After my wife died, I sank into a kind of funk. Some people would call it depression. Family and friends tried to help. They brought me meals and found activities to invite me to attend. The truth is I missed that close personal, comfortable, relationship that Mary and I had for almost 45 years. I especially missed the rush that I got from driving her into orgasmic moans as I buried my cock balls deep in her wonderful warm wet pussy.
I wanted to experience those feelings again, but I didn’t know how to make it happen. I didn’t want to try to meet woman at bars, and I certainly didn’t want to pay for sex. So, for some time my main sexual release was my own hand as I watched porn on my computer in the privacy of my house.
One day, as I tended to Mary’s flower gardens in our back yard, I noticed my neighbor, Casey, sunning herself in the next yard. I had never noticed what a hot body she has. She is about 5’6” with long auburn hair. She works as a personal trainer/masseuse at a local athletic club. Her body is trim and tight.
Casey was wearing a tiny white string bikini. It was essentials three small triangles of semi-transparent cloth, held together with some string ties.
I guess I spent too long gazing at her. She rolled over, looked right at me and said, “I see you eying me up. Have you become a peeping Jack?” Then she laughed.
Casey and her husband and Mary and I had been close friends. There was never anything sexual between us, we were just all good friends. We were very comfortable with each other. Casey’s husband had died about six months before my wife, Mary passed away.
“Busted!”, I admitted. “I guess it’s been too long since I’ve seen a beautiful woman in the flesh.”
“You should get out more. Meet new friends. I personally know that there are several women right in our sub-division who would love to get to know you. You know that women tell each other everything.”
I told Casey, “I’d love to do just that, but I don’t know how to start.”
She replied, “The question isn’t can you start; it’s can you finish?”
“I don’t have any problem finishing; and I can do it in a very satisfying way!” I couldn’t believe I had said that, but as I already told you, I am very comfortable with Casey.
Casey got up to head inside her house. As we said goodbye, she stopped and looked back at me, “I found a great sale on Porterhouse steaks today. Would you care to join me for dinner? We can grill them here.”
My first reaction was to make up an excuse that I was busy. Before I had a chance to back away, Casey chimed in, “Good! I’ll take that as a yes! Let's plan on about seven. Dress is casual. We can take a dip after dinner.” I realized that in spite of my shyness I was committed, like it or not.
I had enough time to stop at the wine section and asked the clerk for a couple of bottles of their best Merlot. I also picked up a large bouquet of red roses. I took a deep breath, opened the gate between our lots and knocked on her patio door. I still had reservations about what I was doing. I reassured myself that this was Casey, my old friend. I thought to myself, “Relax Jack. This will be just like old times”
“Come on in. We’re almost ready.”, was Casey’s cheery response as she walked toward the door. The sight of her was breath taking. She was still wearing her semi-transparent white bikini top. With her now facing me, I could see how it cradled her magnificent breasts. As she walked toward me, I could see her breasts bouncing. I could not take my eyes off them. Oh how I’d love to fuck my cock between them.
“These are for you,” I announced as I held up the roses. “And these are for us.” I nodded toward the bottles of Merlot.
“Oh Jack, the flowers are beautiful! Thank you so much” Casey squealed. “Put the wine on the table. I’ll get some glasses. Can you fire up the grill? The steaks are ready to go when you are.”
I disposed of the wine as directed and headed to the patio to fire up the grill. As I was preparing the grill, I felt Casey come up behind me. She wrapped her arms around my chest and pressed her body against my back and my butt. It’s a good thing she was behind me or she would have felt my hardening cock as her nipples threatened to burn holes in my back. I could feel how toned her body was as she squeezed me tightly, “Thanks for the flowers. I know we are going to have a great time this evening.”
The dinner turned out to be fantastic. The food was delicious and the conversation was exciting. The wine added to the relaxing environment. Casey suggested that we take desert on the patio. She had some romantic music playing softly all evening during. As we walked into the patio, “Near You” by Francis Craig started up. “Oh I love this song. Will you dance with me?” She grabbed me by the hand and pulled me close to her body.
I was certain that she could feel my cock stirring in my pants. She almost whispered in my ear, “After Harry died, I couldn’t imagine sex with another person. Then on a business trip, an old friend showed me that life is for the living. I’d like to be that person for you…tonight.” I looked down at her as she looked up to me. Cautiously, I moved my face closer to hers. Then we were kissing. The kisses were very tentative, even gentle at first. I felt her mouth open so I opened mine, Our tongues began to dual.
