thoughts? (No.) What am I looking forward to? (Boobs and a full body orgasm, based on what I had been reading.) What am I most worried about? (That awkward phase where I can't hide my chest but maybe my face doesn't pass.) Will my employer understand? (Yes, they have a very good non-discrimination program.)

----

Four long weeks were over, and Marina was back tonight. I was allowed to pick her up at the airport as long as I was fully dressed. So I wore a dark purple, knee-length, bare shoulder dress over a matching purple bra and bikini panty set, did my makeup, and then put on my wig. She had made me promise not to masturbate for the past week and promised a big reward when she came back.

I met her in the airport at baggage claim and we gave each other a discreet kiss. "You look very pretty, good job Autumn," she said to me. Marina was wearing a similar red dress, with makeup that seemed to imply we were going out.

"Where to, miss?" I asked jokingly.

"Home, Autumn." In truth it was rather late, almost 10pm. She lived close to the airport so we were at her place soon after 10.

"I have had some ideas..." she said as we got in the door. "For tonight, I want to celebrate the hardness behind your nipples and their sensitivity. Your breasts are growing and I can't wait to see them develop. But tonight, I'm going to help you find your sissygasm."

"What's that?" I asked.

"I'm going to help you cum from only anal stimulation. But first, you need to prep." She handed me an enema and told me to go to the bahroom and use it. "Also, put these on after a shower, nothing else." They were a pair of black stockings and garter.

I went to the bathroom and read the instructions. I took off my dress and panties and inserted the enema and squeezed the liquid into my butt. Within minutes I needed to poop. And again. And again. After nearly an hour I was sure I was done, so I took a quick shower and put the stockings and garter on.

I stepped out to the bedroom and Marina was waiting for me also wearing just a pair of stockings and garter, but hers were white. She gave me a kiss and said, "OK, babe, get on the bed on all fours." She had an extra towel on the bed and I centered myself over it. She guided me into position, caressing my body--especially my budding breasts--as I settled in. She arched my back and kissed me again. A monitor was in front of me and she started a video of lesbian strap-on porn.

She was always caressing me with one hand as she used her other hand. She put on a latex glove and covered it in lubricant. I was actually feeling excited with anticipation. She added lubricat to my hole, and then slowly gently worked a finger inside me. "Relax, babe, I'm going to take good care of you," she soothed.

I let my muscles relax and focused on keeping them relaxed as she worked another finger inside me. I was hard. Marina started massaging inside of me with her fingers. "This is what we're going for..." she said as her fingers gently flicked over one rounded part within me, kind of behind my taint.

"That does feel good," I said and my cock stood at full attention.

"Good babe, now don't touch yourself, let me do all the work." Marina laid down half under me, but still kept her fingers in place. She was able to kiss one of my nipples as she stroked my prostate. Keeping her fingers inside me, she sat back up and kissed me as I turned my head and snuggled close to me. Her skin and boobs were pressed against my side. She also played with my nipples with her free hand.

"I love feeling your boobs against me," I admitted. So she made sure to keep it that way. Between the strapon lesbian porn, Marina's skin touching mine, her fondling my boobs, and her caressing my prostate, I was in the right frame of mind to have a great orgasm. And I did. Best ever. I moaned out like a slutty girl and Marina turned my head with her free hand to kiss me and she continued to rub my prostate. The orgasm pulsed through my entire body and I had to lay down after quivering a few times. Only after waiting for me to be done did Marina slowly slip her fingers out of me.

She took the glove off, put it in the trash washed her hands, then laid back down leaning against me. "That was so lovely... I'm so glad you were able to enjoy your first sissygasm." I purred with delight. We kissed, then she helped me roll over and straddled me face. I licked her clit to a quick orgasm.

We showered together, then she gave me a gift: a purple satin nighty that matched a pink one she had bought for herself. Finally, we fell asleep together.


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ashleyw_xoxoashleyw_xoxoover 3 years agoAuthor

I'm sorry it left that impression with you ShadowRosie. The intent is to portray someone who is a little reluctant and maybe has some second thoughts from time to time, but through encouragement breaks down their internal barriers.

ShadowRosieShadowRosieover 3 years ago

I'm sorry, I keep feeling this is being done under duress and is therefore, illegal.

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