Sissy First Time Anal

Sissy First Time Anal
You are here: Home / True Sex Stories / Sissy tries anal for the first time
I wanted to share with you today about the time I met with a very new and eager sissy who wanted me to be her first. This sissy intrigued me a lot and we had a lot of fun together. I am here to tell you all about it and for any new sissies or curious men and women out there who want to know what might happen when you first meet someone like me, a lover of all things sissy. If you have any questions for me feel free to leave them down below.
I have posted a few times on this blog and it was through those stories that this particular sissy found me on aff (where I frequent a lot) and we decided to link up. Usually, I would play a little harder to get but this sissy had really intrigued me and after we had video chatted, she showed me that she was really ready to have her first real-life experience with a man.
Her name was ‘Sasha’ and she was cute, passionate, and a real submissive sissy who I thought needed some serious sissy training . She told me everything she wanted to try and she was prepared to do anything to get her there. I wanted to help her fulfill her desires and so we arranged to meet up after a few more video chats and lots of teasing.
She traveled to me and I booked an apartment on a popular booking site. We met at a gorgeous bar before I showed her the place I had booked and she was thrilled. I decided to stay at my place for a little while and let Sasha, stay at the apartment so she would have time to relax and get ready for me.
I like to start any newbie off with a blowjob. My dick is quite big and it gives them a chance to explore sucking, handjobs, and deep throating without too much pressure. Sasha had already told me she had done absolutely nothing with a man before and so it was me who suggested easing her in with a blowjob and some light cum training and she knew how big my cock was, which just excited her more.
As I’ve said before in my previous articles I don’t mind if you’re bad at something at first, it will take me no time to get you up to scratch and I knew that no matter how bad Sasha was at sucking dick, I would get her to pro-level soon enough.
I bought dinner, flowers and treated her like an absolute queen, but the second we went to the bedroom, she was my beautiful slut and she loved that.
I lay back on the bed, all I wanted was to feel her lips around my shaft. She slowly made her way down my body and unzipped my pants and as soon as she got ahold of my cock I was shocked at how good she was at handling me. At first, she struggled to get my cock into her petite mouth but once it was nice and wet from her tongue I slipped in and out of her throat with no issues.
She begged me to take her right there, but I just wanted to use her mouth. I told her that you need to take things slow, but she was feeling so slutty that while I was laying down she sat on top of me and pushed my cock inside of herself.
Unbeknownst to me, she had already applied my favorite lube to her tight ass, she knew all along what she was planning on doing.
Now, my bbc cock is a can of soda thick and this was her first time, but she just wanted it so bad she shoved it inside her. This was naughty and she knew against my sissy rules, but she was so cute and so tight that I even thought about letting her off.
Update : If you want even more intense, uncensored erotic stories, user submissions, and videos come and join me inside of the VIP membership .
She was naughty and she needed to be punished somehow for being so defiant and doing something I told her not to, so I lifted her off my cock, lay her on her front, and showed her exactly how to cum like a good sissy.
I squeezed my way into her ass and penetrated her deeply, she was moaning loudly, begging me to keep going. Her ass was so tight around my shaft that I really had to concentrate hard on not cumming.
There’s a big difference between cumming from masturbation and sex and from cumming from being deeply penetrated and fucked deeply with every thrust stroking your prostate.
It’s something so magical when you show someone that for the first time. Sasha came so hard, she was gripping onto the sheets and moaning hoarsely, her entire body was trembling and I couldn’t help but cum too, deep into her ass and filling her up, so deep I could have impregnated her .
After I came inside her beautiful ass, I fell asleep, we cuddled and I stayed over. I never do this, but for some reason with Sasha, it just happened and I couldn’t resist.
The next morning I left for a few hours and came back to a repeat of the night before. She was ready for round two and how could I resist that ass? It felt even better the second time around and I could tell she was now a complete anal lover. I had broken this sissy in much quicker than I usually do with my other sissies but I knew she was special and I know she will keep on coming back again and again.
I want to know if you’ve had any experiences like this or what you enjoyed from your first time as a sissy or the one fucking the sissy. People have so many great experiences to share but are at times too afraid to share them, but this is a safe space, leave your experience below, I can’t wait to read it.
I hope to find someone like you. ♥️
Your email address will not be published. Required fields are marked *

Ошибка при установлении защищённого соединения

Страница, которую вы пытаетесь просмотреть, не может быть отображена, так как достоверность полученных данных не может быть проверена.
Пожалуйста, свяжитесь с владельцами веб-сайта и проинформируйте их об этой проблеме.

Во время загрузки страницы соединение с xhamster.com было прервано.