Somewhere in this embrace, we stopped dancing. I was caressing Casey’s back. She began to unbutton my shirt. I felt her strong hands caressing my chest. I could feel the heat from her body.
“I have a treat for you, Jack”, she whispered in my ear as she opened my belt. “It’s my specialty.” As my pants dropped to the floor, Casey untied her skirt and guided me to the corner of the patio. She had a Massage table setup. She directed me to climb on the table and lay on my stomach. I felt her pour some warm oil on my back. She began to caress my back starting at the shoulders. She rubbed the oil lower and lower. When she got to my briefs, she slowly pulled them down below my ass.
“Help me take these off”, she asked as she pulled them toward my feet. I raised my hips and discreetly moved my cock out of the way. She pulled them all the way off and dropped them on a chair. Then she began to knead my ass. Again, I was impressed with the strength of her hands.
She massaged my thighs. Every so often I would feel her hands brush my balls. The sensation just made my cock harder. She proceeded down my legs all the way to my toes.
“Roll over. It’s time for the front.” As I flopped on my back, my cock stood straight up, swaying in the air. “Doesn’t it feel great to be touched?” She whispered. “I love being naked outdoors.” With that she pulled on the string holding her top in place. The top fell away revealing the treasures that I had been ogling all evening. Then she pulled the strings at each side of the bottom and it fell away. She was naked in the moonlight. What an exotic sight.
“Aren’t you concerned about being naked here on your patio?”
“It’s very private here. The only neighbor who can see us is that Peeping Jack who lives next door. I understand that he is occupied tonight.”
Casey returned her attention to my feet. She worked her way up my legs. Just before she would have gotten to my cock, she stopped. I opened my eyes to see what the delay was. Casey was holding a large bottle of something against her chest just above her right breast. As she squeezed it, oil poured down her body. She moved the bottle around so the oil covered both breasts .
Once she had her body all lubed up, she moved to the foot of the table and began to crawl up my body. As she did, she covered me with the same lube. She slid her body up and over my rock hard cock, pressing it back against my belly. When she reached my head, she took my face in her hands.
“I can feel how much you are enjoying this lesson.” She kissed me deeply. I responded by driving my tongue down her throat. Casey began sliding her body up and down mine. She was masturbating my cock with her oil slick body. The feeling was beyond wonderful.
“Oh Casey, I can’t take much more of this lesson. You’re going to make me cum.”
“You will cum soon lover, but not just yet.” With those words, she slid off my body. She positioned her body next to my cock and poured more oil all over it. She wrapped both hands around my now throbbing cock and began to stroke it slowly. “Mary told me that you had a nice cock, but her deion didn’t do you justice. You do know that women tell each other everything.”
I really couldn’t concentrate on what she was saying. All the blood in my body was racing into my cock. The sensations were overwhelming. “Oh yes, fuck yes, make it shoot. I’m so close. Oh my god, I’m ccccccccccuuuuuuuuuummmmmmmmiiiiiiiinnnnnnnggggggggggg.”
Casey pointed my cock right at her magnificent tits as she continued to milk it. Spurt after spurt of hot cum blasted her tits. It was the biggest load I ever shot. I closed my eyes for a moment to relish the feelings of release that swept over my body. When I reopened my eyes, Casey had crawled up on the table next to me. She laid her head on my chest and continued to fondle my shrinking cock.
“Once we recover, we can take a shower and then go for a dip in the pool. You know how I love being naked outdoors.”
My first impression, as I began to return to consciousness was warmth. Casey and I were each lying on our sides, spooned together. My right arm was wrapped around her waist. The odor of sexual excitement, combined with Casey’s natural scent, and the hint of the delightful perfume she was wearing permeated our personal space. Add to that mix the flowery smell of her lotion and you have an erotically stimulating environment. Without consciously thinking about it, I began to caress her firm breasts. My hand slipped lower across her tight abs and I felt her neatly trimmed landing strip.
My senses were overwhelmed by the situation. Casey was this wonderful combination of strength and femininity. She had just given me the best sexual climax that I had experienced in a long time. Now she was sleeping in my embrace.
My hand dipped lower and found the shaved entrance to her sex. I was amazed! Despite the fact that she had done all the work and provided all the pleasure, her pussy was dripping wet. My finger slipped effortlessly into her warmth. My thumb came to rest on her clit/ I could feel it emerging from its hiding place under her hood.
