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Jennifer's Heart and Soul
My First Anal Orgasm
Posted:Jan 10, 2022 9:24 pm
Last Updated:Jan 20, 2022 11:07 pm
4812 Views

I remember going through the puberty years and constantly obtaining full blown erections that seemed to pop up of nowhere for no particular reason. For example why would my penis decide to get hard while sitting in a classroom just minutes before the bell was about to ring. Ring Ding a Ding why am i just sitting there watching the rest of the class stampeding out of the room like a crazy herd of wild buffalos. Hoping no one takes a gander in my direction, i take one of my hands and try to make an adjustment to a position that will make my penis not so noticeable. Luckily or unluckily, depending on your perspective, my penis was small enough that i was able to do a magic act, now you see it and now you don't. At the time, tight jeans were the fashion so even my less than monster size would be visible at certain angles, if the lighting was right, or if someone had a magnifying glass trying to detect it.

Going through this period of constant erections led me to playing with myself in the privacy of my own bedroom. It felt good to rub on it and pull on it and watch my head turn purple. I was tugging on it every night before going to sleep with no knowledge of why it felt good or why was i addicted to touching my erect penis. I had already been taught the birds and the bees, had a sex education class in , and my neighbor friend's dad drove a semi trailer truck which always had a large stash of porn mags that my buddy would sometimes steal and bring on to our clubhouse to shared with the gang. So i knew that an erect penis was to be inserted into a vagina and i got excited thinking about the notion but being i didn't know where to find a vagina to stick it in.

I will never forget the night when the missing pieces to the puzzle of why my penis was in constant erection mode, why i played with it nightly, why i wanted to stick it in a vagina, and why i started noticing girls . There i was in bed one night and doing what i did every night for at least a half hour but this time besides the stiffness, the purple head, my penis felt different. As i stroked it fast and squeezed it with more pressure i starting feeling an immense tingling and it became more intense with each tug. Then my penis reacted like a lit roman candle firework and exploded a thick watery substance that nearly reached my chin but covered my hairless chess in a sticky puddle of . It was the greatest feeling i had ever experienced in my life. All my curious notions about sex and the penis were answered.

Anyway what was a who just became a man to do? For a spell i began to masurtbate 2 or 3 times a , not just bedtime anymore, but wherever i could. Bathroom time became popular, the clubhouse when not occupied, the woods that were close by, and where ever else i could think of. Along with masturbation i began to experiment with other stimulation because after awhile it was losing it's flavor. I won't go into a whole scenerio of my kinks and pleasures but the one that proved to be enduring and most memorable is anal play.

For some reason or another, maybe it felt good, i started playing with my butthole and started inserting my finger and more fingers as far up as they would reach. Then came the idea of inserting objects other than fingers and this led to my imagination giving me all kinds of suggestions in which i acted upon. Playing with my butthole became a regular part of my masturbation rituals. It felt good but didn't know why i enjoyed to so much. Years and years later i discovered why someone would want be compelled to fuck their ass during sex.

It has been a few years ago when i discovered the mystery of anal stimulation and what obsessed to indulge. Anal became very important to me and began trying different sex toys designed for butt play. Usually i would insert a butt plug while having sex and it made my orgasms stronger. Then in one magic moment i used the right toy in the right way and like the roman candle firework orgasm i experience during puberty i had another explosive fireworks discovery.

The anal sex toy that gave me the most memorable orgasm to date was a vibrating dildo shaped just right for massaging the prostate. I remember i was standing up when i inserted the prostate toy and the vibrations got me so excited that i began fucking my ass in and . When it rubbed a certain spot my body began to shake and tremble. I would let off every time i experienced this sensation not because i didn't enjoy the feeling but it felt like i was about to myself. However the feeling was so wonderful i could not resist and would reinsert the toy numerous times until one point my legs went weak, my whole body began to tremble, the sensation was overwhelming but it felt so good i didn't even care if i pissed all over myself. Then the fireworks erupted. As i trembled with ecstasy a stream of liquid poured of my penis and i knew i achieved the strongest orgasm ever. I stand corrected, it was my first multiple orgasm and the best orgasm of my life.

Did i say multiple orgasms? Yes the vibrating toy kept giving and giving. After the first earth shattering orgasm i kept on massaging my prostate and kept having orgasms. What i enjoy most about prostate orgasms is that you don't even have to touch the penis in order to and orgasms last much longer, more intense, and they give multiple orgasms.

