{{ login_id.substr(0, 30) }}{{ login_id.length > 30 ? '...' : '' }}
Settings
Welcome to DLsite!
Create an Account Log in
Announcements
List
Search products （Adult Doujin）
Retail Section
Guide ・Help
Log Out
Search by Work Format
Search for Discounted & Free Works
Search by Ranking
Check out Upcoming Works
Search by popular keywords
Menu
Search
Cart

Middle-aged Man works

Back
Refine
Supported languages
Reorder
Cancel
Displaying  31~60  of 1615
  • Torima, Act 7 [Mi Po Z]
    Video
    Torima, Act 7
    Mi Po Z
    715 JPY 1,430 JPY / $4.65 USD$9.29 USD / 65pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    A small girl learns some lewd lessons with the help of a middle-aged man.
    Purchased: 6,420
    (2,630)
    (15)
    Release date : Jul/08/2021
    Cart
  • The Small Nun in the Confessional [Sushi Shop]
    Manga
    The Small Nun in the Confessional
    Sushi Shop
    385 JPY 770 JPY / $2.50 USD$5 USD / 35pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    A l*li nun seduces and cum-squeezes a middle-aged man in a confessional.
    Purchased: 8,993
    (3,094)
    (15)
    Release date : Jul/20/2020
    Cart
  • Torima, Act 4. [Mi Po Z]
    Video
    Torima, Act 4.
    Mi Po Z
    550 JPY 1,100 JPY / $3.57 USD$7.15 USD / 50pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    A school-aged slut does everything for the old man who calls her out. WMV / 43 min / CV: Runa Hoshitsuki
    Purchased: 3,882
    (1,859)
    (15)
    Release date : Apr/02/2014
    Cart
  • ヤブヌマ [N.R.D.WORKS]
    Adventure
    ヤブヌマ
    N.R.D.WORKS
    1,100 JPY / $7.15 USD / 100pt(10%)
    藪沼のような男は、咲美のもっとも嫌うタイプである。 だからこそ僕は……、藪沼と咲美が…………交わることを妄想した。 ADV形式の一本道「寝取られ」ノベルです。
    Purchased: 2,649
    (981)
    (15)
    Release date : Dec/29/2009
    Cart
  • [Public Script] JK Knocked Unconscious By Aphrodisiac Pleasure Gets Creampied In A Toilet [School Voice]
    Voice / ASMR
    [Public Script] JK Knocked Unconscious By Aphrodisiac Pleasure Gets Creampied In A Toilet
    School Voice/いばら
    55 JPY 110 JPY / $0.36 USD$0.71 USD / 5pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    A molester on the train uses aphrodisiacs to heighten the sensuality of a high school girl, knock her out with pleasure, and then creampie r*pe her in a toilet afterwards.
    Purchased: 1,143
    (272)
    (14)
    Release date : Jun/20/2022
    Cart
  • Middle-aged Hero RPG ~R*pe Women With Your Authority, and Beat the Demon Lord~ [kagurado]
    Role-playing
    Middle-aged Hero RPG ~R*pe Women With Your Authority, and Beat the Demon Lord~
    kagurado
    1,430 JPY / $9.29 USD / 130pt(10%)
    This worthless middle-aged man awakens as a hero! The church tasks him with defeating the Demon Lord, but he seems more interested in using his new authority to r*pe cute girls. An orthodox-style HRPG.
    Purchased: 4,952
    (2,164)
    (14)
    Release date : May/18/2021
    Cart
  • L*li Schoolgirl Mana's Life Will End in Two Weeks ~With Ojisan~ [MoniKa]
    CG + Illustrations
    L*li Schoolgirl Mana's Life Will End in Two Weeks ~With Ojisan~
    MoniKa