As I strummed her clit and finger fucked her pussy, she began to stir. I felt her body tremble as she sighed, “Oh that feels so good! Please don’t stop.”
Her reaction triggered one of my own as I felt my cock rise and press against her ass. “What a nice surprise you gave me. I’ll never forget tonight.”
“Tonight’s not over yet.” she responded.
We lay together in this very sensual embrace for a long time. Finally, Casey stirred, “Let’s get a shower. Then we can play some more in the hot tub.” She slid off the table and grabbed my hand. The outdoor shower was just a few steps away. Casey adjusted the temperature and we both stepped in it together.
I was having a fantastic time. The moon was shining through the trees. The temperature was still in the low 80’s and the light breeze danced sensually over our bodies.
We began to soap each other’s bodies. It was such a thrill to run my fingers over Casey’s smooth skin. It was even better feeling her touch on my body. I had some conflicting thoughts running through my mind. I had been conditioned since I was fourteen that these feelings of pleasure needed to be intertwined with ideas like love, commitment, and long-term relationships. However, here we were two friends giving each other the ultimate pleasures with no strings attached. So this is what “Friends with Benefits” is all about.
I was brought out of my reverie by the thrill of Casey gently soaping my cock. Instinctively I began to soap her sensitive breasts. “I love it when you touch me like that.” We leaned closer and began to kiss passionately. I wrapped my arms around her body and pulled her close to me. I crushed her breasts against my chest. My cock poked against her rock hard abs. I could feel it rubbing across her landing strip.
I whispered to her, “How about a dip in the hot tub?”
We turned the shower off and moved to sit on the side of the hot tub. I kissed Casey solidly on the lips and then moved my attention to her neck. My thumb and forefinger found one of her hard pointy nipples as my lips found the other. I sucked her entire areola into my mouth. I felt her body tremble. Casey was moaning softly as I caressed her tenderly.
I slid into the water and turned back to face Casey. Her legs were dangling in the water. I took hold of each ankle and placed them on my shoulders. I began to kiss and lick the inside of her thighs. I grabbed her ass and pulled her closer to the edge of the hot tub. My tongue, like a heat-seeking missile, found its target. I licked her pussy from top to bottom, paying particular attention to her very sensitive clit.
Casey began to squirm as she moaned, “Oh jack, that’s wonderful. Please don’t stop. Oh fuck, I’m so close. I need this, Jack. I need to cum all over your face.” I tightened my grip on her ass and drove my tongue as deep as it would go. I licked her lips and her clit. I began moving faster and faster. I wanted the thrill of making Casey cum. Casey was almost screaming. She grabbed my head and forced my face harder against her warm wet pussy.
I felt her body tense. Her legs clamped around my ears. “Yes. Yes. Yes. Oh, fuck yyyyyyeeeeesssssss. Don’t stop. Don’t you dare stop. I’m cuuuuuuuuuuummmmmmmmmmmmiiiiiiiiiinnnnnggggggggg.” With one final spasm, Casey collapsed. She was spent for the moment. I eased her body into the hot tub and enveloped her in my arms. I wanted the feeling of this closeness to last as long as possible.
Casey finally opened her eyes and looked at me, “Jack, please fuck me. I want to feel your beautiful cock in my pussy.” She climbed out of the hot tub and led me to the double chase lounge that she normally used to sun herself. She flipped onto her back opened her legs wide and held out her arms to me. What an invitation that was. I crawled on top of her. She pulled my chest tight against her heaving breasts.
She wrapped her legs around my ass and pulled my cock toward her pussy. It was warm, wet, and very slippery. I tilted my hips slightly and slowly but firmly slid my cock all the way into her body. The muscles around her pussy were just as toned as the rest of her body. They grabbed my cock like a hand in a velvet glove. I felt the tip of my cock rub against her cervix. Then I slid almost all the way out and plunged in again and again. Casey was kissing me passionately. I felt her cum again and then on the next stroke yet a third time. She was hanging on for the ride of her life. We broke our kiss long enough for her to tell me, “I’ve dreamed about you fucking me ever since Mary told me what a great lover you are.”
That spurred me on to fuck her faster and harder. I heard her almost sob, “Give it to me, Jack. Let me have it. I want to feel you shoot your load deep in my cunt.” She was begging me to cum.
