Making The Leap



What’s your gender? Woman
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States West
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Educational Sales
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Horny
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

Making The Leap

How long ago did this hookup happen? Monday

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? My partner is 8 years younger than me at age 52, is 6″ tall, has thick dark brown, almost black hair with just a few tinges of gray, is like a Rhino, you’ll never not know he is around and has a very gregarious and outgoing personality. He is compassionate, caring, funny, loves to tease, and yet can be very serious. His dark brown eyes are captivating, entrapping you when he stares at you revealing his emotion. Those eyes don’t allow him to lie, so he is very honest.

I met Jeff at work when he came to work for our organization. I trained him in his job and we have grown very close over the last four years. I am guarded with new people in my life, well guarded in general but he warmed me up to his friendliness and after about 6 months, I began to have a yearning to be with him. After 18 months I knew I wanted him. I struggled in between wondering if I could maintain the relationship with my husband for the sake of our 4 adult children and our grandchildren, and have another man in my life. I finally decided and reach the conclusion that 1. yes, I can handle another man in my life and 2. I was willing to put my marriage on the line to have sex with Jeff to see if it was as good as I thought it would be.

I have only ever had sex with my husband, and he betrayed me several years ago with both a porn addiction and cheating on me with multiple women. Sex with my husband is boring. It is simply undress, kiss/make out, he mounts me missionary style, enters me, and in 5 minutes he has ejaculated in me, rolled over, and is done, just as the embers are starting to warm up in me. I wanted more than that and I strategically planned to ensure that Jeff delivered for me.

Why Jeff? I don’t want some random guy screwing me, I prefer to have an emotional connection and I really and deeply care about Jeff, and I know he cares about me. The sexual tension between us is extremely high, I have tried to diffuse it several times by telling Jeff he better not fantasize about us or think of me outside of work. Doesn’t work. I know we don’t always think about each other when we are away from work, with our families, but I also know that Jeff does think about me often, he has told me, and he has told me he cares about me and I do also think a lot about him and I care about him and yeah, I want him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We are in San Antonio this week for a coming educational conference as part of a vendor team for our company. This is what we do. Our materials arrived on Monday and we arrived on Tuesday morning. We ensured that all of our material was there and ready for set up on Friday and then planned out our days on Tuesday and Wednesday and the sessions we are teaching to promote our product. After planning that out on Tuesday morning, I asked Jeff if he would go back to the hotel with me as I had forgotten a Chromebook I needed. “Sure” came his usual reply.

We walked back to the hotel in the hot and steamy San Antonio summer day, and I made that analogy of how I hoped my plan would work and soon Jeff and I would be hot and steamy together. Upon arriving back at the hotel, we were hot and sweating and I invited Jeff up to my room. We had done this many times and he thought nothing of it. Up in my room Jeff sat in a chair in the main room while I retreated to the bedroom. I told him I would be just a minute and he said “Fine” as I heard the TV turn on. I undressed, removing my pants, shirt, bra and panties, adjusted my blonde hair and walked out to the main room.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? As I entered the room, Jeff looked my way quickly, then back at the TV and then he head rapidly turned back to me. His mouth was slightly ajar as he looked over my naked and older body. “I give up. I want you and I don’t want to hold back anymore.” I walked over, grabbed the remote, turned off the TV and then kissed him. I felt his tongue in my mouth as he returned my kiss and I sat in his lap. At the same time I could feel his dick begin to harden under me. I felt his hands go to my breasts, he always looked at them when I wore a low cut top and I knew he was a breast man, and we continued to kiss.

After five minutes, he stopped kissing and with a deep emotional look in his eyes said “I want you more than you will ever know. But I have to know, are you sure?” “Completely” I replied. “You?” I asked? “Willing to risk your marriage and your family for me?” “Yes” as his eyes revealed the longing for me I knew he had. I lifted off his company polo shirt and his tee shirt, rubbing his nearly bear chest, Jeff is not a hairy man thank goodness (I dislike hairy men) and then I undid his belt, his zipper and pulled his pants and is socks off.

We were now naked and my boobs were stimulated with his massaging and my nipples hard, and I could see that his “tool” was hard and I noticed how thick it was. I took his hand, led him to the bedroom and then to the bed. We laid down and I kissed him again, letting go 2 years of sexual tension as I wrapped a leg over him. I took my right hand and began to stroke his dick, and then I shivered. He felt it and stopped, smiled and asked if I had ever been with someone other than my husband? I, of course, shook my head no, and Jeff simply said: “We’ll learn how we work, nothing else matters.” I felt a deep emotional connection with him as he took my hand and showed me how he liked his “tool” played with. Not the stroking motion, but me putting some of my lubricant in my hand and playing with the top of his penis head.
He then began to do something I had never had done. He put some lubricant in his hand and began to touch my pussy lips, massaging them. I felt a tingling as he continued this and then he inserted a finger inside of my love hole (vagina) and curling his finger touch a part of me that just turned me on. Damn, it felt good and I wanted more. I moaned in pleasure, letting out an, “Oh” and a few “Awh yeah” as he played with me. I was his, completely and he could have simply shot his load into me but he didn’t. We were both enjoying making love and realizing how great our sex together was.