    55 JPY 110 JPY / $0.36 USD$0.71 USD / 5pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    A l*li schoolgirl is made into an onahole via hypn*sis.
    Purchased: 337
    (128)
    (14)
    Release date : May/06/2020
    Cart
  • Girls Choose by Smegma Comic Anthology [Onanism]
    Manga
    Girls Choose by Smegma Comic Anthology
    Onanism
    440 JPY 880 JPY / $2.86 USD$5.72 USD / 40pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Five erotic manga artists have gathered to bring you some slutty stories about smegma!
    Purchased: 4,651
    (1,668)
    (13)
    Release date : Nov/08/2020
    Cart
  • Torima, Act 3. [Mi Po Z]
    Video
    Torima, Act 3.
    Mi Po Z
    550 JPY 1,100 JPY / $3.57 USD$7.15 USD / 50pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Two little girls go down on a grownup.
    Purchased: 2,660
    (1,298)
    (13)
    Release date : Sep/04/2011
    Cart
  • A martyr [ABARAYA]
    Simulation
    A martyr
    ABARAYA
    440 JPY 880 JPY / $2.86 USD$5.72 USD / 40pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Simulation Game: Sell the body of a young girl during the Industrial Revolution.
    Purchased: 1,565
    (1,002)
    (13)
    Release date : Oct/20/2010
    Cart
  • Special compensated dating [DaturaScript]
    Voice / ASMR
    Special compensated dating
    DaturaScript/秋野かえで
    660 JPY 1,320 JPY / $4.29 USD$8.58 USD / 60pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Two JK teens wonderfully voiced by Kaede, for your fapping pleasure. S, M types / 2:14:20 length
    Purchased: 1,827
    (981)
    (12)
    Release date : Mar/25/2016
    Cart
  • Standing postures for game creation Vol. 7 Men in business suit [Blue Forest]
    Illustration Materials
    Standing postures for game creation Vol. 7 Men in business suit
    Blue Forest
    660 JPY 1,100 JPY / $4.29 USD$7.15 USD / 60pt(10%)
    40% OFF ～Sep. 10, 13:59 (JST)
    This is a collection of raw imagery for use in game creation. For male characters.
    Purchased: 752
    (303)
    (12)
    All Ages
    Release date : Oct/24/2008
    Cart
  • Monsters of the Sea 2 Ver.1.0 [yosino]
    Video
    Monsters of the Sea 2 Ver.1.0
    yosino
    1,650 JPY / $10.72 USD / 150pt(10%)
    Yoshino Momiji proudly presents the sequel to Monster of the Sea series!
    Purchased: 5,278
    (2,107)
    (12)
    Release date : Nov/20/2010
    Cart
  • 開花させてはいけない [STARWORKS]
    Simulation
    開花させてはいけない
    STARWORKS
    1,925 JPY 2,750 JPY / $12.51 USD$17.87 USD / 175pt(10%)
    30% OFF ～Sep. 10, 13:59 (JST)
    爆乳妻と新生活を始めるも、やがて様々な劣等遺伝子たちと邂逅してしまう退廃的妻NTRーSLG
    Purchased: 7,507
    (2,530)
    (12)
    Release date : Jun/29/2023
    Cart
  • Copyright-free Voice! vol.01 Battle Voice. [Gentle Glasses]
    Voice / ASMR
    Copyright-free Voice! vol.01 Battle Voice.
    Gentle Glasses
    22 JPY 220 JPY / $0.14 USD$1.43 USD / 2pt(10%)
    90% OFF ～Sep. 10, 13:59 (JST)
    This is a set of copyright-free voice materials that are best suited to doujin works. Youth / Middle Age / Elderly
    Purchased: 162
    (50)
    (11)
    All Ages
    Release date : Jun/29/2018
    Cart
  • 隙間時間に正義のお仕事 [Quiet Northern Lands]
    Role-playing
    隙間時間に正義のお仕事