I felt the beginnings of my orgasm in the back of my neck and in the tips of my toes. The delightful sensations spread down my spine and up my legs. My body went rigid. I buried my cock balls deep in her pussy. The wonderful sensations finally exploded out of the tip of my cock as spurt after spurt of my semen blasted into Casey.
I held Casey tightly as we came down together from our orgasmic high. I was so appreciative of my new sex teacher. Life was good, better than it had been for a long time. I was back in the game.
Over the next few weeks, Casey and I spent a lot of time together. I had never been in a relationship like this before. I guess we were what people call "Friends with Benefits." We were not exclusive. We both had our seperate interests. But when the opportunity arose, we would have the hottest wildest sex that I have ever enjoyed. I learned that Casey had a bit of a submissive streak. One of her favorite positions wasto be pinned to the bed on her back. I would hold both her wrists in one of my hands above her head as I slowly slid my hard cock in and out of her dripping wet pussy. As I started, she would moan her approval.
"Oh Jack, you feel so good inside me!" she would lift her ankles and lock her heels behind my ass. She would pull hard again! "Oh God, yes. That is so fucking good. Yes. Oh Jack, yes. FUCK ME HARDER! I'm going to cum. Oh yesssssssssssssss!"
Casey made me feel so virle. I was a MAN! I was providing her (and myself) with intense pleasure. I swear I could feel my cock get harder than at any other time in my life. As I fucked her harder and faster, she would wrap her legs tighter and tighter around my hips and ass. The nit would happen. Casey's beautiful body would stiffen. She would scream, "Oh my God I'm cumming. Oh fuck yesssssssss. Give it to me. I want your cum in my body!"
That would usually drive me over the edge. With one final thrust, my cock would start to shoot. With all my being my body would spasm, driving spurt after spurt deep into her womb.
Then we would both relax and settle into a wonderful embrace, truly joined together as one.
One evening after one of these wonderful complete fuck sessions, Casey mentioned to me that there were a number of women in our circle of friends who would love to experience what she had just enjoyed so much. She again reminded me that women talk to each other about everything.
I was so very comfortable with Casey. I had not yet seriously confronted the idea of establishing a sexual relationship with anyone else. I also got the distinct impression that Casey had an objective that she was steering this conversation toward.
"Oh Jack, I have a favor to ask of you, but before I do, you must promise me that this will never disturb the wonderful relationship that we have together."
"Wow, Casey, this sounds very serious. I promise whatever you want of me will never change our friendship."
Casey then told me about an old friend of hers named Sue. Sue was a professional woman in her early 60's. She is the CED of an executive consulting firm that she helped establish years ago. Sue had lost her husband a couple of years ago. She had thrown herself into expanding her business and also into a number of community service projects. That didn't leave any time for developing personal relationships. Sue was now the president of the Friends of the Symphony and as such was organizing the yearly spring social. This is the major annual fund raising activity of the organization. It is a formal dinner dance at the most exclusive country club in town. As the chairwoman of the event, Sue needsan escort, but she has no one to ask. Casey wanted to know if I would be willing to at least have dinner, meet Sue, and if we hit it off, to escort her to the ball. "Who knows, Jack, you might even get luck with Sue.
I agreed to meet Sue and Casey agreed to invite us both to a small dinner party.
Casey arranged a time for the dinner and she asked me to pick Sue up.
As I approached Sue's front door, it opened and there stood Sue. She is about 5'6" tall with coal black hair and a fair complection. She has shapely legs and medium sized breasts. She was wearing a black cocktail dress and black pumps. My first reaction was that this could be fun. We introduced ourselves and headed to Casey's.
Dinner was a lot of fun. The food was great. Sue and I hit it off. Casey was obviously pleased at how her scheme was working out. Sue and I helped Casey clean up after dinner, said our good byes and headed back to Sue's place.
We made ourselves comfortable on her couch. Sue brought some Drambuee on the rocks and we continued our getting to know each other.
Sue told me that after her husband died, she wasn't certain if life was worth living any more. I explained that I understood and I felt the same way after my wife passed away. Maybe she was getting to know me. Maybe it was the liquor talking, but Sue told me that she wanted to get back in the game, but wasn't certain how to make the first move. I told her that I had the same problem until I met a very understanding friend that showed me the way.
"Was that friend Casy?", Sue asked me.
"I don't make a habit of kissing and telling. We are great friends. You'll have to get the details from Casey."