Just wanted to share this with others and if you have never had a prostate orgasm i would suggest at least give it a try. Once you have a prostate orgasm, any normal orgasm just doesn't feel the same. Hope you enjoyed, take care and be safe, hugs jennifer
0 Comments
Thunder Will Certainly Bring Lightening
Posted:Aug 19, 2020 2:00 am
Last Updated:Sep 6, 2020 2:10 am
3802 Views

I thought i would write a short that is more personal and not the usual rant and rave about how screwed society is and how everyone should be include in one large group instead of several subsets where easily becomes a finger pointing war declaring that you are the most important society and those sick crossdressers should be admitted for mental reevalution. I suppose that since i am down in the least important group and probably the smallest and unorganized and unrecognized group because we know how sick we are and hide behind doors committing horrid sexual acts and are ashamed even tell family members how great i in a sexy pair of 6 inch sandal heels with my toes painted so beautiful. My biggest fear is when the world becomes overpopulated and war is no longer viable, i am scared that individual groups well be analyzed and determine which are harmful and should not exist and get strange visitors in the night. Maybe i am a little paranoid but it seems every take over by a group justifies a means of eradicating another group.
Oops i did it again. Sorry for taking a stab at a made up monopoly game society that always confuses the hell out of me and painting my nails always helps calm my nerves. One other thing i enjoy and find great comfort in is severe thunder, especially the ones so loud it almost breaks windows and love to count the seconds for lightening to follow. you can almost track and know how far away the storm front i just by the quickness of the bright flash.
I began to wonder the other day why i love severe storms that can sometimes create destuction and even have a deadly tornado hiding in its mist. I started thinking maybe i relate to tornadoes because the hide in secret and suddenly emerge with vengeance. No this can't be the reason because the last one i saw on the tube wasn't wearing a skirt and wasn't ashamed to show itself and was ready to hammer down on any person thinking they were more powerful. the tornado is definetly not weak, maybe mentally ill, but when it comes out of hiding we all know at that moment is in charge. Right on tornado show those weaklings the don't know shit. i love to sit out on the porch, i open all my windows to maximize the presence and smell of rain, and the stronger the storm the calmer i am and just love the event. I have never felt threatened or scared even when the crossdressing tornado comes out of the dressing room, so what gives? This may sound like a person grabbing for straws but in my deep and intense investigation i can assume originates from my childhood experiences with storms. Back in the day before all the fancy pancy high tech information at you fingertip a loud horn would sound telling everyone to head to the basement just in case that pest bully of a tornado may come out wildly tap dancing in heels of destruction.
It takes me forever to get to my point but by elaborating every detail that pops up in this mentally deficient brain of mine it help me get the feeling i need to discover why i find pleasure in some activities while others stress me to no end. trust me i am also trying to figure out my displeasures also so i can hopefully be a more understanding and compassionate person despite painting my nails in beautiful head turning delight. So is. My mom when hearing the Paul Revere signal that the enemy was approaching we were rounded up like real little troupers and march the basement that was fortified in heavy stone and concrete that would stand up to any punk tornado. I guess maybe the tornado wasnt' the toughest on the bloch. That wall never fell like Jericho. After getting down to the heart of the fort was a heavy wooden bench that served as a work bench. That work bench was made of heavy timber, you just don't see things made like that anymore i would bet that even if the tornada decided to pick up that heavy bench and throw a half a ,mile would probably stay in one piece. So we crawled under that tough sob and felt even more protected. But that wasn't the reason for my love of the storm because my mom certainly was not relieved of worry and never ever settle down until the horn stopped singing. My love for the storm and became a friend of mine because brought the family together in one place for sometimes a couple of hours. We felt more secure all packed in like sardines and forced us to acknowledge one another and gave me the sense we all became one unit and cemented together the same purpose and let us know we were all equal and all of us deserved a chance of survival. Being the middle constantly wanted be loved and noticed, this event was very close me acquiring that sense of worth. I felt like i was a part of a loving and caring family. So when i storm comes brewing in i now believe takes me back those childhood events that always made me feel like a part of the group. Do you want know why i like ramble on and make a story out of very little? My dad could be a little short tempered and if something got messed with he usually came to the black sheep and asked me if i did it. This was my moment to capture a bit of my dad's attention so rather than give a yes or no answer i spun a long story out that went over every possible detailed about how it may have occurred. i liked to throw in a lot of curve balls and got very creative with words to keep his interest but also got him to spend more time with me. He never got mad at my stories, i think he actually enjoyed hearing the tale i was about to tell. so thanks dad you gave me a creative skill in word manipulation to keep you wanting to hear. I would make a very good pr person in politics but i would never manipulate words if it ended in a made up lie and classified it as fiction. Until next time, stay true, be you and be safe, hugs Jennifer
0 Comments
Jennifer discovers nipple play
Posted:Apr 8, 2020 8:20 pm
Last Updated:May 9, 2020 2:04 am
6259 Views