    Quiet Northern Lands
    1,760 JPY / $11.44 USD / 160pt(10%)
    美人で爆乳な2人の人妻の秘密のお仕事は、正義の組織『リリースラバーズ』の戦闘員!そんな2人が悪い男達によって、お仕事中でも日常生活でも、不貞三昧のスケベ女になるまでのお話。
    Purchased: 5,126
    (1,815)
    (11)
    Release date : Apr/15/2023
    Cart
  • 無知っ娘マオと堕落の街 [Entanglement]
    Role-playing
    無知っ娘マオと堕落の街
    Entanglement
    1,430 JPY / $9.29 USD / 130pt(10%)
    最強を目指す健康褐色少女マオは、相棒の少年テオと共に、強力な魔獣が闊歩する霊山『ブランクモント』で鍛錬するために『アナタイル王国』にある田舎町『ユールコーラム』へとやってくる。しかし、『ユールコーラム』は治安が悪いことで有名な町だった。道具屋のボンブや他の冒険者達から性的な目を向けられる中、無知なマオは綺麗な体のまま鍛錬を終えることが出来るのだろうか…。
    Purchased: 3,655
    (1,788)
    (11)
    Release date : May/13/2022
    Cart
  • My big brother's secret [Noraneko Kobo]
    CG + Illustrations
    My big brother's secret
    Noraneko Kobo
    495 JPY 990 JPY / $3.22 USD$6.43 USD / 45pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    22nd hentai CG collection featuring Min*mi-ke, featuring Haruka only.
    Purchased: 2,869
    (1,619)
    (11)
    Release date : Jun/17/2009
    Cart
  • Hey, do we really need these ropes? [mix fry]
    Manga
    Hey, do we really need these ropes?
    mix fry
    440 JPY / $2.86 USD / 40pt(10%)
    I just happened to meet an extremely pure girl. Moreover, she is so glamorous and cute... Well, I will try it out.
    Purchased: 1,299
    (508)
    (11)
    Release date : May/19/2018
    Cart
  • Why I Threw Away My Hot Boyfriend, and Married a Middle-aged Teacher [Village Survivor]
    CG + Illustrations
    Why I Threw Away My Hot Boyfriend, and Married a Middle-aged Teacher
    Village Survivor
    385 JPY 770 JPY / $2.50 USD$5 USD / 35pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Honami is a former shut-in who has just started going to correspondence school. However, what awaited her was violation at the hands of a delinquent, and eventual marriage to a middle-aged teacher.
    Purchased: 1,775
    (756)
    (11)
    Release date : Jun/20/2020
    Cart
  • タピオカミルク ～魅惑のシャワー室～ [Bingo Tarte]
    CG + Illustrations
    タピオカミルク ～魅惑のシャワー室～
    Bingo Tarte
    385 JPY 770 JPY / $2.50 USD$5 USD / 35pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    偶然出会った粘液生物との性交で身も心も虜になった○リっ子ナツミ。その生物の正体が町で見かける大嫌いなキモヲタだとも知らず・・。
    Purchased: 3,464
    (1,894)
    (11)
    Release date : Jul/24/2010
    Cart
  • Pregnancy Collection ~7 fleet girls~ [Nanoka H]
    CG + Illustrations
    Pregnancy Collection ~7 fleet girls~
    Nanoka H
    231 JPY 770 JPY / $1.50 USD$5 USD / 21pt(10%)
    70% OFF ～Sep. 10, 13:59 (JST)
    The result of having consensual loving sex with a perverted admiral is naturally... pregnancy and fleet girls sinking into a sea of pleasure.
    Purchased: 3,427
    (1,892)
    (11)
    Release date : Mar/19/2017
    Cart
  • Mura [yosino]
    Video
    Mura
    yosino
    1,540 JPY / $10.01 USD / 140pt(10%)
    "Ai" partakes in the local custom of becoming a woman.
    Purchased: 3,189
    (1,235)
    (11)
    Release date : Nov/26/2015
    Cart
  • Small factory mother and daughter [Ikenaiya Girl]
    CG + Illustrations
    Small factory mother and daughter
    Ikenaiya Girl
    770 JPY / $5 USD / 70pt(10%)