"And here I thought chivarly was dead. I think that is charming. You know we women talk about everything so I know about your relationship."
"Well, Sue, you are an attractive, sexy, woman. I can be your special friend if you really want to get back in the game."
"Oh Jack, I do want that. I just don't know what to do."
"Let's have another drink and relax here on the couch together."
As we sat down,I wrapped my right arm around Sue's shoulder. She didn't resist, but rather melted into my embrace. I took my free hand and tipped Sue's chin up to face me. Gently I moved closer and closer. I slightly opened my lips and we kissed. Sue responded by oening her lips and sliding her tongue into my mouth. As we kissed, I slid my free hand down across her breasts. I felt Sue's rapid intake of breath followed by her contented moan. Her nipple hardened and she kissed me even harder.
I used my hand around her shoulder to find the zipper on her dress and eased it down to the middle of her back. With my other hand, I began to caress her thigh.
Sue began to moan even more, "Oh Jack, that feels so good. Please don't stop."
It was time for the unwrapping. Realizing that women are uncomfortable with teir own body image, I turned the lights down low. I took Sue in my arms. "You are a beautiful sexy woman and I want to see all of you." With that I eased her dress off her shouders. She was wearing a black push up Bra that really displayed her beautiful breasts. As her dress fell to the floor, I undid the front clip freeing those perky tits. As if on auto pilot, my lips found their way to her right nipple. My free hand closed around her left nipple and tweaked it. Sue loved the attention she almost fainted from the pleasure.
My hands slipped lower to find that Sue was wearing a lacy black thong. I hooked my thumbs in the waist band and slowly lowered it to the floor. Sue's pussy lips were shaved with a small landing strip of that same black hair. I slid one hand along those smooth lips. I was pleased and a little surprised to find Sue was dripping wet. She was so ready to be fucked. she needed to cum.
By now Sue was moaning constantly, "Oh Jack, that feels so good. I've missed these feelings so much. I want to see you naked too."
With that invitation, I stepped back to give Sue access to my belt buckle. While she opened my pants, I unbuttoned my shirt. In short order, I was as naked as sue was. All this fore play had my cock rock hard. She wrapped her fingers around it and slowly stroked it. My cock is cut but it still has a lot of foreskin. That means it is very easy to jack off. sue was fascinated with how the skin covered and uncovered the sensitive head.
"Oh Jack, your cock is so beautiful. I've forgotten how good it feels to stroke a big hard cock!"
I gently laid Sue back on the couch. She kept stroking my cock with one hand, while she used the other one to stimulate her clit. I bent over her prone body and began to lick her pussy lips. They opened like a blooming flower. She was really ready. I moved to the foot of the couch and placed her feet over my shoulders. This gave me open access to her wonderful pussy. I began to lick from her ass to her clit. Then I took her clit in my lips and lashed it with my tongue. Oh my god, Sue was thrashing on the couch. she was rolling her head from side to side.
"Oh fuck, Jack, that is so good! You are going to make me cummmmmmmm. Yes! Yes! Oh I'm cummming." With that Sue's body tensed. She stretched her legs straight up in in the air and pressed them against my ears.
We laid together for a few minutes when Sue finally broke the silence. "Oh Jack, I can't remember ever cumming like that before. It was wonderful.
I told Sue that this was only round one. I positioned her sitting upright on the couch and craweled between her legs. I positioned my cock pointing it right at her sex and eased it inside. Sue was so wet that I entered her with no trouble at all. At the first contact, Sue stiffened but as the pleasure overtook her body, she relaxed and wrapped her arms and legs aroung me. I began to fuck her slowly and delibertly. I burried myself balls deep in her cunt. I could feel my ballls bouncing against her ass as the tip of my cock bumped against her cervix. I could tell that Sue felt it too.
She screamed out with the pleasure. "Oh Jack, your cock is so fucking hard. I love the way it fills me up. You feel even better than Casey said you would. Don't stop. Please don't stop. Oh fuck make me cum again. Oh yes, I'm cummmmmmmmmmmiiiiiiinnnnnnnnnggggggg."
That was enough to push me over the top too. I drove my hard cock as hard as I could into Sue's pussy. The force lifted her entire body off the couch. She wrapped her arms and legs around my body and squeezed as tight as she could. There is nothing quite as good as a man and a woman with their bodies joined together and enjoying simultaneous climaxs.
Doing a favor for Casey had never been this fun before.