Just wanted share a new discovery that i recently stumbled upon that was part of a packaged gift that hormones gave for allowing them plump my little breasts. i was looking for was bigger breasts so i could have a more feminine figure fill out my cute colorful dresses. The hormones and breast and nipple pumps and a massage with hormone based plant powder made my breasts grow faster than i could have ever imagined. It was like miracle grow used create huge produce in the garden some how found its way into my treatment process and my tiny man boobs suddenly ballooned large enough that now they had a little bounce them when i walked and my nipples constantly brushing against my shirt felt good, no it felt better than good because i began take notice and felt aroused. My nipples probably were now 4 times larger and they were very sensitive and almost constantly erect begging for attention. I did what any sane person would do and found a sex toy designed for the nipple so i could give them what they were crying out for. The toy is basically ran on two double a batteries with two lead lines go out with nipple clamps attached to the ends. The clamps were also equipped with mini but powerful vibrators attached with two speeds. To make it even more deluxe the clamps warm while it is turned and after running for a while they get very hot. So things were happening when i shackled these little sex hungry slaves be dominated by a flick of the switch. The first action was clamping the nipples by adjusting them with enough pressure they stayed put but wasn't too uncomfortable. Once they were secure it was game on and i had a blast teasing them with blasts of electrocution and heat that felt like i was branding my owners mark on them. this going the feeling was so intense i could hardly stand it and had frequently shut down, start , shut down, start . I became a nipple teasing torture addict and wanted to with them for hours. make a long story short, i did indeed with them for hours and pulled them, twisted them and even attached wooden clothes pins them. This sounds horrible and i swear i have never been a person seek out pain and always avoid it at costs. It was as if i was a puppet being controlled by an outside force making put my nipples through a hard core training program whip them into shape. What was happening when i kept testing them with more and more abuse they were becoming less sensitive and it was taking greater pressure to achieve the initial orgasmic sensation the first time i indulged. So there i do not get pleasure out of torture so please don't be a hater. It was comparable to a first time drug user getting that first high and instantly becomes hooked. As time goes on the person becomes addicted to the affects the drug provides but suddenly he needs more and more to get the sensation that first awoke his senses. Did i realize i became an addicted nipple playing, nipple abuser, and a nipple slave master and feel guilty about my action and but my little playmates in rehab to sober them ? Hell no! I don't like what i do them, i love what i am doing and have even upped the game make it worth playing. I don't see them complaining, they are begging for more! Okay thats my story i wanted to share and i never knew how fun it was to play with basically a tiny body part that for the most part was ignored, unless my tee shirt got wet. I would encourage any new comers to experiment with nipple play, hopefully you will discover a new playground that you can add to your existing amusement park for adults only! Take care and be safe, Hugs and more hugs, my nipples smothering yours, Jennifer
1 comment
Jennifer Hopes
Posted:Mar 12, 2020 5:20 pm
Last Updated:Feb 10, 2022 11:14 am
6101 Views