    The husband of a pretty wife and a kawaii daughter leaves them unprotected to fix the factory management problem...
    Purchased: 3,854
    (2,015)
    (11)
    Release date : Sep/14/2013
    Cart
  • Shouta (40) and the Summer of Second Chances [Chinjao Girl]
    CG + Illustrations
    Shouta (40) and the Summer of Second Chances
    Chinjao Girl
    880 JPY / $5.72 USD / 80pt(10%)
    CGs on the theme of a man who gets to re-live his youth.
    Purchased: 5,987
    (2,994)
    (11)
    Release date : Jul/11/2015
    Cart
  • Erotomaniac Camp - From Defiant Student to Submissive Bitch [Intrepid]
    CG + Illustrations
    Erotomaniac Camp - From Defiant Student to Submissive Bitch
    Intrepid
    385 JPY 770 JPY / $2.50 USD$5 USD / 35pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Because she helped her friend, Nana became a defiled whore of man's lust...
    Purchased: 7,534
    (4,015)
    (11)
    Release date : Dec/01/2010
    Cart
  • 【ド下品オホ声×ゲップの女神降臨】貧乳かわボ同人声優が泥酔オナニー実演!バイノーラル○○連発ドスケベげっぷ→汚声ギャップ連続絶頂!?【小机永遠】 [じつおな]
    Voice / ASMR
    【ド下品オホ声×ゲップの女神降臨】貧乳かわボ同人声優が泥酔オナニー実演!バイノーラル○○連発ドスケベげっぷ→汚声ギャップ連続絶頂!?【小机永遠】
    じつおな/小机永遠
    165 JPY 330 JPY / $1.07 USD$2.14 USD / 15pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    「泥酔×ゆるオホおっさん化オナニー」シリーズ第3回は、当サークル3回目の出演となるカワボ貧乳新人同人声優「小机永遠(こづくえとわ)」様によるオナニー実演です。今回は汚いおっさんになりきり、かわいい声してとんでもないド下品ぐちゅぐちゅオホオホ&爆音げっぷ大連発の超問題作…!身体の芯から気持ちよさそうなド淫乱下品おっさん化オナニー、ぜひお聴きください。
    Purchased: 695
    (91)
    (10)
    Release date : Apr/13/2024
    Cart
  • ROBOTCHESS FREE MATERIAL [Kurorarora]
    Illustration Materials
    ROBOTCHESS FREE MATERIAL
    Kurorarora
    550 JPY 1,100 JPY / $3.57 USD$7.15 USD / 50pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    Mecha and character materials for use in games, on social media, etc.
    Purchased: 588
    (232)
    (10)
    All Ages
    Release date : Apr/09/2020
    Cart
  • マシュの花嫁修業 [Manga Super]
    Manga
    マシュの花嫁修業
    Manga Super
    330 JPY 660 JPY / $2.14 USD$4.29 USD / 30pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    ひょんなことから領主様のお妃になることになったマ〇ュ。嫁ぐ前にしっかり「教育」を受けることに。教育係は絶倫チンポのおじさん妖精、朝から晩までセックス漬けの日々。記憶を無くしても身体にはスケベな本性が染みついちゃってます。
    Purchased: 2,651
    (829)
    (10)
    Release date : Jan/01/2022
    Cart
  • [Public Script] Filled With Semen By Older Men In The Toilet During A School Excursion... [School Voice]
    Voice / ASMR
    [Public Script] Filled With Semen By Older Men In The Toilet During A School Excursion...
    School Voice/いばら
    55 JPY 110 JPY / $0.36 USD$0.71 USD / 5pt(10%)
    50% OFF ～Sep. 10, 13:59 (JST)
    A girl is r*ped by a group of older men in the toilet during her school excursion...
    Purchased: 462
    (104)
    (10)
    Release date : Sep/11/2022
    Cart
Set works you wish to hide
Displaying  31~60  of 1615

Previous

Next

Narrow Search by Format

Users who browse Middle-aged Man are also interested in these genres.

About DLsite

DLsite is a 2D content download site specializing in doujinshi, manga, H games and more.

There's plenty of content for both PC and mobile device users!

Middle-aged Man is just one of the many genres of products we have!

New products are added every day!