By now his own “tool” was very hard and ready and so I got onto my back, and said “Make love to me” Jeff smiled at me, kissing me, then moved me on my side again, lifting my leg, and slowly brought his wonderful pleasure tool to my slice of heaven, said “I love you Nan.” At the same time, I felt his tool enter me, causing a rush of sensation, and deep emotion as he drove his hard tool completely inside of me, holding it there. I felt his hand again on my boobs, his kiss on my mouth and said, “I am so in love with you.” I then began to slowly move his love stick back and forth, Jeff matching my rhythm. For the next thirty minutes we slowly made love, speeding up, slowing down so Jeff wouldn’t cum until we wanted him too.
Jeff now moved me onto his back, put some lubricant in my tool tunnel, and then had me mount him. I had always only had the missionary position so this was all new and most enjoyable. I mounted him, using my lower body and my vagina to guide his meat popsicle inside of my tunnel of love. As his head entered me, I felt warm in my body, my tool tunnel wanting more of this man’s tool. I increased the rhythm as Jeff matched me, and suddenly that warm feeling erupted in my body over and over again as I felt Jeff’s pleasure tool bring me to fruition. I screamed in pleasure, several times as my body tenses and then released itself over and over again. I feel onto Jeff’s chest and felt him driving that wonderful tool deep in me. I could feel his tool harden even more, pulse in me and I instinctively squeezed as more waves of tension and release came over me. I felt a warm streak deep in my tunnel of love as Jeff exploded inside of me. I felt five, no, six, then seven eruptions of his cum in me. No worries at 60 of being pregnant or of STD. We both had been faithful til now. I didn’t care anyway, this was the best damn sex I had ever had.
After our orgasms, we lay in each other’s arms, simply smiling and kissing. “I can’t believe we did that.” Jeff said. “Why?” I asked. “I thought you wanted nothing like that.” came his reply. “I tried to say that to convince myself of that, but I decided that in life, you only have a few opportunities and this is one of them.” “Glad you did?” Jeff asked. “Oh most definitely,” came my reply. “You?” I asked. “More than you can ever know.” Jeff said as he now kissed me again, and started to play with my pussy flaps again. He smiled and I smiled and we made love again, then one more time that afternoon before making love in the shower as we got ready. That night we did dinner and came back and made love two more times, sleeping together in the same bed for the first time but definitely not the last.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We made love most of Tuesday, after a working Wednesday morning and then seeing the Alamo, we made love all of Wednesday and we finished making love this morning as we type this up. As we travel together about 2 weeks out of the month, we have agreed that for now we will keep our affair and hook ups on the road and enjoy our families when home. I am cutting off my husband, after Jeff, I have no desire to let him fuck me because that is what it is, a straight fuck for him, nothing for me.

We know we are soulmates, Jeff and I and as such we are going to be in this for the long haul. Our sex is outstanding but we deeply care for each other if not love each other. No sense ignoring that but we have to navigate in such a way as not to hurt our kids or grandkids. I believe in the end and Jeff has expressed this, that we will be together, living together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A girlfriend who knows that I have had the hots for Jeff for a long, long time. She was excited that we actually took the step, admitted our attraction and did it.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Releasing two plus years of sexual tension between Jeff and I. Coming together, having multiple orgasms was way nice and being with someone who wanted to pleasure me knowing they would get their pleasure also. Just incredible how great sex is with the right person.

What was the WORST thing about this hookup? Realizing that my marriage is over and has been for about 10 years. Now figuring out how to end it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It taught me that I have the right to be happy, excited and thrilled with my sex life. It is possible even at 60 to have a fulfilling sex life, to please a man younger than me by 8 years and discover he completely enjoyed and wants more of me. Wow! It’s like Independence Day!

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? To have a man use his tool with me to bring us both pleasure with him more focused on me, than on himself showed me that great sex begins by focusing on your partner and not on self. You can probably have good sex focusing on your self, but if you want incredible sex, you have to communicate, talk about it during sex, show and tell so to say and then perform.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Sex is an important part of life, no matter how young or old you are. The key to it is communicating and responding be it a one night stand, an on-going hookup or affair, or long term marriage. I will tell you what. Don’t do that and your partner will leave you when they realize there is better out there.

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