I am thankful for the development of the world wide web because i had a dark shameful secret that i alone played alone. A man wanting to dress and emulate a woman in my days was consider a mental sickness and anyone who was caught would face ridicule, judgement, abandonment, and depending on the sobriety and mental state the invasive homo haters capture could possibly end my life. The last possible outcome seems brutal but may have been my choice rather than society branding me as a sick mental case of the worst kind. I had to be very careful in my dress outs and to be ready to spring into Jennifer when an opportunity arose. I thought i was all alone in my feminine desires to feel what a woman feel freely. I sought love, affection, and sense of care to others needs. I was forced to be total masculine and i just went through the motions pretending to be what i was not. I could not explore and reach out to embrace and learn who and what i was.
When Bill Clinton became president he kept talking about the new computer technology that would change the world rapidly because information would be readily available to all. He called it the information highway and at the time i under estimated its strength and how it would someday liberate Jennifer and allow her to be released from the chains of darkness and emerge into the light. I soon discovered there were many others, to some extent, felt like me and i could relate and feel comfortable knowing i was not an isolated weirdo who was the worst mental case of any group in existence. At least progress is being made and people are beginning to accept people of different sexual practices and fetishes. I am thrilled when i see youth having the opportunity to chasing their desires and dreams of transforming into female beauty. But we still have a ways to go because society still has a habit of throwing individuals into a labeled groups that describes their behavior and who they are.
This site throw crossdressers, transgender, transvestites and transsexuals into a one size fit all classification. This is where the problem arises because when you look around at the billions of people living you will not find two people who look exactly alike. Maybe a close resemblance but not exact. The same follows with feelings and desires of sexual identity. We need to throw away group titles and just accept ;people for being people and learn from each other by showing interest in individual personalities. Everyone that is of human origin should embrace each other with love and compassion. To be legitimate in classifying sexual differences of the TSdates.com group i am thrown into it would take hundreds or maybe even thousands of different catagories to correctly place an individual where he belong. To give a short example of what i mean lets take a look at crossdressers. Do all crossdressers dress in full, do all want to be full time women, do all find sexual gratification when dressed, do all want only sex with men, do all dress to be connected to feminine feelings, are all sissies, are all dominant when dressed? The list can go on and on. No two crossdresser are exactly alike in their sexual preferences or how they feel emotionally. The only way to know a specific crossdresser is to remove them from the group and get to know them by accepting who they are and allow them to talk freely about themselves.
The point i am trying to make is nice little packaged groups are a convienant way of lumping individuals together whether they fit or not. By golly if you crossdress it is a sexual act. I crossdress and it was and is never an act of sexual gratification. I dress to help me capture and feel of what it is like to be a woman. I have always seen women being the glue and strength keeping our society from destroying itself. I am in know way a sissy, i despise the word and cringe when a man come knocking on my door without reading my profile with his cock in hand want the little sissy to suck his cock and do as he wishes. I have nothing against crossdressing sissies because they have a right to be who they are, just as i have a right to be a strong, secure, loviing and caring woman. I just wanted to mention one other danger in placing people into groups. Some groups are stronger in ;population and other groups are small and this leaves a ;potential danger of one group disregarding and disrespecting a group and label them as less worthy. We need to stop the hatred and label and wad all them up into a giant garbage bag and launch it into space and never see it again. People are people and individuals are individuals. Let's respect people for who they are and stop trying to label them. If you want to know more about an individual get to know them and hopefully you will walk away with new wisdom and a new friend. Just had to get that off my chest. Stay true and be safe, Hugs Jennifer
4 Comments
Jennifer Wants Curves
Posted:Aug 20, 2019 11:58 am
Last Updated:Feb 10, 2022 11:14 am
5266 Views

I have always loved women's fashions, i love the feel of the soft fabrics and the colorful array of designs. Women like bold, colorful, and comfortable clothing. There are many clothes i would like to wear, such as tight fitting, but lacking the hourglass figure i am limited on what looks good on me or i would have to resort to artificial pads. I hate wearing fake hip and butt pads because it just doesn't feel natural and how embarrassing it would be to introduce my naked body to a new lover and she discovers that some where on the way home i lost my ass and wide swinging dance floor hips. My solution is to begin training and get those sexy curves. I began waist training, doing exercises to develop a butt lift and i massage with breast creme and use a vacuum pump to get them girls plump. I have considered taking estrogen pills to speed up the process but am a little weary of health complications. I desperately want a natural feminine body shape so my clothes will fit properly and i will feel sexy when my hips and butt have that nice little sway and a bounce in my step will ever so slightly offer a jiggle or two in my boobs. It takes a lot of hard work to be a sexy woman but i am committed to developing the best figure that i can. If anyone can offer advice and tips to help me along i will greatly appreciate. Thanks for reading, hugs galore Jennifer!
2 Comments
Jennifer's First Step in Heels
Posted:Aug 15, 2019 6:46 pm
Last Updated:Feb 10, 2022 11:11 am
5606 Views