Отправка сообщений о подобных ошибках поможет Mozilla обнаружить и заблокировать вредоносные сайты

Сообщить
Попробовать снова
Отправка сообщения
Сообщение отправлено

использует защитную технологию, которая является устаревшей и уязвимой для атаки. Злоумышленник может легко выявить информацию, которая, как вы думали, находится в безопасности.

All Videos Channels Pornstars Gifs Photos

Play All

View Playlist

Play All

View Playlist

Orientation

All

Gay

Transgender

Porn In Your Language

russian

alessandra jane
хентай без цензуры
lena reif
красивое порно
руки базуки
jojo
natalie mars
cute
red fox
loren strawberry

Fake Tits
Natural Tits
Small Tits
Huge Tits
Red Heads
Blondes
Brunettes
Piercings
Tattooed
Asian
Arab
Latin
Black
Indian
White
18+ Teens
MILFs
Mature

Top Rated Gifs

Fuck-

Milking a shower of cum

Most Viewed Gifs

yve bukkake

Wonderful swinging boobs

NO MORE ADS. JUST ALL THE PREMIUM PORN YOU CAN HANDLE
WELCOME TO THE BEST PORN EXPERIENCE. EVER.
FINALLY, THE PORN EXPERIENCE YOU DESERVE.

Pornhub Literacy 101 , learn more about our commitment to trust and safety!

All

Professional

Homemade

40:46
HD

Free

Searches Related to "sissy first time anal"

1
2
3
4
5
10
Next

Information
Sitemap
Terms & Conditions
Privacy Policy
DMCA
2257

Work With Us
Content Partners
Advertise
Webmasters
Model Program
Press

Support and Help
Content Removal

Contact Support

FAQ
Trust and Safety
Parental Controls
Feedback

Discover
Pornhub Blog
Insights Blog
Sexual Wellness Center
Mobile

Visually Impaired
More

Данный сайт предназначен сугубо для лиц 18 лет и старше. Если вы моложе 18 лет, то, пожалуйста, покиньте этот сайт. Этот сайт содержит изображения, видео, аудио, текст для взрослых людей, занимающихся действиями сексуального характера. Если доступ и просмотр материалов для взрослых не законен для Вас, пожалуйста, покиньте сайт прямо сейчас.
Продолжая и подтверждая, что вам 18 лет и старше, вы самостоятельно подтверждаете доступ к просмотру сексуально откровенных материалов для взрослых, такиx, как фильмы для взрослых, хардкор фильмы для взрослых, XXX фильмы. Выбор за Вами, подчиняться ли местным законам, касающимся материалов для взрослых. Вашим выбором Вы берете на себя ответственность за любые Ваши действия на сайте, личные последствия от использования сайта и соблюдение общественных и социальных норм. Создатели этого сайта и поставщики услуг не несут никакой ответственности за Ваш выбор - продолжить использование этого сайта.
Данный сайт не предназначен для совместного использования с лицами младше 18 лет и предназначен сугубо для персонального единоличного использования. Для согласия с вышеприведенной информацией, подтвердите свою дату рождения и нажмите кнопку ВОЙТИ.
Эта мера только для подтверждения Вашего возраста, мы не используем и не сохраняем Вашу личную информацию
Offering exclusive content not available on Pornhub.com. Super affordable at only $9.99/month.
No Ads + Exclusive Content + HD Videos + Cancel Anytime
Luckily you can have FREE 7 day access!
Luckily you can have FREE 7 day access!
No Ads + Exclusive Content + HD Videos + Cancel Anytime
No Ads + Exclusive Content + HD Videos + Cancel Anytime
Offering exclusive content not available on Pornhub.com
Pornhub provides you with unlimited free porn videos with the hottest adult performers. Enjoy the largest amateur porn community on the net as well as full-length scenes from the top XXX studios. We update our porn videos daily to ensure you always get the best quality sex movies.

16 min Freakluver101 - 4.2M Views -
13 min Backroom Casting Couch - 4M Views -
9 min Silicone Girls - 6.7M Views -
3 min Sissytrainers - 1.9M Views -
8 min Mofos Old School - 3.5M Views -
16 min Curious Porn Pass - 70.1k Views -
5 min Younganaltryouts - 2.4M Views -
14 min Exploited College Girls - 2.8M Views -
50 sec Sluttycdsam - 23.1k Views -
22 min Hardercucked - 840.4k Views -
23 min Marcusmortaud - 686.3k Views -
11 min My Very First Time - 526.3k Views -
8 min Mofos Old School - 3.7M Views -
13 min Amateur Lapdancer - 2.6M Views -
8 min Casting Alla Italiana - 334.9k Views -
11 min Filthy Amateur - 302.6k Views -
3 min Anastasia Mistress - 67.5k Views -
XVideos.com - the best free porn videos on internet, 100% free.

Pilar Lastra Naked
Cum Shock
Elaine Klimaszewski Nude

Sissy First Time Anal

Report Page