I bought a pair of kitten heels, a shoe that is low heeled, today so i can soon wear them on my first public appearance. I selected kitten style so i could be short as possilble and try not to stand in the crowd. I personally love to wear heels anywhere in the range of 4 to 6 inches in height. I love the way the heels accentuate and make a shave legs longer and sexier while also creating a cute little arched foot perched on a pedestal that screams fuck . The other parts of a woman's body like breast and butt i really don't worry so much about. My first female garment i ever tried on was a pair of nylon stockings while snooping around in mom undie drawer. I instantly loved the feel of the fabric when my legs rubbed together. I got so excited i never wanted to remove them, but fear struck me thinking what would happen if i were caught by either parent. Dad would be enraged and want to disown me and mom would make me shameful. After discovering that i liked, really liked womens hosiery i schemed on getting my own pair. As i entered into my teens i was wearing them all the timel. I wanted to own more wardrobe but was held back because i had no good hiding place. In my early 20's i started college and got my own studio apartment. It suddenly dawned on me that i could take my passion for fashion up a notch or two, or three or all the way up!! I ordered everything to make and outfit from the JC Pennys catalog including the garments. When the order arrived my doorstep i was so thrilled i ripped that package open at lightening speed. After completely getting dressed and getting my hard cock situated in a comfortable position in the white cotton briefs, i pranced around the room gracefully feeling like a sexy . Suddenly my heart sank because i was missing an important piece of the puzzle. My feet were covered with nylon but i was missing a pair of heels to pull the whole outfit together. I always dreamed and fantasized about wearing heels, not short heels but really tall heels. I did not want to delay my experience , i wanted to get a pair immediately so i could enjoy the whole evening as a woman. I knew from visiting the mall that Bakers Shoe Store carried very sexy womens heels because i always took quick little glances at the ones through the glass exterior as i walked by. Sometimes i would keep making many rounds so i could make multiple glances and discover what heels turned me on the most. I was scared as hell about going in and buying a pair but the fear was overcame by a stronger desire to complete the . I decided to go with getting a simple black pair with the tallest heel i could get. I knew that a salesperson would approach to assist and i knew i needed to have a story. I was too to know that he really could care less why i man was in a womans shoe store buying heels. The explanation came stuttering quickly as i told him i was on a date and her heel broke off so i was being a true gentleman and wanted tho get her a new pair. She need black and her heel was tall i explained. He showed several pair and when the 5 inch black patent leather was waved my nose and i saw the thin shiny chrome heel i nearly grabbed them of his hand. When i got home my excitement was overbearing but i wanted to enjoy every second leading up to sliding my foot in and taking my first step. I dressed slowly with each article of clothing knowing that the climax of the experience would be the heels. It was like each step such as clasping the bra hooks together and positioning it in the right spot was all a part of foreplay and the closer i got to dressing complete and finishing off with the main attraction the more excited i became and the more i was aroused. When the moment arrived and slipping my foot in each shoe while my hand was against the wall to offer support i was close to orgasm without even being touched. Both feet in i was emotionally elated and ready to let go of my support and start walking. I remember taking the step and nearly loosing my balance and falling to the floor, but somehow i was able to stay on my feet. I carefully took steps and it seemed like hours i walked around getting more comfortable with my movements. From that point on i was addicted and still am to wearing the tallest heels and all the different sexy style i could . The kitten heels i bought is to go dressed in public andnot be noticed as a man. I am 6 foot tall and wearing 4 or 5 inch heels would make too tall and i would stand out horribly. When i tried on the kitten heels to see how they felt and looked that is when flashbacks of my first pair made laugh. I am able because of experience easily fly around a room in the tallest of heels without even thinking about my next step. The little black kitten heels were comparable to putting on training wheels on a bike owned by an seasoned rider. I made chuckle a bit but they are kind of cute and will do the job. Just wanted to share my story, i hope you enjoyed it! Take care, hugs from Jennifer!
3 Comments

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Most Recent Comments by Others

Post Poster Post Date
Jennifer Hopes (8)Gina_L07
Apr 9, 2020 10:11 am
Jennifer discovers nipple play (1)HAMONMAN
Apr 9, 2020 2:46 am
Jennifer's First Step in Heels (3)erika125cd
Aug 30, 2019 9:32 am
Jennifer Wants Curves (3)bi4cdfun
Aug 21, 2019 9:57 am